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\n  \n 2023\n \n \n (4)\n \n \n
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\n \n\n \n \n \n \n \n \n OligoR: A Native HDX/MS Data Processing Application Dedicated to Oligonucleotides.\n \n \n \n \n\n\n \n Largy, E.; and Ranz, M.\n\n\n \n\n\n\n Analytical Chemistry,acs.analchem.3c01321. June 2023.\n \n\n\n\n
\n\n\n\n \n \n \"OligoR:Paper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n\n\n\n
\n 
@article{largy_oligor_2023,\n\ttitle = {{OligoR}: {A} {Native} {HDX}/{MS} {Data} {Processing} {Application} {Dedicated} to {Oligonucleotides}},\n\tcopyright = {All rights reserved},\n\tissn = {0003-2700, 1520-6882},\n\tshorttitle = {{OligoR}},\n\turl = {https://pubs.acs.org/doi/10.1021/acs.analchem.3c01321},\n\tdoi = {10.1021/acs.analchem.3c01321},\n\tlanguage = {en},\n\turldate = {2023-06-15},\n\tjournal = {Analytical Chemistry},\n\tauthor = {Largy, Eric and Ranz, Matthieu},\n\tmonth = jun,\n\tyear = {2023},\n\tkeywords = {\\#nosource},\n\tpages = {acs.analchem.3c01321},\n}\n\n
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\n \n\n \n \n \n \n \n \n New 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinazoline and 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinoline Derivatives: Synthesis and Biological Evaluation as Novel Anticancer Agents by Targeting G-Quadruplex.\n \n \n \n \n\n\n \n Guillon, J.; Le Borgne, M.; Milano, V.; Guédin-Beaurepaire, A.; Moreau, S.; Pinaud, N.; Ronga, L.; Savrimoutou, S.; Albenque-Rubio, S.; Marchivie, M.; Kalout, H.; Walker, C.; Chevallier, L.; Buré, C.; Largy, E.; Gabelica, V.; Mergny, J.; Baylot, V.; Ferrer, J.; Idrissi, Y.; Chevret, E.; Cappellen, D.; Desplat, V.; Schelz, Z.; and Zupkó, I.\n\n\n \n\n\n\n Pharmaceuticals, 17(1): 30. December 2023.\n \n\n\n\n
\n\n\n\n \n \n \"NewPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
\n 
@article{guillon_new_2023,\n\ttitle = {New 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinazoline and 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinoline {Derivatives}: {Synthesis} and {Biological} {Evaluation} as {Novel} {Anticancer} {Agents} by {Targeting} {G}-{Quadruplex}},\n\tvolume = {17},\n\tcopyright = {All rights reserved},\n\tissn = {1424-8247},\n\tshorttitle = {New 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinazoline and 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinoline {Derivatives}},\n\turl = {https://www.mdpi.com/1424-8247/17/1/30},\n\tdoi = {10.3390/ph17010030},\n\tabstract = {The syntheses of novel 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinazolines 12 and 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinolines 13 are reported here in six steps starting from various halogeno-quinazoline-2,4-(1H,3H)-diones or substituted anilines. The antiproliferative activities of the products were determined in vitro against a panel of breast (MCF-7 and MDA-MB-231), human adherent cervical (HeLa and SiHa), and ovarian (A2780) cell lines. Disubstituted 6- and 7-phenyl-bis(3-dimethylaminopropyl)aminomethylphenyl-quinazolines 12b, 12f, and 12i displayed the most interesting antiproliferative activities against six human cancer cell lines. In the series of quinoline derivatives, 6-phenyl-bis(3-dimethylaminopropyl)aminomethylphenylquinoline 13a proved to be the most active. G-quadruplexes (G4) stacked non-canonical nucleic acid structures found in specific G-rich DNA, or RNA sequences in the human genome are considered as potential targets for the development of anticancer agents. Then, as small aza-organic heterocyclic derivatives are well known to target and stabilize G4 structures, their ability to bind G4 structures have been determined through FRET melting, circular dichroism, and native mass spectrometry assays. Finally, telomerase inhibition ability has been also assessed using the MCF-7 cell line.},\n\tlanguage = {en},\n\tnumber = {1},\n\turldate = {2024-01-04},\n\tjournal = {Pharmaceuticals},\n\tauthor = {Guillon, Jean and Le Borgne, Marc and Milano, Vittoria and Guédin-Beaurepaire, Aurore and Moreau, Stéphane and Pinaud, Noël and Ronga, Luisa and Savrimoutou, Solène and Albenque-Rubio, Sandra and Marchivie, Mathieu and Kalout, Haouraa and Walker, Charley and Chevallier, Louise and Buré, Corinne and Largy, Eric and Gabelica, Valérie and Mergny, Jean-Louis and Baylot, Virginie and Ferrer, Jacky and Idrissi, Yamina and Chevret, Edith and Cappellen, David and Desplat, Vanessa and Schelz, Zsuzsanna and Zupkó, István},\n\tmonth = dec,\n\tyear = {2023},\n\tpages = {30},\n}\n\n
\n
\n\n\n
\n The syntheses of novel 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinazolines 12 and 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinolines 13 are reported here in six steps starting from various halogeno-quinazoline-2,4-(1H,3H)-diones or substituted anilines. The antiproliferative activities of the products were determined in vitro against a panel of breast (MCF-7 and MDA-MB-231), human adherent cervical (HeLa and SiHa), and ovarian (A2780) cell lines. Disubstituted 6- and 7-phenyl-bis(3-dimethylaminopropyl)aminomethylphenyl-quinazolines 12b, 12f, and 12i displayed the most interesting antiproliferative activities against six human cancer cell lines. In the series of quinoline derivatives, 6-phenyl-bis(3-dimethylaminopropyl)aminomethylphenylquinoline 13a proved to be the most active. G-quadruplexes (G4) stacked non-canonical nucleic acid structures found in specific G-rich DNA, or RNA sequences in the human genome are considered as potential targets for the development of anticancer agents. Then, as small aza-organic heterocyclic derivatives are well known to target and stabilize G4 structures, their ability to bind G4 structures have been determined through FRET melting, circular dichroism, and native mass spectrometry assays. Finally, telomerase inhibition ability has been also assessed using the MCF-7 cell line.\n
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\n \n\n \n \n \n \n \n \n A General Framework to Interpret Hydrogen–Deuterium Exchange Native Mass Spectrometry of G-Quadruplex DNA.\n \n \n \n \n\n\n \n Largy, E.; Ranz, M.; and Gabelica, V.\n\n\n \n\n\n\n Journal of the American Chemical Society,jacs.3c09365. December 2023.\n \n\n\n\n
\n\n\n\n \n \n \"APaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n  \n \n 2 downloads\n \n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
\n 
@article{largy_general_2023,\n\ttitle = {A {General} {Framework} to {Interpret} {Hydrogen}–{Deuterium} {Exchange} {Native} {Mass} {Spectrometry} of {G}-{Quadruplex} {DNA}},\n\tcopyright = {Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC-BY-NC-ND)},\n\tissn = {0002-7863, 1520-5126},\n\turl = {https://pubs.acs.org/doi/10.1021/jacs.3c09365},\n\tdoi = {10.1021/jacs.3c09365},\n\tlanguage = {en},\n\turldate = {2023-12-08},\n\tjournal = {Journal of the American Chemical Society},\n\tauthor = {Largy, Eric and Ranz, Matthieu and Gabelica, Valérie},\n\tmonth = dec,\n\tyear = {2023},\n\tpages = {jacs.3c09365},\n}\n\n
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\n \n\n \n \n \n \n \n \n DNA-HDXMS_XchangeDB: A dataset of Hydrogen-Deuterium eXchange native Mass Spectrometry experiments on DNA oligonucleotides.\n \n \n \n \n\n\n \n Largy, E.; Ranz, M.; and Gabelica, V.\n\n\n \n\n\n\n March 2023.\n \n\n\n\n
\n\n\n\n \n \n \"DNA-HDXMS_XchangeDB:Paper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n\n\n\n
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@misc{largy_eric_dna-hdxms_xchangedb_2023,\n\ttitle = {{DNA}-{HDXMS}\\_XchangeDB: {A} dataset of {Hydrogen}-{Deuterium} {eXchange} native {Mass} {Spectrometry} experiments on {DNA} oligonucleotides},\n\tcopyright = {Creative Commons Attribution 4.0 International, Open Access},\n\tshorttitle = {{DNA}-{HDXMS}\\_XchangeDB},\n\turl = {https://zenodo.org/record/7713144},\n\tdoi = {10.5281/ZENODO.7713144},\n\tabstract = {The DNA-HDXMS\\_XchangeDB dataset contains HDX/native MS exchange kinetics and metadata of a reference set of DNA oligonucleotides.},\n\tlanguage = {en},\n\turldate = {2023-03-16},\n\tpublisher = {Zenodo},\n\tauthor = {Largy, Eric and Ranz, Matthieu and Gabelica, Valérie},\n\tmonth = mar,\n\tyear = {2023},\n\tkeywords = {\\#nosource, DNA, nucleic acids, oligonucleotides, HDX, hydrogen deuterium exchange, mass spectrometry, kinetics},\n}\n\n
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\n The DNA-HDXMS_XchangeDB dataset contains HDX/native MS exchange kinetics and metadata of a reference set of DNA oligonucleotides.\n
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\n  \n 2022\n \n \n (1)\n \n \n
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\n \n\n \n \n \n \n \n \n Design, Synthesis, and Antiprotozoal Evaluation of New Promising 2,9-Bis[(substituted-aminomethyl)]-4,7-phenyl-1,10-phenanthroline Derivatives, a Potential Alternative Scaffold to Drug Efflux.\n \n \n \n \n\n\n \n Guillon, J.; Cohen, A.; Boudot, C.; Monic, S.; Savrimoutou, S.; Moreau, S.; Albenque-Rubio, S.; Lafon-Schmaltz, C.; Dassonville-Klimpt, A.; Mergny, J.; Ronga, L.; Bernabeu de Maria, M.; Lamarche, J.; Lago, C. D.; Largy, E.; Gabelica, V.; Moukha, S.; Dozolme, P.; Agnamey, P.; Azas, N.; Mullié, C.; Courtioux, B.; and Sonnet, P.\n\n\n \n\n\n\n Pathogens, 11(11): 1339. November 2022.\n \n\n\n\n
\n\n\n\n \n \n \"Design,Paper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
\n 
@article{guillon_design_2022,\n\ttitle = {Design, {Synthesis}, and {Antiprotozoal} {Evaluation} of {New} {Promising} 2,9-{Bis}[(substituted-aminomethyl)]-4,7-phenyl-1,10-phenanthroline {Derivatives}, a {Potential} {Alternative} {Scaffold} to {Drug} {Efflux}},\n\tvolume = {11},\n\tcopyright = {All rights reserved},\n\tissn = {2076-0817},\n\turl = {https://www.mdpi.com/2076-0817/11/11/1339},\n\tdoi = {10.3390/pathogens11111339},\n\tabstract = {A series of novel 2,9-bis[(substituted-aminomethyl)]-4,7-phenyl-1,10-phenanthroline derivatives was designed, synthesized, and evaluated in vitro against three protozoan parasites (Plasmodium falciparum, Leishmania donovani and Trypanosoma brucei brucei). Pharmacological results showed antiprotozoal activity with IC50 values in the sub and μM range. In addition, the in vitro cytotoxicity of these original molecules was assessed with human HepG2 cells. The substituted diphenylphenanthroline 1l was identified as the most potent antimalarial derivative with a ratio of cytotoxic to antiparasitic activities of 505.7 against the P. falciparum CQ-resistant strain W2. Against the promastigote forms of L. donovani, the phenanthrolines 1h, 1j, 1n and 1o were the most active with IC50 from 2.52 to 4.50 μM. The phenanthroline derivative 1o was also identified as the most potent trypanosomal candidate with a selectivity index (SI) of 91 on T. brucei brucei strain. FRET melting and native mass spectrometry experiments evidenced that the nitrogen heterocyclic derivatives bind the telomeric G-quadruplexes of P. falciparum and Trypanosoma. Moreover, as the telomeres of the parasites P. falciparum and Trypanosoma could be considered to be possible targets of this kind of nitrogen heterocyclic derivatives, their potential ability to stabilize the parasitic telomeric G-quadruplexes have been determined through the FRET melting assay and by native mass spectrometry.},\n\tlanguage = {en},\n\tnumber = {11},\n\turldate = {2023-01-20},\n\tjournal = {Pathogens},\n\tauthor = {Guillon, Jean and Cohen, Anita and Boudot, Clotilde and Monic, Sarah and Savrimoutou, Solène and Moreau, Stéphane and Albenque-Rubio, Sandra and Lafon-Schmaltz, Camille and Dassonville-Klimpt, Alexandra and Mergny, Jean-Louis and Ronga, Luisa and Bernabeu de Maria, Mikel and Lamarche, Jeremy and Lago, Cristina Dal and Largy, Eric and Gabelica, Valérie and Moukha, Serge and Dozolme, Pascale and Agnamey, Patrice and Azas, Nadine and Mullié, Catherine and Courtioux, Bertrand and Sonnet, Pascal},\n\tmonth = nov,\n\tyear = {2022},\n\tpages = {1339},\n}\n\n
\n
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\n A series of novel 2,9-bis[(substituted-aminomethyl)]-4,7-phenyl-1,10-phenanthroline derivatives was designed, synthesized, and evaluated in vitro against three protozoan parasites (Plasmodium falciparum, Leishmania donovani and Trypanosoma brucei brucei). Pharmacological results showed antiprotozoal activity with IC50 values in the sub and μM range. In addition, the in vitro cytotoxicity of these original molecules was assessed with human HepG2 cells. The substituted diphenylphenanthroline 1l was identified as the most potent antimalarial derivative with a ratio of cytotoxic to antiparasitic activities of 505.7 against the P. falciparum CQ-resistant strain W2. Against the promastigote forms of L. donovani, the phenanthrolines 1h, 1j, 1n and 1o were the most active with IC50 from 2.52 to 4.50 μM. The phenanthroline derivative 1o was also identified as the most potent trypanosomal candidate with a selectivity index (SI) of 91 on T. brucei brucei strain. FRET melting and native mass spectrometry experiments evidenced that the nitrogen heterocyclic derivatives bind the telomeric G-quadruplexes of P. falciparum and Trypanosoma. Moreover, as the telomeres of the parasites P. falciparum and Trypanosoma could be considered to be possible targets of this kind of nitrogen heterocyclic derivatives, their potential ability to stabilize the parasitic telomeric G-quadruplexes have been determined through the FRET melting assay and by native mass spectrometry.\n
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\n  \n 2021\n \n \n (5)\n \n \n
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\n \n\n \n \n \n \n \n \n Profiling, Relative Quantification, and Identification of Sialylated N-Linked Oligosaccharides by UPLC-FLR-ESI/MS After Derivatization with Fluorescent Anthranilamide.\n \n \n \n \n\n\n \n Butré, C. I.; Largy, E.; Cantais, F.; and Delobel, A.\n\n\n \n\n\n\n In Delobel, A., editor(s), Mass Spectrometry of Glycoproteins, volume 2271, pages 237–247. Springer US, New York, NY, 2021.\n Series Title: Methods in Molecular Biology\n\n\n\n
\n\n\n\n \n \n \"Profiling,Paper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
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@incollection{delobel_profiling_2021,\n\taddress = {New York, NY},\n\ttitle = {Profiling, {Relative} {Quantification}, and {Identification} of {Sialylated} {N}-{Linked} {Oligosaccharides} by {UPLC}-{FLR}-{ESI}/{MS} {After} {Derivatization} with {Fluorescent} {Anthranilamide}},\n\tvolume = {2271},\n\tcopyright = {All rights reserved},\n\tisbn = {978-1-07-161240-8 978-1-07-161241-5},\n\turl = {https://link.springer.com/10.1007/978-1-0716-1241-5_17},\n\tlanguage = {en},\n\turldate = {2024-01-05},\n\tbooktitle = {Mass {Spectrometry} of {Glycoproteins}},\n\tpublisher = {Springer US},\n\tauthor = {Butré, Claire I. and Largy, Eric and Cantais, Fabrice and Delobel, Arnaud},\n\teditor = {Delobel, Arnaud},\n\tyear = {2021},\n\tdoi = {10.1007/978-1-0716-1241-5_17},\n\tnote = {Series Title: Methods in Molecular Biology},\n\tpages = {237--247},\n}\n\n
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\n \n\n \n \n \n \n \n \n Profiling of N-Linked Oligosaccharides of a Glycoprotein by UPLC-FLR-ESI-MS After Derivatization with Fluorescent Anthranilamide.\n \n \n \n \n\n\n \n Butré, C. I.; Largy, E.; and Delobel, A.\n\n\n \n\n\n\n In Delobel, A., editor(s), Mass Spectrometry of Glycoproteins, volume 2271, pages 179–188. Springer US, New York, NY, 2021.\n Series Title: Methods in Molecular Biology\n\n\n\n
\n\n\n\n \n \n \"ProfilingPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
\n 
@incollection{delobel_profiling_2021-1,\n\taddress = {New York, NY},\n\ttitle = {Profiling of {N}-{Linked} {Oligosaccharides} of a {Glycoprotein} by {UPLC}-{FLR}-{ESI}-{MS} {After} {Derivatization} with {Fluorescent} {Anthranilamide}},\n\tvolume = {2271},\n\tcopyright = {All rights reserved},\n\tisbn = {978-1-07-161240-8 978-1-07-161241-5},\n\turl = {https://link.springer.com/10.1007/978-1-0716-1241-5_13},\n\tlanguage = {en},\n\turldate = {2024-01-05},\n\tbooktitle = {Mass {Spectrometry} of {Glycoproteins}},\n\tpublisher = {Springer US},\n\tauthor = {Butré, Claire I. and Largy, Eric and Delobel, Arnaud},\n\teditor = {Delobel, Arnaud},\n\tyear = {2021},\n\tdoi = {10.1007/978-1-0716-1241-5_13},\n\tnote = {Series Title: Methods in Molecular Biology},\n\tpages = {179--188},\n}\n\n
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\n \n\n \n \n \n \n \n \n Design, synthesis, and antiproliferative effect of 2,9‐bis[4‐(pyridinylalkylaminomethyl)phenyl]‐1,10‐phenanthroline derivatives on human leukemic cells by targeting G‐quadruplex.\n \n \n \n \n\n\n \n Guillon, J.; Denevault‐Sabourin, C.; Chevret, E.; Brachet‐Botineau, M.; Milano, V.; Guédin‐Beaurepaire, A.; Moreau, S.; Ronga, L.; Savrimoutou, S.; Rubio, S.; Ferrer, J.; Lamarche, J.; Mergny, J.; Viaud‐Massuard, M.; Ranz, M.; Largy, E.; Gabelica, V.; Rosu, F.; Gouilleux, F.; and Desplat, V.\n\n\n \n\n\n\n Archiv der Pharmazie, 354(8): 2000450. August 2021.\n \n\n\n\n
\n\n\n\n \n \n \"Design,Paper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n\n\n\n
\n 
@article{guillon_design_2021,\n\ttitle = {Design, synthesis, and antiproliferative effect of 2,9‐bis[4‐(pyridinylalkylaminomethyl)phenyl]‐1,10‐phenanthroline derivatives on human leukemic cells by targeting {G}‐quadruplex},\n\tvolume = {354},\n\tcopyright = {All rights reserved},\n\tissn = {0365-6233, 1521-4184},\n\turl = {https://onlinelibrary.wiley.com/doi/10.1002/ardp.202000450},\n\tdoi = {10.1002/ardp.202000450},\n\tabstract = {Abstract\n            \n              Current multiagent chemotherapy regimens have improved the cure rate in acute leukemia patients, but they are highly toxic and poorly efficient in relapsed patients. To improve the treatment approaches, new specific molecules are needed. The G‐quadruplexes (G4s), which are noncanonical nucleic acid structures found in specific guanine‐rich DNA or RNA, are involved in many cellular events, including control of gene expression. G4s are considered as targets for the development of anticancer agents. Heterocyclic molecules are well known to target and stabilize G4 structures. Thus, a new series of 2,9‐bis[(substituted‐aminomethyl)phenyl]‐1,10‐phenanthroline derivatives (\n              1a\n              –\n              i\n              ) was designed, synthesized, and evaluated against five human myeloid leukemia cell lines (K562, KU812, MV4‐11, HL60, and U937). Their ability to stabilize various oncogene promoter G4 structures (c‐MYC, BCL‐2, and K‐RAS) as well as the telomeric G4 was also determined through the fluorescence resonance energy transfer melting assay and native mass spectrometry. In addition, the more bioactive ligands\n              1g\n              –\n              i\n              were tested for telomerase activity in HuT78 and MV4‐11 protein extracts.},\n\tlanguage = {en},\n\tnumber = {8},\n\turldate = {2024-01-05},\n\tjournal = {Archiv der Pharmazie},\n\tauthor = {Guillon, Jean and Denevault‐Sabourin, Caroline and Chevret, Edith and Brachet‐Botineau, Marie and Milano, Vittoria and Guédin‐Beaurepaire, Aurore and Moreau, Stéphane and Ronga, Luisa and Savrimoutou, Solène and Rubio, Sandra and Ferrer, Jacky and Lamarche, Jeremy and Mergny, Jean‐Louis and Viaud‐Massuard, Marie‐Claude and Ranz, Matthieu and Largy, Eric and Gabelica, Valérie and Rosu, Frédéric and Gouilleux, Fabrice and Desplat, Vanessa},\n\tmonth = aug,\n\tyear = {2021},\n\tkeywords = {1, 10-phenanthroline, FRET melting, G-quadruplex, G4 ligands, antiproliferative activity, leukemia},\n\tpages = {2000450},\n}\n\n
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\n Abstract Current multiagent chemotherapy regimens have improved the cure rate in acute leukemia patients, but they are highly toxic and poorly efficient in relapsed patients. To improve the treatment approaches, new specific molecules are needed. The G‐quadruplexes (G4s), which are noncanonical nucleic acid structures found in specific guanine‐rich DNA or RNA, are involved in many cellular events, including control of gene expression. G4s are considered as targets for the development of anticancer agents. Heterocyclic molecules are well known to target and stabilize G4 structures. Thus, a new series of 2,9‐bis[(substituted‐aminomethyl)phenyl]‐1,10‐phenanthroline derivatives ( 1a – i ) was designed, synthesized, and evaluated against five human myeloid leukemia cell lines (K562, KU812, MV4‐11, HL60, and U937). Their ability to stabilize various oncogene promoter G4 structures (c‐MYC, BCL‐2, and K‐RAS) as well as the telomeric G4 was also determined through the fluorescence resonance energy transfer melting assay and native mass spectrometry. In addition, the more bioactive ligands 1g – i were tested for telomerase activity in HuT78 and MV4‐11 protein extracts.\n
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\n \n\n \n \n \n \n \n \n Locking up the AS1411 Aptamer with a Flanking Duplex: Towards an Improved Nucleolin-Targeting.\n \n \n \n \n\n\n \n Miranda, A.; Santos, T.; Largy, E.; and Cruz, C.\n\n\n \n\n\n\n Pharmaceuticals, 14(2): 121. February 2021.\n \n\n\n\n
\n\n\n\n \n \n \"LockingPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n \n \n \n \n\n\n\n
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@article{miranda_locking_2021,\n\ttitle = {Locking up the {AS1411} {Aptamer} with a {Flanking} {Duplex}: {Towards} an {Improved} {Nucleolin}-{Targeting}},\n\tvolume = {14},\n\tcopyright = {All rights reserved},\n\tissn = {1424-8247},\n\tshorttitle = {Locking up the {AS1411} {Aptamer} with a {Flanking} {Duplex}},\n\turl = {https://www.mdpi.com/1424-8247/14/2/121},\n\tdoi = {10.3390/ph14020121},\n\tabstract = {We have designed AS1411-N6, a derivative of the nucleolin (NCL)-binding aptamer AS1411, by adding six nucleotides to the 5′-end that are complementary to nucleotides at the 3′-end forcing it into a stem-loop structure. We evaluated by several biophysical techniques if AS1411-N6 can adopt one or more conformations, one of which allows NCL binding. We found a decrease of polymorphism of G-quadruplex (G4)-forming sequences comparing to AS1411 and the G4 formation in presence of K+ promotes the duplex folding. We also studied the binding properties of ligands TMPyP4, PhenDC3, PDS, 360A, and BRACO-19 in terms of stability, binding, topology maintenance of AS1411-N6, and NCL recognition. The melting experiments revealed promising stabilizer effects of PhenDC3, 360A, and TMPyP4, and the affinity calculations showed that 360A is the most prominent affinity ligand for AS1411-N6 and AS1411. The affinity determined between AS1411-N6 and NCL denoting a strong interaction and complex formation was assessed by PAGE in which the electrophoretic profile of AS1411-N6 showed bands of the dimeric form in the presence of the ligands and NCL.},\n\tlanguage = {en},\n\tnumber = {2},\n\turldate = {2024-01-05},\n\tjournal = {Pharmaceuticals},\n\tauthor = {Miranda, André and Santos, Tiago and Largy, Eric and Cruz, Carla},\n\tmonth = feb,\n\tyear = {2021},\n\tkeywords = {AS1411 derivative, DNA aptamers, G-quadruplex, biophysical characterization},\n\tpages = {121},\n}\n\n
\n
\n\n\n
\n We have designed AS1411-N6, a derivative of the nucleolin (NCL)-binding aptamer AS1411, by adding six nucleotides to the 5′-end that are complementary to nucleotides at the 3′-end forcing it into a stem-loop structure. We evaluated by several biophysical techniques if AS1411-N6 can adopt one or more conformations, one of which allows NCL binding. We found a decrease of polymorphism of G-quadruplex (G4)-forming sequences comparing to AS1411 and the G4 formation in presence of K+ promotes the duplex folding. We also studied the binding properties of ligands TMPyP4, PhenDC3, PDS, 360A, and BRACO-19 in terms of stability, binding, topology maintenance of AS1411-N6, and NCL recognition. The melting experiments revealed promising stabilizer effects of PhenDC3, 360A, and TMPyP4, and the affinity calculations showed that 360A is the most prominent affinity ligand for AS1411-N6 and AS1411. The affinity determined between AS1411-N6 and NCL denoting a strong interaction and complex formation was assessed by PAGE in which the electrophoretic profile of AS1411-N6 showed bands of the dimeric form in the presence of the ligands and NCL.\n
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\n \n\n \n \n \n \n \n \n Mass Spectrometry of Nucleic Acid Noncovalent Complexes.\n \n \n \n \n\n\n \n Largy, E.; König, A.; Ghosh, A.; Ghosh, D.; Benabou, S.; Rosu, F.; and Gabelica, V.\n\n\n \n\n\n\n Chemical Reviews, 122: 7720–7839. September 2021.\n \n\n\n\n
\n\n\n\n \n \n \"MassPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n  \n \n 2 downloads\n \n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
\n 
@article{largy_mass_2021,\n\ttitle = {Mass {Spectrometry} of {Nucleic} {Acid} {Noncovalent} {Complexes}},\n\tvolume = {122},\n\tcopyright = {All rights reserved},\n\tissn = {0009-2665, 1520-6890},\n\turl = {https://pubs.acs.org/doi/10.1021/acs.chemrev.1c00386},\n\tdoi = {10.1021/acs.chemrev.1c00386},\n\tlanguage = {en},\n\turldate = {2021-10-01},\n\tjournal = {Chemical Reviews},\n\tauthor = {Largy, Eric and König, Alexander and Ghosh, Anirban and Ghosh, Debasmita and Benabou, Sanae and Rosu, Frédéric and Gabelica, Valérie},\n\tmonth = sep,\n\tyear = {2021},\n\tpages = {7720--7839},\n}\n\n
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\n  \n 2020\n \n \n (1)\n \n \n
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\n \n\n \n \n \n \n \n \n Native Hydrogen/Deuterium Exchange Mass Spectrometry of Structured DNA Oligonucleotides.\n \n \n \n \n\n\n \n Largy, E.; and Gabelica, V.\n\n\n \n\n\n\n Analytical Chemistry, 92(6): 4402–4410. March 2020.\n \n\n\n\n
\n\n\n\n \n \n \"NativePaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
\n 
@article{largy_native_2020,\n\ttitle = {Native {Hydrogen}/{Deuterium} {Exchange} {Mass} {Spectrometry} of {Structured} {DNA} {Oligonucleotides}},\n\tvolume = {92},\n\tcopyright = {All rights reserved},\n\tissn = {0003-2700, 1520-6882},\n\turl = {https://pubs.acs.org/doi/10.1021/acs.analchem.9b05298},\n\tdoi = {10.1021/acs.analchem.9b05298},\n\tlanguage = {en},\n\tnumber = {6},\n\turldate = {2024-01-05},\n\tjournal = {Analytical Chemistry},\n\tauthor = {Largy, Eric and Gabelica, Valérie},\n\tmonth = mar,\n\tyear = {2020},\n\tpages = {4402--4410},\n}\n\n
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\n  \n 2019\n \n \n (1)\n \n \n
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\n \n\n \n \n \n \n \n \n Kinetic analysis of N -alkylaryl carboxamide hexitol nucleotides as substrates for evolved polymerases.\n \n \n \n \n\n\n \n Renders, M.; Dumbre, S.; Abramov, M.; Kestemont, D.; Margamuljana, L.; Largy, E.; Cozens, C.; Vandenameele, J.; Pinheiro, V. B; Toye, D.; Frère, J.; and Herdewijn, P.\n\n\n \n\n\n\n Nucleic Acids Research, 47(5): 2160–2168. March 2019.\n \n\n\n\n
\n\n\n\n \n \n \"KineticPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
\n 
@article{renders_kinetic_2019,\n\ttitle = {Kinetic analysis of \\textit{{N}} -alkylaryl carboxamide hexitol nucleotides as substrates for evolved polymerases},\n\tvolume = {47},\n\tcopyright = {All rights reserved},\n\tissn = {0305-1048, 1362-4962},\n\turl = {https://academic.oup.com/nar/article/47/5/2160/5304328},\n\tdoi = {10.1093/nar/gkz008},\n\tlanguage = {en},\n\tnumber = {5},\n\turldate = {2024-01-05},\n\tjournal = {Nucleic Acids Research},\n\tauthor = {Renders, Marleen and Dumbre, Shrinivas and Abramov, Mikhail and Kestemont, Donaat and Margamuljana, Lia and Largy, Eric and Cozens, Christopher and Vandenameele, Julie and Pinheiro, Vitor B and Toye, Dominique and Frère, Jean-Marie and Herdewijn, Piet},\n\tmonth = mar,\n\tyear = {2019},\n\tpages = {2160--2168},\n}\n\n
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\n  \n 2018\n \n \n (2)\n \n \n
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\n \n\n \n \n \n \n \n \n IL-7 receptor blockade blunts antigen-specific memory T cell responses and chronic inflammation in primates.\n \n \n \n \n\n\n \n Belarif, L.; Mary, C.; Jacquemont, L.; Mai, H. L.; Danger, R.; Hervouet, J.; Minault, D.; Thepenier, V.; Nerrière-Daguin, V.; Nguyen, E.; Pengam, S.; Largy, E.; Delobel, A.; Martinet, B.; Le Bas-Bernardet, S.; Brouard, S.; Soulillou, J.; Degauque, N.; Blancho, G.; Vanhove, B.; and Poirier, N.\n\n\n \n\n\n\n Nature Communications, 9(1): 4483. December 2018.\n ISBN: 2011/094259\n\n\n\n
\n\n\n\n \n \n \"IL-7Paper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n\n\n\n
\n 
@article{belarif_il-7_2018,\n\ttitle = {{IL}-7 receptor blockade blunts antigen-specific memory {T} cell responses and chronic inflammation in primates},\n\tvolume = {9},\n\tcopyright = {All rights reserved},\n\tissn = {2041-1723},\n\turl = {http://www.nature.com/articles/s41467-018-06804-y},\n\tdoi = {10.1038/s41467-018-06804-y},\n\tlanguage = {en},\n\tnumber = {1},\n\turldate = {2020-11-09},\n\tjournal = {Nature Communications},\n\tauthor = {Belarif, Lyssia and Mary, Caroline and Jacquemont, Lola and Mai, Hoa Le and Danger, Richard and Hervouet, Jeremy and Minault, David and Thepenier, Virginie and Nerrière-Daguin, Veronique and Nguyen, Elisabeth and Pengam, Sabrina and Largy, Eric and Delobel, Arnaud and Martinet, Bernard and Le Bas-Bernardet, Stéphanie and Brouard, Sophie and Soulillou, Jean-Paul and Degauque, Nicolas and Blancho, Gilles and Vanhove, Bernard and Poirier, Nicolas},\n\tmonth = dec,\n\tyear = {2018},\n\tpmcid = {PMC6203796},\n\tpmid = {30367166},\n\tnote = {ISBN: 2011/094259},\n\tkeywords = {Animals, Antibodies, Monoclonal, Chronic Disease, Clonal Deletion, Disease Models, Animal, Humans, Immunologic Memory, Inflammation, Interferon-gamma, Papio, Receptors, Interleukin-7, Signal Transduction, Skin, T-Lymphocytes},\n\tpages = {4483},\n}\n\n
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\n \n\n \n \n \n \n \n Epitope Mapping of an Interleukin Receptor for Three Therapeutic Antibodies by Hydrogen-Deuterium Exchange Mass Spectrometry.\n \n \n \n\n\n \n Cajot, C.; Delobel, A.; and Largy, E.\n\n\n \n\n\n\n LCGC: Special Issues, 16(4): 8–14. October 2018.\n \n\n\n\n
\n\n\n\n \n\n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n\n\n\n
\n 
@article{cajot_epitope_2018,\n\ttitle = {Epitope {Mapping} of an {Interleukin} {Receptor} for {Three} {Therapeutic} {Antibodies} by {Hydrogen}-{Deuterium} {Exchange} {Mass} {Spectrometry}},\n\tvolume = {16},\n\tcopyright = {All rights reserved},\n\tabstract = {The study of protein-protein interactions is critical in the development of biotherapeutics, to develop new candidates, to understand modes of actions, and to protect intellectual property. Among all the analytical techniques available for epitope mapping studies, hydrogen–deuterium exchange mass spectrometry (HDX-MS) is usually faster and easier to carry out. We present here the epitope mapping of three distinct monoclonal antibody (mAb) candidates targeting the same antigen, an interleukin receptor. The goal is to establish the binding mode of these mAbs, and explain possible differences observed for in vitro binding and in vivo function.},\n\tnumber = {4},\n\tjournal = {LCGC: Special Issues},\n\tauthor = {Cajot, Caroline and Delobel, Arnaud and Largy, Eric},\n\tmonth = oct,\n\tyear = {2018},\n\tkeywords = {\\#nosource, ⛔ No DOI found},\n\tpages = {8--14},\n}\n\n
\n
\n\n\n
\n The study of protein-protein interactions is critical in the development of biotherapeutics, to develop new candidates, to understand modes of actions, and to protect intellectual property. Among all the analytical techniques available for epitope mapping studies, hydrogen–deuterium exchange mass spectrometry (HDX-MS) is usually faster and easier to carry out. We present here the epitope mapping of three distinct monoclonal antibody (mAb) candidates targeting the same antigen, an interleukin receptor. The goal is to establish the binding mode of these mAbs, and explain possible differences observed for in vitro binding and in vivo function.\n
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\n  \n 2017\n \n \n (2)\n \n \n
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\n \n\n \n \n \n \n \n \n Orthogonal liquid chromatography–mass spectrometry methods for the comprehensive characterization of therapeutic glycoproteins, from released glycans to intact protein level.\n \n \n \n \n\n\n \n Largy, E.; Cantais, F.; Van Vyncht, G.; Beck, A.; and Delobel, A.\n\n\n \n\n\n\n Journal of Chromatography A, 1498: 128–146. May 2017.\n \n\n\n\n
\n\n\n\n \n \n \"OrthogonalPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n  \n \n 1 download\n \n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n \n \n\n\n\n
\n 
@article{largy_orthogonal_2017,\n\ttitle = {Orthogonal liquid chromatography–mass spectrometry methods for the comprehensive characterization of therapeutic glycoproteins, from released glycans to intact protein level},\n\tvolume = {1498},\n\tcopyright = {All rights reserved},\n\tissn = {00219673},\n\turl = {https://linkinghub.elsevier.com/retrieve/pii/S002196731730331X},\n\tdoi = {10.1016/j.chroma.2017.02.072},\n\tlanguage = {en},\n\turldate = {2024-01-05},\n\tjournal = {Journal of Chromatography A},\n\tauthor = {Largy, Eric and Cantais, Fabrice and Van Vyncht, Géry and Beck, Alain and Delobel, Arnaud},\n\tmonth = may,\n\tyear = {2017},\n\tkeywords = {high-resolution mass spectrometry, hydrophilic interaction chromatography, mixed-mode chromatography},\n\tpages = {128--146},\n}\n\n
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\n \n\n \n \n \n \n \n \n Unexpected position-dependent effects of ribose g-quartets in g-quadruplexes.\n \n \n \n \n\n\n \n Zhou, J.; Amrane, S.; Rosu, F.; Salgado, G. F.; Bian, Y.; Tateishi-Karimata, H.; Largy, E.; Korkut, D. N.; Bourdoncle, A.; Miyoshi, D.; Zhang, J.; Ju, H.; Wang, W.; Sugimoto, N.; Gabelica, V.; and Mergny, J. L.\n\n\n \n\n\n\n Journal of the American Chemical Society, 139(23): 7768–7779. June 2017.\n \n\n\n\n
\n\n\n\n \n \n \"UnexpectedPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
\n 
@article{Zhou2017,\n\ttitle = {Unexpected position-dependent effects of ribose g-quartets in g-quadruplexes},\n\tvolume = {139},\n\tcopyright = {All rights reserved},\n\tissn = {15205126},\n\turl = {http://pubs.acs.org/doi/abs/10.1021/jacs.7b00648},\n\tdoi = {10.1021/jacs.7b00648},\n\tabstract = {To understand the role of ribose G-quartets and how they affect the properties of G-quadruplex structures, we studied three systems in which one, two, three, or four deoxyribose G-quartets were substituted with ribose G-quartets. These systems were a parallel DNA intramolecular G-quadruplex d(TTGGGTGGGTTGGGTGGGTT) and two tetramolecular G-quadruplexes d(TGGGT) and d(TGGGGT). Thermal denaturation experiments revealed that ribose G-quartets have position-dependent and cumulative effects on G-quadruplex stability. An unexpected destabilization was observed when rG quartets were present at the 5'-end of the G stack. This observation challenges the general belief that RNA residues stabilize G-quadruplexes. Furthermore, in contrast to past proposals, hydration is not the main factor determining the stability of our RNA/DNA chimeric G-quadruplexes. Interestingly, the presence of rG residues in a central G-quartet facilitated the formation of additional tetramolecular G-quadruplex topologies showing positive circular dichroism signals at 295 nm. 2D NMR analysis of the tetramolecular TGgGGT (lower case indicates ribose) indicates that Gs in the 5'-most G-quartet adopt the syn conformation. These analyses highlight several new aspects of the role of ribose G-quartets on G-quadruplex structure and stability, and demonstrate that the positions of ribose residues are critical for tuning G-quadruplex properties.},\n\tnumber = {23},\n\tjournal = {Journal of the American Chemical Society},\n\tauthor = {Zhou, Jun and Amrane, Samir and Rosu, Frédéric and Salgado, Gilmar F. and Bian, Yunqiang and Tateishi-Karimata, Hisae and Largy, Eric and Korkut, Dursun Nizam and Bourdoncle, Anne and Miyoshi, Daisuke and Zhang, Jian and Ju, Huangxian and Wang, Wei and Sugimoto, Naoki and Gabelica, Valérie and Mergny, Jean-Louis Louis},\n\tmonth = jun,\n\tyear = {2017},\n\tpages = {7768--7779},\n}\n\n
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\n To understand the role of ribose G-quartets and how they affect the properties of G-quadruplex structures, we studied three systems in which one, two, three, or four deoxyribose G-quartets were substituted with ribose G-quartets. These systems were a parallel DNA intramolecular G-quadruplex d(TTGGGTGGGTTGGGTGGGTT) and two tetramolecular G-quadruplexes d(TGGGT) and d(TGGGGT). Thermal denaturation experiments revealed that ribose G-quartets have position-dependent and cumulative effects on G-quadruplex stability. An unexpected destabilization was observed when rG quartets were present at the 5'-end of the G stack. This observation challenges the general belief that RNA residues stabilize G-quadruplexes. Furthermore, in contrast to past proposals, hydration is not the main factor determining the stability of our RNA/DNA chimeric G-quadruplexes. Interestingly, the presence of rG residues in a central G-quartet facilitated the formation of additional tetramolecular G-quadruplex topologies showing positive circular dichroism signals at 295 nm. 2D NMR analysis of the tetramolecular TGgGGT (lower case indicates ribose) indicates that Gs in the 5'-most G-quartet adopt the syn conformation. These analyses highlight several new aspects of the role of ribose G-quartets on G-quadruplex structure and stability, and demonstrate that the positions of ribose residues are critical for tuning G-quadruplex properties.\n
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\n  \n 2016\n \n \n (3)\n \n \n
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\n \n\n \n \n \n \n \n \n Quadruplex turncoats: Cation-dependent folding and stability of quadruplex-dna double switches.\n \n \n \n \n\n\n \n Largy, E.; Marchand, A.; Amrane, S.; Gabelica, V.; and Mergny, J.\n\n\n \n\n\n\n Journal of the American Chemical Society, 138(8): 2780–2792. March 2016.\n \n\n\n\n
\n\n\n\n \n \n \"QuadruplexPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
\n 
@article{Largy2016,\n\ttitle = {Quadruplex turncoats: {Cation}-dependent folding and stability of quadruplex-dna double switches},\n\tvolume = {138},\n\tcopyright = {All rights reserved},\n\tissn = {0002-7863},\n\turl = {http://pubs.acs.org/doi/abs/10.1021/jacs.5b13130},\n\tdoi = {10.1021/jacs.5b13130},\n\tabstract = {© 2016 American Chemical Society. Quadruplex (G4) nucleic acids, a family of secondary structures formed by guanine-rich sequences, exhibit an important structural polymorphism. We demonstrate here that G-rich DNA sequences may function as a double switch based on different triggers, provided that their quadruplex structures and stability display a high dependence on cation nature and concentration. A first switch is based on a remarkable antiparallel-to-parallel conversion, taking place in a few seconds at room temperature by addition of low KCl amounts to a sodium-rich sample. The second switch involves the conversion of alternative antiparallel quadruplex structures binding only one cation, formed in the presence of sub-millimolar potassium or strontium concentrations, to parallel structures by increasing the cation concentration. Incidentally, extremely low K+ or Sr2+ concentrations (≤5 equiv) are sufficient to induce G4 formation in a buffer devoid of other G4-promoting cations, and we suggest that the alternative structures observed contain only two tetrads. Such DNA systems are biological relevant targets, can be used in nanotechnology applications, and are valuable methodological tools for understanding DNA quadruplex folding, notably at low cation concentrations. We demonstrate that this behavior is not restricted to a narrow set of sequences but can also be found for other G-quadruplex-forming motifs, arguing for widespread applications.},\n\tnumber = {8},\n\tjournal = {Journal of the American Chemical Society},\n\tauthor = {Largy, Eric and Marchand, Adrien and Amrane, Samir and Gabelica, Valérie and Mergny, Jean-Louis},\n\tmonth = mar,\n\tyear = {2016},\n\tpmid = {26837276},\n\tpages = {2780--2792},\n}\n\n
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\n © 2016 American Chemical Society. Quadruplex (G4) nucleic acids, a family of secondary structures formed by guanine-rich sequences, exhibit an important structural polymorphism. We demonstrate here that G-rich DNA sequences may function as a double switch based on different triggers, provided that their quadruplex structures and stability display a high dependence on cation nature and concentration. A first switch is based on a remarkable antiparallel-to-parallel conversion, taking place in a few seconds at room temperature by addition of low KCl amounts to a sodium-rich sample. The second switch involves the conversion of alternative antiparallel quadruplex structures binding only one cation, formed in the presence of sub-millimolar potassium or strontium concentrations, to parallel structures by increasing the cation concentration. Incidentally, extremely low K+ or Sr2+ concentrations (≤5 equiv) are sufficient to induce G4 formation in a buffer devoid of other G4-promoting cations, and we suggest that the alternative structures observed contain only two tetrads. Such DNA systems are biological relevant targets, can be used in nanotechnology applications, and are valuable methodological tools for understanding DNA quadruplex folding, notably at low cation concentrations. We demonstrate that this behavior is not restricted to a narrow set of sequences but can also be found for other G-quadruplex-forming motifs, arguing for widespread applications.\n
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\n \n\n \n \n \n \n \n \n Role of Alkali Metal Ions in G-Quadruplex Nucleic Acid Structure and Stability.\n \n \n \n \n\n\n \n Largy, E.; Mergny, J.; and Gabelica, V.\n\n\n \n\n\n\n In Sigel, A.; Sigel, H.; and Sigel, R. K. O., editor(s), The Alkali Metal Ions: Their Role for Life, volume 16, pages 203–258. Springer International Publishing, Cham, 2016.\n seriesTitle: Metal Ions in Life Sciences\n\n\n\n
\n\n\n\n \n \n \"RolePaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n  \n \n 1 download\n \n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
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@incollection{sigel_role_2016,\n\taddress = {Cham},\n\ttitle = {Role of {Alkali} {Metal} {Ions} in {G}-{Quadruplex} {Nucleic} {Acid} {Structure} and {Stability}},\n\tvolume = {16},\n\tcopyright = {All rights reserved},\n\tisbn = {978-3-319-21755-0 978-3-319-21756-7},\n\turl = {http://link.springer.com/10.1007/978-3-319-21756-7_7},\n\turldate = {2020-11-08},\n\tbooktitle = {The {Alkali} {Metal} {Ions}: {Their} {Role} for {Life}},\n\tpublisher = {Springer International Publishing},\n\tauthor = {Largy, Eric and Mergny, Jean-Louis and Gabelica, Valérie},\n\teditor = {Sigel, Astrid and Sigel, Helmut and Sigel, Roland K. O.},\n\tyear = {2016},\n\tdoi = {10.1007/978-3-319-21756-7_7},\n\tnote = {seriesTitle: Metal Ions in Life Sciences},\n\tpages = {203--258},\n}\n\n
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\n \n\n \n \n \n \n \n 2D-LC–MS for the analysis of monoclonal antibodies and antibody–drug conjugates in a regulated environment.\n \n \n \n\n\n \n Largy, E.; Catrain, A.; Van Vyncht, G.; and Delobel, A.\n\n\n \n\n\n\n LCGC: Special Issues, 14(2): 29–35. 2016.\n \n\n\n\n
\n\n\n\n \n\n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n\n\n\n
\n 
@article{van20162d,\n\ttitle = {{2D}-{LC}–{MS} for the analysis of monoclonal antibodies and antibody–drug conjugates in a regulated environment},\n\tvolume = {14},\n\tcopyright = {All rights reserved},\n\tnumber = {2},\n\tjournal = {LCGC: Special Issues},\n\tauthor = {Largy, Eric and Catrain, Anicet and Van Vyncht, Géry and Delobel, Arnaud},\n\tyear = {2016},\n\tkeywords = {\\#nosource, ⛔ No DOI found},\n\tpages = {29--35},\n}\n\n
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\n  \n 2014\n \n \n (2)\n \n \n
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\n \n \n
\n \n\n \n \n \n \n \n \n Shape matters: size-exclusion HPLC for the study of nucleic acid structural polymorphism.\n \n \n \n \n\n\n \n Largy, E.; and Mergny, J.\n\n\n \n\n\n\n Nucleic acids research, 42(19): e149. October 2014.\n \n\n\n\n
\n\n\n\n \n \n \"ShapePaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
\n 
@article{Largy2014,\n\ttitle = {Shape matters: size-exclusion {HPLC} for the study of nucleic acid structural polymorphism.},\n\tvolume = {42},\n\tcopyright = {All rights reserved},\n\tissn = {1362-4962},\n\turl = {http://nar.oxfordjournals.org/lookup/doi/10.1093/nar/gku751 http://www.ncbi.nlm.nih.gov/pubmed/25143531},\n\tdoi = {10.1093/nar/gku751},\n\tabstract = {In recent years, an increasing number of reports have been focused on the structure and biological role of non-canonical nucleic acid secondary structures. Many of these studies involve the use of oligonucleotides that can often adopt a variety of structures depending on the experimental conditions, and hence change the outcome of an assay. The knowledge of the structure(s) formed by oligonucleotides is thus critical to correctly interpret the results, and gain insight into the biological role of these particular sequences. Herein we demonstrate that size-exclusion HPLC (SE-HPLC) is a simple yet surprisingly powerful tool to quickly and effortlessly assess the secondary structure(s) formed by oligonucleotides. For the first time, an extensive calibration and validation of the use of SE-HPLC to confidently detect the presence of different species displaying various structure and/or molecularity, involving ¿110 oligonucleotides forming a variety of secondary structures (antiparallel, parallel, A-tract bent and mismatched duplexes, triplexes, G-quadruplexes and i-motifs, RNA stem loops), is performed. Moreover, we introduce simple metrics that allow the use of SE-HPLC without the need for a tedious calibration work. We show that the remarkable versatility of the method allows to quickly establish the influence of a number of experimental parameters on nucleic acid structuration and to operate on a wide range of oligonucleotide concentrations. Case studies are provided to clearly illustrate the all-terrain capabilities of SE-HPLC for oligonucleotide secondary structure analysis. Finally, this manuscript features a number of important observations contributing to a better understanding of nucleic acid structural polymorphism.},\n\tnumber = {19},\n\tjournal = {Nucleic acids research},\n\tauthor = {Largy, Eric and Mergny, Jean-Louis},\n\tmonth = oct,\n\tyear = {2014},\n\tpmid = {25143531},\n\tpages = {e149},\n}\n\n
\n
\n\n\n
\n In recent years, an increasing number of reports have been focused on the structure and biological role of non-canonical nucleic acid secondary structures. Many of these studies involve the use of oligonucleotides that can often adopt a variety of structures depending on the experimental conditions, and hence change the outcome of an assay. The knowledge of the structure(s) formed by oligonucleotides is thus critical to correctly interpret the results, and gain insight into the biological role of these particular sequences. Herein we demonstrate that size-exclusion HPLC (SE-HPLC) is a simple yet surprisingly powerful tool to quickly and effortlessly assess the secondary structure(s) formed by oligonucleotides. For the first time, an extensive calibration and validation of the use of SE-HPLC to confidently detect the presence of different species displaying various structure and/or molecularity, involving ¿110 oligonucleotides forming a variety of secondary structures (antiparallel, parallel, A-tract bent and mismatched duplexes, triplexes, G-quadruplexes and i-motifs, RNA stem loops), is performed. Moreover, we introduce simple metrics that allow the use of SE-HPLC without the need for a tedious calibration work. We show that the remarkable versatility of the method allows to quickly establish the influence of a number of experimental parameters on nucleic acid structuration and to operate on a wide range of oligonucleotide concentrations. Case studies are provided to clearly illustrate the all-terrain capabilities of SE-HPLC for oligonucleotide secondary structure analysis. Finally, this manuscript features a number of important observations contributing to a better understanding of nucleic acid structural polymorphism.\n
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\n \n\n \n \n \n \n \n \n Quadruplexes are everywhere!.\n \n \n \n \n\n\n \n Amrane, S.; Bedrat, A.; Renaud De La Faverie, A.; Zhou, J.; Mendoza, O.; De Rache, A.; Guedin, A.; Largy, E.; Amor, S.; Salgado, G.; Bourdoncle, A.; Yatsunyk, L. A.; and Mergny, J.\n\n\n \n\n\n\n In Collection Symposium Series, pages 62–65, Český Krumlov, 2014. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic\n \n\n\n\n
\n\n\n\n \n \n \"QuadruplexesPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n\n\n\n
\n 
@inproceedings{amrane_quadruplexes_2014,\n\taddress = {Český Krumlov},\n\ttitle = {Quadruplexes are everywhere!},\n\tcopyright = {All rights reserved},\n\tisbn = {978-80-86241-50-0},\n\turl = {http://cccc.uochb.cas.cz/symposium_series/14/62/},\n\tdoi = {10.1135/css201414062},\n\tlanguage = {en},\n\turldate = {2020-11-08},\n\tbooktitle = {Collection {Symposium} {Series}},\n\tpublisher = {Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic},\n\tauthor = {Amrane, Samir and Bedrat, Amina and Renaud De La Faverie, Amandine and Zhou, Jun and Mendoza, Oscar and De Rache, Aurore and Guedin, Aurore and Largy, Eric and Amor, Souheila and Salgado, Gilmar and Bourdoncle, Anne and Yatsunyk, Liliya A. and Mergny, Jean-Louis},\n\tyear = {2014},\n\tkeywords = {\\#nosource},\n\tpages = {62--65},\n}\n\n
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\n  \n 2013\n \n \n (1)\n \n \n
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\n \n\n \n \n \n \n \n Asymmetric distyrylpyridinium dyes as red-emitting fluorescent probes for quadruplex DNA.\n \n \n \n\n\n \n Xie, X.; Choi, B.; Largy, E.; Guillot, R.; Granzhan, A.; and Teulade-Fichou, M.\n\n\n \n\n\n\n Chemistry - A European Journal, 19: 1214–1226. 2013.\n \n\n\n\n
\n\n\n\n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n\n\n\n
\n 
@article{xie_asymmetric_2013,\n\ttitle = {Asymmetric distyrylpyridinium dyes as red-emitting fluorescent probes for quadruplex {DNA}.},\n\tvolume = {19},\n\tcopyright = {All rights reserved},\n\tdoi = {10.1002/chem.201203710},\n\tabstract = {The interactions of three cationic distyryl dyes, namely 2,4-bis(4-dimethylaminostyryl)-1-methylpyridinium (1a), its derivative with a quaternary aminoalkyl chain (1b), and the symmetric 2,6-bis(4-dimethylaminostyryl)-1-methylpyridinium (2a), with several quadruplex and duplex nucleic acids were studied with the aim to establish the influence of the geometry of the dyes on their DNA-binding and DNA-probing properties. The results from spectrofluorimetric titrations and thermal denaturation experiments provide evidence that asymmetric (2,4-disubstituted) dyes 1a and 1b bind to quadruplex DNA structures with a near-micromolar affinity and a fair selectivity with respect to double-stranded (ds) DNA K(a)(G4)/K(a)(ds)=2.5-8.4. At the same time, the fluorescence of both dyes is selectively increased in the presence of quadruplex DNAs (more than 80-100-fold in the case of human telomeric quadruplex), even in the presence of an excess of competing double-stranded DNA. This optical selectivity allows these dyes to be used as quadruplex-DNA-selective probes in solution and stains in polyacrylamide gels. In contrast, the symmetric analogue 2a displays a strong binding preference for double-stranded DNA K(a) (ds)/K(a) (G4)=40-100), presumably due to binding in the minor groove. In addition, 2a is not able to discriminate between quadruplex and duplex DNA, as its fluorescence is increased equally well (20-50-fold) in the presence of both structures. This study emphasizes and rationalizes the strong impact of subtle structural variations on both DNA-recognition properties and fluorimetric response of organic dyes.},\n\tjournal = {Chemistry - A European Journal},\n\tauthor = {Xie, Xiao and Choi, Bina and Largy, Eric and Guillot, Régis and Granzhan, Anton and Teulade-Fichou, Marie-Paule},\n\tyear = {2013},\n\tpmid = {23292703},\n\tkeywords = {Base Sequence, Crystallography, Fluorescent Dyes, Fluorescent Dyes: chemical synthesis, Fluorescent Dyes: chemistry, Fluorometry, G-Quadruplexes, Kinetics, Molecular Conformation, Pyridinium Compounds, Pyridinium Compounds: chemistry, X-Ray, sumo},\n\tpages = {1214--1226},\n}\n\n
\n
\n\n\n
\n The interactions of three cationic distyryl dyes, namely 2,4-bis(4-dimethylaminostyryl)-1-methylpyridinium (1a), its derivative with a quaternary aminoalkyl chain (1b), and the symmetric 2,6-bis(4-dimethylaminostyryl)-1-methylpyridinium (2a), with several quadruplex and duplex nucleic acids were studied with the aim to establish the influence of the geometry of the dyes on their DNA-binding and DNA-probing properties. The results from spectrofluorimetric titrations and thermal denaturation experiments provide evidence that asymmetric (2,4-disubstituted) dyes 1a and 1b bind to quadruplex DNA structures with a near-micromolar affinity and a fair selectivity with respect to double-stranded (ds) DNA K(a)(G4)/K(a)(ds)=2.5-8.4. At the same time, the fluorescence of both dyes is selectively increased in the presence of quadruplex DNAs (more than 80-100-fold in the case of human telomeric quadruplex), even in the presence of an excess of competing double-stranded DNA. This optical selectivity allows these dyes to be used as quadruplex-DNA-selective probes in solution and stains in polyacrylamide gels. In contrast, the symmetric analogue 2a displays a strong binding preference for double-stranded DNA K(a) (ds)/K(a) (G4)=40-100), presumably due to binding in the minor groove. In addition, 2a is not able to discriminate between quadruplex and duplex DNA, as its fluorescence is increased equally well (20-50-fold) in the presence of both structures. This study emphasizes and rationalizes the strong impact of subtle structural variations on both DNA-recognition properties and fluorimetric response of organic dyes.\n
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\n
\n  \n 2012\n \n \n (6)\n \n \n
\n
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\n \n\n \n \n \n \n \n \n Screening of a Chemical Library by HT-G4-FID for Discovery of Selective G-quadruplex Binders.\n \n \n \n \n\n\n \n Largy, E.; Saettel, N.; Hamon, F.; Dubruille, S.; and Teulade-Fichou, M.\n\n\n \n\n\n\n Current Pharmaceutical Design, 18(14): 1992–2001. March 2012.\n \n\n\n\n
\n\n\n\n \n \n \"ScreeningPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
\n 
@article{largy_screening_2012,\n\ttitle = {Screening of a {Chemical} {Library} by {HT}-{G4}-{FID} for {Discovery} of {Selective} {G}-quadruplex {Binders}},\n\tvolume = {18},\n\tcopyright = {All rights reserved},\n\tissn = {13816128},\n\turl = {http://www.eurekaselect.com/openurl/content.php?genre=article&issn=1381-6128&volume=18&issue=14&spage=1992},\n\tdoi = {10.2174/138161212799958350},\n\tlanguage = {en},\n\tnumber = {14},\n\turldate = {2024-01-05},\n\tjournal = {Current Pharmaceutical Design},\n\tauthor = {Largy, Eric and Saettel, Nicolas and Hamon, Florian and Dubruille, Sylvie and Teulade-Fichou, Marie-Paule},\n\tmonth = mar,\n\tyear = {2012},\n\tpages = {1992--2001},\n}\n\n
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\n \n\n \n \n \n \n \n \n Visualizing the Quadruplex: From Fluorescent Ligands to Light-Up Probes.\n \n \n \n \n\n\n \n Largy, E.; Granzhan, A.; Hamon, F.; Verga, D.; and Teulade-Fichou, M.\n\n\n \n\n\n\n In Chaires, J. B.; and Graves, D., editor(s), Quadruplex Nucleic Acids, volume 330, pages 111–177. Springer Berlin Heidelberg, Berlin, Heidelberg, 2012.\n Series Title: Topics in Current Chemistry\n\n\n\n
\n\n\n\n \n \n \"VisualizingPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
\n 
@incollection{chaires_visualizing_2012,\n\taddress = {Berlin, Heidelberg},\n\ttitle = {Visualizing the {Quadruplex}: {From} {Fluorescent} {Ligands} to {Light}-{Up} {Probes}},\n\tvolume = {330},\n\tcopyright = {All rights reserved},\n\tisbn = {978-3-642-34742-9 978-3-642-34743-6},\n\tshorttitle = {Visualizing the {Quadruplex}},\n\turl = {https://link.springer.com/10.1007/128_2012_346},\n\tlanguage = {en},\n\turldate = {2024-01-05},\n\tbooktitle = {Quadruplex {Nucleic} {Acids}},\n\tpublisher = {Springer Berlin Heidelberg},\n\tauthor = {Largy, Eric and Granzhan, Anton and Hamon, Florian and Verga, Daniela and Teulade-Fichou, Marie-Paule},\n\teditor = {Chaires, Jonathan B. and Graves, David},\n\tyear = {2012},\n\tdoi = {10.1007/128_2012_346},\n\tnote = {Series Title: Topics in Current Chemistry},\n\tpages = {111--177},\n}\n\n
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\n \n\n \n \n \n \n \n \n Cationic pentaheteroaryls as selective G-quadruplex ligands by solvent-free microwave-assisted synthesis.\n \n \n \n \n\n\n \n Petenzi, M.; Verga, D.; Largy, E.; Hamon, F.; Doria, F.; Teulade-Fichou, M.; Guédin, A.; Mergny, J.; Mella, M.; and Freccero, M.\n\n\n \n\n\n\n Chemistry - A European Journal, 18(45): 14487–96. November 2012.\n \n\n\n\n
\n\n\n\n \n \n \"CationicPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n\n\n\n
\n 
@article{Petenzi2012,\n\ttitle = {Cationic pentaheteroaryls as selective {G}-quadruplex ligands by solvent-free microwave-assisted synthesis.},\n\tvolume = {18},\n\tcopyright = {All rights reserved},\n\tissn = {1521-3765},\n\turl = {http://doi.wiley.com/10.1002/chem.201202097 http://www.ncbi.nlm.nih.gov/pubmed/22996572},\n\tdoi = {10.1002/chem.201202097},\n\tabstract = {We report herein a solvent-free and microwaved-assisted synthesis of several water soluble acyclic pentaheteroaryls containing 1,2,4-oxadiazole moieties (1-7). Their binding interactions with DNA quadruplex structures were thoroughly investigated by FRET melting, fluorescent intercalator displacement assay (G4-FID) and CD spectroscopy. Among the G-quadruplexes considered, attention was focused on telomeric repeats together with the proto-oncogenic c-kit sequences and the c-myc oncogene promoter. Compound 1, and to a lesser extent 2 and 5, preferentially stabilise an antiparallel structure of the telomeric DNA motif, and exhibit an opposite binding behaviour to structurally related polyoxazole (TOxaPy), and do not bind duplex DNA. The efficiency and selectivity of the binding process was remarkably controlled by the structure of the solubilising moieties.},\n\tnumber = {45},\n\tjournal = {Chemistry - A European Journal},\n\tauthor = {Petenzi, Michele and Verga, Daniela and Largy, Eric and Hamon, Florian and Doria, Filippo and Teulade-Fichou, Marie-Paule and Guédin, Aurore and Mergny, Jean-Louis and Mella, Mariella and Freccero, Mauro},\n\tmonth = nov,\n\tyear = {2012},\n\tpmid = {22996572},\n\tkeywords = {1, 2, 4-oxadiazoles, Cations, Cations: chemistry, Circular Dichroism, Fluorescence Resonance Energy Transfer, Fluorescent Dyes, Fluorescent Dyes: chemistry, G-Quadruplexes, Ligands, Microwaves, Oxadiazoles, Oxadiazoles: chemistry, Water, Water: chemistry},\n\tpages = {14487--96},\n}\n\n
\n
\n\n\n
\n We report herein a solvent-free and microwaved-assisted synthesis of several water soluble acyclic pentaheteroaryls containing 1,2,4-oxadiazole moieties (1-7). Their binding interactions with DNA quadruplex structures were thoroughly investigated by FRET melting, fluorescent intercalator displacement assay (G4-FID) and CD spectroscopy. Among the G-quadruplexes considered, attention was focused on telomeric repeats together with the proto-oncogenic c-kit sequences and the c-myc oncogene promoter. Compound 1, and to a lesser extent 2 and 5, preferentially stabilise an antiparallel structure of the telomeric DNA motif, and exhibit an opposite binding behaviour to structurally related polyoxazole (TOxaPy), and do not bind duplex DNA. The efficiency and selectivity of the binding process was remarkably controlled by the structure of the solubilising moieties.\n
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\n \n\n \n \n \n \n \n \n Screening for Quadruplex Binding Ligands: A Game of Chance?.\n \n \n \n \n\n\n \n Largy, E.; and Teulade-Fichou, M.\n\n\n \n\n\n\n In Spindler, L.; and Fritzsche, W., editor(s), Guanine Quartets, pages 248–262. Royal Society of Chemistry, Cambridge, 2012.\n \n\n\n\n
\n\n\n\n \n \n \"ScreeningPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
\n 
@incollection{spindler_screening_2012,\n\taddress = {Cambridge},\n\ttitle = {Screening for {Quadruplex} {Binding} {Ligands}: {A} {Game} of {Chance}?},\n\tcopyright = {All rights reserved},\n\tisbn = {978-1-84973-460-8},\n\tshorttitle = {Screening for {Quadruplex} {Binding} {Ligands}},\n\turl = {http://ebook.rsc.org/?DOI=10.1039/9781849736954-00248},\n\tlanguage = {en},\n\turldate = {2020-11-08},\n\tbooktitle = {Guanine {Quartets}},\n\tpublisher = {Royal Society of Chemistry},\n\tauthor = {Largy, E. and Teulade-Fichou, M.-P.},\n\teditor = {Spindler, Lea and Fritzsche, Wolfgang},\n\tyear = {2012},\n\tdoi = {10.1039/9781849736954-00248},\n\tpages = {248--262},\n}\n\n
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\n\n\n\n
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\n \n\n \n \n \n \n \n \n A streptavidin paramagnetic-particle based competition assay for the evaluation of the optical selectivity of quadruplex nucleic acid fluorescent probes.\n \n \n \n \n\n\n \n Largy, E.; Hamon, F.; and Teulade-Fichou, M.\n\n\n \n\n\n\n Methods, 57(1): 129–137. May 2012.\n publisher: Elsevier Inc.\n\n\n\n
\n\n\n\n \n \n \"APaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n\n\n\n
\n 
@article{largy_streptavidin_2012,\n\ttitle = {A streptavidin paramagnetic-particle based competition assay for the evaluation of the optical selectivity of quadruplex nucleic acid fluorescent probes},\n\tvolume = {57},\n\tcopyright = {All rights reserved},\n\tissn = {10462023},\n\turl = {https://linkinghub.elsevier.com/retrieve/pii/S1046202312000321},\n\tdoi = {10.1016/j.ymeth.2012.02.008},\n\tabstract = {Although quadruplex nucleic acids are thought to be involved in many biological processes, they are massively overwhelmed by duplex DNA in the cell. Small molecules, able to probe quadruplex nucleic acids with high optical selectivity, could possibly achieve the visualization of these processes. The aim of the method described herein is to evaluate quickly the optical selectivity of quadruplex nucleic acid probes, in isothermal conditions, using widely available materials, small quantities of oligonucleotides and virtually any kind and quantity of biological competitor. The assay relies on the use of streptavidin-coated paramagnetic particles and biotinylated quadruplex forming oligonucleotides, allowing a quick and easy separation of the quadruplex target from the competitor. In the present study, two quadruplex nucleic acids (the DNA and RNA human telomeric repeats) have been used as targets while a duplex DNA oligonucleotide, total DNA, total RNA, another quadruplex nucleic acid and a protein have been used as competitors. The optical selectivity of various probes, displaying different photophysical properties and binding selectivities, has been successfully examined, allowing the identification of a best candidate for further cell microscopy experiments. This assay allows a quick and reliable assessment of the labeling properties of a quadruplex binder in cellular environment conditions. It is an interesting alternative to gel electrophoresis experiments since it is performed in solution, has a well-resolved separation system and allows easy quantifications.},\n\tlanguage = {en},\n\tnumber = {1},\n\turldate = {2020-11-09},\n\tjournal = {Methods},\n\tauthor = {Largy, Eric and Hamon, Florian and Teulade-Fichou, Marie-Paule},\n\tmonth = may,\n\tyear = {2012},\n\tpmid = {22406492},\n\tnote = {publisher: Elsevier Inc.},\n\tkeywords = {DNA, DNA: chemistry, Fluorescent Dyes, Fluorescent Dyes: chemistry, Fluorescent probe, G-Quadruplexes, G-quadruplex, Humans, Nucleic acids, Oligonucleotides, Oligonucleotides: chemistry, Param, RNA, RNA: chemistry, Streptavidin, Streptavidin: chemistry},\n\tpages = {129--137},\n}\n\n
\n
\n\n\n
\n Although quadruplex nucleic acids are thought to be involved in many biological processes, they are massively overwhelmed by duplex DNA in the cell. Small molecules, able to probe quadruplex nucleic acids with high optical selectivity, could possibly achieve the visualization of these processes. The aim of the method described herein is to evaluate quickly the optical selectivity of quadruplex nucleic acid probes, in isothermal conditions, using widely available materials, small quantities of oligonucleotides and virtually any kind and quantity of biological competitor. The assay relies on the use of streptavidin-coated paramagnetic particles and biotinylated quadruplex forming oligonucleotides, allowing a quick and easy separation of the quadruplex target from the competitor. In the present study, two quadruplex nucleic acids (the DNA and RNA human telomeric repeats) have been used as targets while a duplex DNA oligonucleotide, total DNA, total RNA, another quadruplex nucleic acid and a protein have been used as competitors. The optical selectivity of various probes, displaying different photophysical properties and binding selectivities, has been successfully examined, allowing the identification of a best candidate for further cell microscopy experiments. This assay allows a quick and reliable assessment of the labeling properties of a quadruplex binder in cellular environment conditions. It is an interesting alternative to gel electrophoresis experiments since it is performed in solution, has a well-resolved separation system and allows easy quantifications.\n
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\n \n\n \n \n \n \n \n \n Effects of a halogenated G-quadruplex ligand from the pyridine dicarboxamide series on the terminal sequence of XpYp telomere in HT1080 cells.\n \n \n \n \n\n\n \n Sidibe, A.; Hamon, F.; Largy, E.; Gomez, D.; Teulade-Fichou, M.; Trentesaux, C.; and Riou, J.\n\n\n \n\n\n\n Biochimie, 94(12): 1–10. July 2012.\n \n\n\n\n
\n\n\n\n \n \n \"EffectsPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
\n 
@article{Sidibe2012,\n\ttitle = {Effects of a halogenated {G}-quadruplex ligand from the pyridine dicarboxamide series on the terminal sequence of {XpYp} telomere in {HT1080} cells.},\n\tvolume = {94},\n\tcopyright = {All rights reserved},\n\tissn = {1638-6183},\n\turl = {http://www.ncbi.nlm.nih.gov/pubmed/22796264},\n\tdoi = {10.1016/j.biochi.2012.07.003},\n\tabstract = {Non-canonical four-stranded structures called G-quadruplexes can form among telomere repeats during its replication. Small molecule ligands able to interact and to stabilize G-quadruplexes were shown to disrupt the binding of essential telomeric components, such as POT1 and to trigger a telomeric dysfunction associated with a delayed growth arrest in tumor cells. We describe here the chemical synthesis and the G-quadruplex binding properties of three halogenated analogs of the 360A ligand that belongs to the 2,6 pyridine dicarboxamide series. 360A is now commonly used as a benchmark both for biophysical and cellular assays as this compound was shown to display a potent affinity and selectivity for telomeric G-quadruplex DNA over duplex DNA and to induce delayed growth inhibition in HT1080 tumor cell line. Two biophysical assays indicate that, in most cases, the presence of the halogen atom seems to slightly improve the interaction with the telomeric quadruplex. For stability reasons, the bromo derivative (360A-Br) was selected for the cellular assays. Since POT1 participates to the fine tuning of the C-strand end resection during telomere replication, we investigated the effect of 360A-Br to alter the terminal nucleotide composition of XpYp telomere in HT1080 cells using C-STELA. HT1080 cells treated for up to 24 days with 360A-Br presented some minor but significant variations of C-strand terminal nucleotide composition, also observed with a partial siRNA depletion of POT1. The relevance of these minor modifications of the telomeric C-strand resection induced by 360A-Br in HT1080 cells are discussed.},\n\tnumber = {12},\n\tjournal = {Biochimie},\n\tauthor = {Sidibe, Assitan and Hamon, Florian and Largy, Eric and Gomez, Dennis and Teulade-Fichou, Marie-Paule and Trentesaux, Chantal and Riou, Jean-François},\n\tmonth = jul,\n\tyear = {2012},\n\tpmid = {22796264},\n\tpages = {1--10},\n}\n\n
\n
\n\n\n
\n Non-canonical four-stranded structures called G-quadruplexes can form among telomere repeats during its replication. Small molecule ligands able to interact and to stabilize G-quadruplexes were shown to disrupt the binding of essential telomeric components, such as POT1 and to trigger a telomeric dysfunction associated with a delayed growth arrest in tumor cells. We describe here the chemical synthesis and the G-quadruplex binding properties of three halogenated analogs of the 360A ligand that belongs to the 2,6 pyridine dicarboxamide series. 360A is now commonly used as a benchmark both for biophysical and cellular assays as this compound was shown to display a potent affinity and selectivity for telomeric G-quadruplex DNA over duplex DNA and to induce delayed growth inhibition in HT1080 tumor cell line. Two biophysical assays indicate that, in most cases, the presence of the halogen atom seems to slightly improve the interaction with the telomeric quadruplex. For stability reasons, the bromo derivative (360A-Br) was selected for the cellular assays. Since POT1 participates to the fine tuning of the C-strand end resection during telomere replication, we investigated the effect of 360A-Br to alter the terminal nucleotide composition of XpYp telomere in HT1080 cells using C-STELA. HT1080 cells treated for up to 24 days with 360A-Br presented some minor but significant variations of C-strand terminal nucleotide composition, also observed with a partial siRNA depletion of POT1. The relevance of these minor modifications of the telomeric C-strand resection induced by 360A-Br in HT1080 cells are discussed.\n
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\n  \n 2011\n \n \n (7)\n \n \n
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\n \n\n \n \n \n \n \n \n An acyclic oligoheteroaryle that discriminates strongly between diverse g-quadruplex topologies.\n \n \n \n \n\n\n \n Hamon, F.; Largy, E.; Guédin-Beaurepaire, A.; Rouchon-Dagois, M.; Sidibe, A.; Monchaud, D.; Mergny, J.; Riou, J.; Nguyen, C.; and Teulade-Fichou, M.\n\n\n \n\n\n\n Angewandte Chemie (International ed. in English), 50(37): 8745–8749. August 2011.\n publisher: Wiley Online Library\n\n\n\n
\n\n\n\n \n \n \"AnPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n\n\n\n
\n 
@article{Hamon2011,\n\ttitle = {An acyclic oligoheteroaryle that discriminates strongly between diverse g-quadruplex topologies.},\n\tvolume = {50},\n\tcopyright = {All rights reserved},\n\tissn = {1521-3773},\n\turl = {http://www.ncbi.nlm.nih.gov/pubmed/21812083},\n\tdoi = {10.1002/anie.201103422},\n\tnumber = {37},\n\tjournal = {Angewandte Chemie (International ed. in English)},\n\tauthor = {Hamon, Florian and Largy, Eric and Guédin-Beaurepaire, Aurore and Rouchon-Dagois, Myriam and Sidibe, Assitan and Monchaud, David and Mergny, Jean-Louis and Riou, Jean-Francois and Nguyen, Chi-Hung and Teulade-Fichou, Marie-Paule},\n\tmonth = aug,\n\tyear = {2011},\n\tpmid = {21812083},\n\tnote = {publisher: Wiley Online Library},\n\tkeywords = {DNA, DNA: chemistry, DNA: drug effects, G-Quadruplexes, G-Quadruplexes: drug effects, Molecular Structure, Oxazoles, Oxazoles: chemical synthesis, Oxazoles: chemistry, Oxazoles: pharmacology, Structure-Activity Relationship},\n\tpages = {8745--8749},\n}\n\n
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\n \n\n \n \n \n \n \n \n Nucleic acids targeted to drugs: SELEX against a quadruplex ligand.\n \n \n \n \n\n\n \n Renaud de la Faverie, A.; Hamon, F.; Primo, C. D.; Largy, E.; Dausse, E.; Delaurière, L.; Landras-Guetta, C.; Toulmé, J.; Teulade-Fichou, M.; and Mergny, J.\n\n\n \n\n\n\n Biochimie, 93(8): 1357–1367. August 2011.\n publisher: Elsevier Masson SAS\n\n\n\n
\n\n\n\n \n \n \"NucleicPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n\n\n\n
\n 
@article{renaud_de_la_faverie_nucleic_2011,\n\ttitle = {Nucleic acids targeted to drugs: {SELEX} against a quadruplex ligand},\n\tvolume = {93},\n\tcopyright = {All rights reserved},\n\tissn = {03009084},\n\turl = {http://dx.doi.org/10.1016/j.biochi.2011.05.022 http://linkinghub.elsevier.com/retrieve/pii/S0300908411001799},\n\tdoi = {10.1016/j.biochi.2011.05.022},\n\tnumber = {8},\n\tjournal = {Biochimie},\n\tauthor = {Renaud de la Faverie, Amandine and Hamon, Florian and Primo, Carmelo Di and Largy, Eric and Dausse, Eric and Delaurière, Laurence and Landras-Guetta, Corinne and Toulmé, Jean-jacques and Teulade-Fichou, Marie-Paule and Mergny, Jean-louis},\n\tmonth = aug,\n\tyear = {2011},\n\tpmid = {21664224},\n\tnote = {publisher: Elsevier Masson SAS},\n\tpages = {1357--1367},\n}\n\n
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\n \n\n \n \n \n \n \n \n Development of a high-throughput G4-FID assay for screening and evaluation of small molecules binding quadruplex nucleic acid structures.\n \n \n \n \n\n\n \n Largy, E.; Hamon, F.; and Teulade-Fichou, M.\n\n\n \n\n\n\n Analytical and Bioanalytical Chemistry, 400(10): 3419–3427. July 2011.\n \n\n\n\n
\n\n\n\n \n \n \"DevelopmentPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n\n\n\n
\n 
@article{Largy2011,\n\ttitle = {Development of a high-throughput {G4}-{FID} assay for screening and evaluation of small molecules binding quadruplex nucleic acid structures},\n\tvolume = {400},\n\tcopyright = {All rights reserved},\n\tissn = {1618-2642},\n\turl = {http://www.ncbi.nlm.nih.gov/pubmed/21528379 http://dx.doi.org/10.1007/s00216-011-5018-z http://link.springer.com/10.1007/s00216-011-5018-z},\n\tdoi = {10.1007/s00216-011-5018-z},\n\tabstract = {G4-FID (G-quadruplex fluorescent intercalator displacement) is a simple and fast method that allows to evaluate the affinity of a compound for G-quadruplex DNA and its selectivity towards duplex DNA. This assay is based on the loss of fluorescence of thiazole orange (TO) upon competitive displacement from DNA by a putative ligand. We describe here the development of a high-throughput version of this assay performed in 96-well microplates, and fully transposable to 384-well microplates. The test was calibrated with a set of G-quadruplex ligands characterized for their ability to bind quadruplex within a large range of affinity. The comparison of the results obtained in microplates and in cuvettes was conducted indicating a full agreement. Additionally, the spectral range of the test was enlarged using two other fluorescent on/off probes whose absorption are red-shifted (TO-PRO-3) and blue-shifted (Hoechst 33258) as compared to that of TO. These labels enable to screen a large diversity of compounds with various optical properties, which was exemplified by evaluation of affinity and selectivity of the porphyrin TMPyP4 that could not be evaluated previously. Altogether, our study demonstrates that the HT-G4-FID assay offers the possibility to label a large variety of G-quadruplexes of biological interest and should enable screening of collections of putative G4-ligands of high structural diversity. It thus represents a powerful tool to bring into light new ligands able to discriminate between quadruplexes of different structures. Figure High-throughput screening and evaluation of quadruplex nucleic acid ligands},\n\tnumber = {10},\n\tjournal = {Analytical and Bioanalytical Chemistry},\n\tauthor = {Largy, Eric and Hamon, Florian and Teulade-Fichou, Marie-Paule},\n\tmonth = jul,\n\tyear = {2011},\n\tpmid = {21528379},\n\tkeywords = {Benzothiazoles, Engineering, Fluorescent Dyes, G-Quadruplexes, High-Throughput Screening Assays, High-Throughput Screening Assays: methods, Ligands, Quinolines},\n\tpages = {3419--3427},\n}\n\n
\n
\n\n\n
\n G4-FID (G-quadruplex fluorescent intercalator displacement) is a simple and fast method that allows to evaluate the affinity of a compound for G-quadruplex DNA and its selectivity towards duplex DNA. This assay is based on the loss of fluorescence of thiazole orange (TO) upon competitive displacement from DNA by a putative ligand. We describe here the development of a high-throughput version of this assay performed in 96-well microplates, and fully transposable to 384-well microplates. The test was calibrated with a set of G-quadruplex ligands characterized for their ability to bind quadruplex within a large range of affinity. The comparison of the results obtained in microplates and in cuvettes was conducted indicating a full agreement. Additionally, the spectral range of the test was enlarged using two other fluorescent on/off probes whose absorption are red-shifted (TO-PRO-3) and blue-shifted (Hoechst 33258) as compared to that of TO. These labels enable to screen a large diversity of compounds with various optical properties, which was exemplified by evaluation of affinity and selectivity of the porphyrin TMPyP4 that could not be evaluated previously. Altogether, our study demonstrates that the HT-G4-FID assay offers the possibility to label a large variety of G-quadruplexes of biological interest and should enable screening of collections of putative G4-ligands of high structural diversity. It thus represents a powerful tool to bring into light new ligands able to discriminate between quadruplexes of different structures. Figure High-throughput screening and evaluation of quadruplex nucleic acid ligands\n
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\n \n\n \n \n \n \n \n \n Tridentate n-donor Palladium(II) complexes as efficient coordinating quadruplex DNA binders.\n \n \n \n \n\n\n \n Largy, E.; Hamon, F.; Rosu, F.; Gabelica, V.; Pauw, E. D.; Guédin, A.; Mergny, J.; and Teulade-Fichou, M.\n\n\n \n\n\n\n Chemistry - A European Journal, 17(47): 13274–13283. November 2011.\n \n\n\n\n
\n\n\n\n \n \n \"TridentatePaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n\n\n\n
\n 
@article{Largy2011,\n\ttitle = {Tridentate n-donor {Palladium}({II}) complexes as efficient coordinating quadruplex {DNA} binders},\n\tvolume = {17},\n\tcopyright = {All rights reserved},\n\tissn = {09476539},\n\turl = {http://www.ncbi.nlm.nih.gov/pubmed/22006796 http://doi.wiley.com/10.1002/chem.201102300},\n\tdoi = {10.1002/chem.201102300},\n\tabstract = {Fifteen complexes of palladium, platinum, and copper, featuring five different N-donor tridentate (terpyridine-like) ligands, were prepared with the aim of testing their G-quadruplex-DNA binding properties. The fluorescence resonance energy transfer melting assay indicated a striking positive effect of palladium on G-quadruplex DNA stabilization compared with platinum and copper, as well as an influence of the structure of the organic ligand. Putative binding modes (noncoordinative π stacking and base coordination) of palladium and platinum complexes were investigated by ESI-MS and UV/Vis spectroscopy experiments, which all revealed a greater ability of palladium complexes to coordinate DNA bases. In contrast, platinum compounds tend to predominantly bind to quadruplex DNA in their aqua form by noncoordinative interactions. Remarkably, complexes of Pd(ttpy) and Pd(tMebip) (ttpy=tolylterpyridine, tMebip=2,2'-(4-p-tolylpyridine-2,6-diyl)bis(1-methyl-1H-benzodimidazole)) coordinate efficiently G-quadruplex structures at room temperature in less than 1h, and are more efficient than their platinum counterparts for inhibiting the growth of cancer cells. Altogether, these results demonstrate that both the affinity for G-quadruplex DNA and the binding mode of metal complexes can be modulated by modifying either the metal or the organic ligand.},\n\tnumber = {47},\n\tjournal = {Chemistry - A European Journal},\n\tauthor = {Largy, Eric and Hamon, Florian and Rosu, Frédéric and Gabelica, Valérie and Pauw, Edwin De and Guédin, Aurore and Mergny, Jean-Louis and Teulade-Fichou, Marie-Paule},\n\tmonth = nov,\n\tyear = {2011},\n\tpmid = {22006796},\n\tkeywords = {dna, fret, g quad, mass spectrometry, ruplexes, tran},\n\tpages = {13274--13283},\n}\n\n
\n
\n\n\n
\n Fifteen complexes of palladium, platinum, and copper, featuring five different N-donor tridentate (terpyridine-like) ligands, were prepared with the aim of testing their G-quadruplex-DNA binding properties. The fluorescence resonance energy transfer melting assay indicated a striking positive effect of palladium on G-quadruplex DNA stabilization compared with platinum and copper, as well as an influence of the structure of the organic ligand. Putative binding modes (noncoordinative π stacking and base coordination) of palladium and platinum complexes were investigated by ESI-MS and UV/Vis spectroscopy experiments, which all revealed a greater ability of palladium complexes to coordinate DNA bases. In contrast, platinum compounds tend to predominantly bind to quadruplex DNA in their aqua form by noncoordinative interactions. Remarkably, complexes of Pd(ttpy) and Pd(tMebip) (ttpy=tolylterpyridine, tMebip=2,2'-(4-p-tolylpyridine-2,6-diyl)bis(1-methyl-1H-benzodimidazole)) coordinate efficiently G-quadruplex structures at room temperature in less than 1h, and are more efficient than their platinum counterparts for inhibiting the growth of cancer cells. Altogether, these results demonstrate that both the affinity for G-quadruplex DNA and the binding mode of metal complexes can be modulated by modifying either the metal or the organic ligand.\n
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\n \n\n \n \n \n \n \n Fluorescence intercalator displacement assay for screening G4 ligands towards a variety of G-quadruplex structures.\n \n \n \n\n\n \n Tran, P L; Largy, E.; Hamon, F.; Teulade-Fichou, M.; and Mergny, J.\n\n\n \n\n\n\n Biochimie, 93(8): 1288–1296. 2011.\n publisher: Elsevier Masson SAS\n\n\n\n
\n\n\n\n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n\n\n\n
\n 
@article{Tran2011,\n\ttitle = {Fluorescence intercalator displacement assay for screening {G4} ligands towards a variety of {G}-quadruplex structures.},\n\tvolume = {93},\n\tcopyright = {All rights reserved},\n\tdoi = {10.1016/j.biochi.2011.05.011},\n\tnumber = {8},\n\tjournal = {Biochimie},\n\tauthor = {Tran, P L and Largy, Eric and Hamon, Florian and Teulade-Fichou, Marie-Paule and Mergny, Jean-Louis},\n\tyear = {2011},\n\tpmid = {21641961},\n\tnote = {publisher: Elsevier Masson SAS},\n\tkeywords = {Benzothiazoles, Benzothiazoles: chemistry, Circular Dichroism, Drug Evaluation, Fluorescence, Fluorescent Dyes, Fluorescent Dyes: chemistry, G-Quadruplexes, High-Throughput Screening Assays, Intercalating Agents, Intercalating Agents: chemistry, Ligands, Preclinical, Preclinical: methods, Quadruplex DNA-DNA ligand interactions Fluorescenc, Quinolines, Quinolines: chemistry},\n\tpages = {1288--1296},\n}\n\n
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\n \n\n \n \n \n \n \n \n Ciblage d’Acides nucléiques g-quadruplexes : Synthèse et développement de méthode pour l’Analyse et le criblage de ligands sélectifs multimodaux.\n \n \n \n \n\n\n \n Largy, E.\n\n\n \n\n\n\n Ph.D. Thesis, Paris 11 / Université Paris XI, 2011.\n Pages: 252\n\n\n\n
\n\n\n\n \n \n \"CiblagePaper\n  \n \n\n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n\n\n\n
\n 
@phdthesis{Largy2011,\n\ttitle = {Ciblage d’{Acides} nucléiques g-quadruplexes : {Synthèse} et développement de méthode pour l’{Analyse} et le criblage de ligands sélectifs multimodaux},\n\tcopyright = {All rights reserved},\n\turl = {http://www.theses.fr/2011PA112257},\n\tabstract = {The aim of this thesis work was to study the interactions of small molecules with multiple structures of quadruplex DNA via i) the development and use of a high-throughput test for the analysis of ligand-quadruplex DNA interactions and screening of chemical libraries and ii) the preparation of compounds with multiple binding modes (stacking/groove, covalent/non-covalent, etc..) selective (quadruplex vs. duplex and intra-quadruplex) and possibly functionalized (biotin, fluorophore, etc.). The first part of the work was focused on the development of the G4-FID (G-quadruplex Intercalator Fluorescent Displacement) assay, which is a semi-quantitative method for evaluating the affinity and selectivity of small molecules for quadruplex DNA by displacing an off/on probe, the Thiazole Orange (TO). The test has been implemented successfully with microplate (HT-G4-FID). On the other hand, we have shown the importance of alternative fluorophores, TO-PRO-3 and Hoechst 33258, with complementary spectral characteristics. This method of analysis has also been successfully used for the identification of new selective ligands of quadruplex DNA and the identification of structure-activity relationships and structural selectivities. The second part of the work was devoted to the preparation and study of new DNA quadruplex ligands. These ligands possess particular characteristics either in their mode of interaction (grooves, coordination) or by their bifunctionality (biotinylated, fluorescent). We have prepared an acyclic polyheteroaryle quadruplex ligand (TOxaPy) with an unexpected selectivity for certain structures of quadruplex DNA. Furthermore, we showed that complexes of terpyridine derivatives can be tailored by changing the organic ligand and / or the metal in order to interact with quadruplex DNA by covalent and / or non-covalent interaction.},\n\tschool = {Paris 11 / Université Paris XI},\n\tauthor = {Largy, Eric},\n\tyear = {2011},\n\tnote = {Pages: 252},\n\tkeywords = {\\#nosource},\n}\n\n
\n
\n\n\n
\n The aim of this thesis work was to study the interactions of small molecules with multiple structures of quadruplex DNA via i) the development and use of a high-throughput test for the analysis of ligand-quadruplex DNA interactions and screening of chemical libraries and ii) the preparation of compounds with multiple binding modes (stacking/groove, covalent/non-covalent, etc..) selective (quadruplex vs. duplex and intra-quadruplex) and possibly functionalized (biotin, fluorophore, etc.). The first part of the work was focused on the development of the G4-FID (G-quadruplex Intercalator Fluorescent Displacement) assay, which is a semi-quantitative method for evaluating the affinity and selectivity of small molecules for quadruplex DNA by displacing an off/on probe, the Thiazole Orange (TO). The test has been implemented successfully with microplate (HT-G4-FID). On the other hand, we have shown the importance of alternative fluorophores, TO-PRO-3 and Hoechst 33258, with complementary spectral characteristics. This method of analysis has also been successfully used for the identification of new selective ligands of quadruplex DNA and the identification of structure-activity relationships and structural selectivities. The second part of the work was devoted to the preparation and study of new DNA quadruplex ligands. These ligands possess particular characteristics either in their mode of interaction (grooves, coordination) or by their bifunctionality (biotinylated, fluorescent). We have prepared an acyclic polyheteroaryle quadruplex ligand (TOxaPy) with an unexpected selectivity for certain structures of quadruplex DNA. Furthermore, we showed that complexes of terpyridine derivatives can be tailored by changing the organic ligand and / or the metal in order to interact with quadruplex DNA by covalent and / or non-covalent interaction.\n
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\n \n\n \n \n \n \n \n Recognition of DNA secondary structures: From structure to fluorescent probes.\n \n \n \n\n\n \n Granzhan, A.; Saettel, N.; Hamon, F.; Largy, E.; Guetta, C.; and Teulade-Fichou, M.\n\n\n \n\n\n\n In of Chemistry of Nucleic Acid Components - Collection symposium series, 2011. \n \n\n\n\n
\n\n\n\n \n\n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n\n\n\n
\n 
@inproceedings{Granzhan2011,\n\tseries = {Chemistry of {Nucleic} {Acid} {Components} - {Collection} symposium series},\n\ttitle = {Recognition of {DNA} secondary structures: {From} structure to fluorescent probes},\n\tcopyright = {All rights reserved},\n\tabstract = {DNA can exist in a variety of secondary structures that have profound effects on several biological processes such as gene regulation and disease. Targeting DNA secondary structures by small molecules is challenging but holds a great potential for future therapeutic and biochemical applications. Herein we give examples of diverse chemical scaffolds and strategies developed for targeting mismatched DNA and G-quadruplexes.},\n\tauthor = {Granzhan, Anton and Saettel, Nicolas and Hamon, Florian and Largy, Eric and Guetta, Corinne and Teulade-Fichou, Marie-Paule},\n\tyear = {2011},\n\tkeywords = {\\#nosource, ⛔ No DOI found},\n}\n
\n
\n\n\n
\n DNA can exist in a variety of secondary structures that have profound effects on several biological processes such as gene regulation and disease. Targeting DNA secondary structures by small molecules is challenging but holds a great potential for future therapeutic and biochemical applications. Herein we give examples of diverse chemical scaffolds and strategies developed for targeting mismatched DNA and G-quadruplexes.\n
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\n  \n 2010\n \n \n (3)\n \n \n
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\n \n\n \n \n \n \n \n Macrocyclic DNA-mismatch-binding ligands: Structural determinants of selectivity.\n \n \n \n\n\n \n Granzhan, A.; Largy, E.; Saettel, N.; and Teulade-Fichou, M.\n\n\n \n\n\n\n Chemistry - A European Journal, 16(3): 878–889. 2010.\n publisher: Wiley Online Library\n\n\n\n
\n\n\n\n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n\n\n\n
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@article{Granzhan2010,\n\ttitle = {Macrocyclic {DNA}-mismatch-binding ligands: {Structural} determinants of selectivity},\n\tvolume = {16},\n\tcopyright = {All rights reserved},\n\tissn = {09476539 15213765},\n\tdoi = {10.1002/chem.200901989},\n\tabstract = {A collection of 15 homodi- meric and 5 heterodimeric macrocyclic bisintercalators was prepared by one- or two-step condensation of aromatic dialdehydes with aliphatic diamines; notably, the heterodimeric scaffolds were synthesized for the first time. The binding of these macrocycles to DNA duplexes containing a mispaired thy- mine residue (TX), as well as to the fully paired control (TA), was investi- gated by thermal denaturation and flu- orescent-intercalator-displacement experiments. The bisnaphthalene derivatives, in particular, the 2, 7-disubstituted ones, have the highest selectivity for the TX mismatches, as these macrocy- cles show no apparent binding to the fully paired DNA. By contrast, other macrocyclic ligands, as well as seven conventional DNA binders, show lesser or no selectivity for the mismatch sites. The study demonstrates that the topology of the ligands plays a crucial role in determining the mismatch-binding affinity and selectivity of the macrocy- clic bisintercalators. ©2010 Wiley-VCH Verlag GmbH \\& Co. KGaA.},\n\tnumber = {3},\n\tjournal = {Chemistry - A European Journal},\n\tauthor = {Granzhan, A. and Largy, E. and Saettel, N. and Teulade-Fichou, M.-P.},\n\tyear = {2010},\n\tpmid = {19938008},\n\tnote = {publisher: Wiley Online Library},\n\tkeywords = {Aldehydes: chemistry, Bisintercalators, DNA mismatches, DNA recognition, DNA: chemistry, Diamines: chemistry, Fluorescent Dyes: chemistry, Intercalating Agents: chemical synthesis, Intercalating Agents: chemistry, Intercalations, Macrocycles, Macrocyclic Compounds: chemical synthesis, Macrocyclic Compounds: chemistry, Naphthalenes: chemistry, aldehydes, aldehydes chemistry, base pair mismatch, bisintercalators, diamines, diamines chemistry, dna, dna chemistry, dna mismatches, dna recogni-, fluorescent dyes, fluorescent dyes chemistry, intercalating agents, intercalating agents chemical synthesis, intercalating agents chemistry, intercalations, ligands, macrocyclic compounds, macrocyclic compounds chemical synthesis, macrocyclic compounds chemistry, naphthalenes, naphthalenes chemistry, transition temperature},\n\tpages = {878--889},\n}\n\n
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\n A collection of 15 homodi- meric and 5 heterodimeric macrocyclic bisintercalators was prepared by one- or two-step condensation of aromatic dialdehydes with aliphatic diamines; notably, the heterodimeric scaffolds were synthesized for the first time. The binding of these macrocycles to DNA duplexes containing a mispaired thy- mine residue (TX), as well as to the fully paired control (TA), was investi- gated by thermal denaturation and flu- orescent-intercalator-displacement experiments. The bisnaphthalene derivatives, in particular, the 2, 7-disubstituted ones, have the highest selectivity for the TX mismatches, as these macrocy- cles show no apparent binding to the fully paired DNA. By contrast, other macrocyclic ligands, as well as seven conventional DNA binders, show lesser or no selectivity for the mismatch sites. The study demonstrates that the topology of the ligands plays a crucial role in determining the mismatch-binding affinity and selectivity of the macrocy- clic bisintercalators. ©2010 Wiley-VCH Verlag GmbH & Co. KGaA.\n
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\n \n\n \n \n \n \n \n \n Genetic instability triggered by G-quadruplex interacting Phen-DC compounds in Saccharomyces cerevisiae.\n \n \n \n \n\n\n \n Piazza, A. A.; Boule, J.; Lopes, J.; Mingo, K.; Largy, E.; Teulade-Fichou, M.; Nicolas, A.; and Boulé, J.\n\n\n \n\n\n\n Nucleic Acids Research, 38(13): 4337–4348. July 2010.\n publisher: Oxford Univ Press\n\n\n\n
\n\n\n\n \n \n \"GeneticPaper\n  \n \n\n \n \n doi\n  \n \n\n \n link\n  \n \n\n bibtex\n \n\n \n  \n \n abstract \n \n\n \n\n \n \n \n \n \n \n \n\n  \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n \n\n\n\n
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@article{Piazza2010,\n\ttitle = {Genetic instability triggered by {G}-quadruplex interacting {Phen}-{DC} compounds in {Saccharomyces} cerevisiae},\n\tvolume = {38},\n\tcopyright = {All rights reserved},\n\tissn = {1362-4962},\n\turl = {http://nar.oxfordjournals.org/cgi/content/abstract/38/13/4337 http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=2910037&tool=pmcentrez&rendertype=abstract},\n\tdoi = {10.1093/nar/gkq136},\n\tabstract = {G-quadruplexes are nucleic acid secondary structures for which many biological roles have been proposed but whose existence in vivo has remained elusive. To assess their formation, highly specific G-quadruplex ligands are needed. Here, we tested Phen-DC3 and Phen-DC6, two recently released ligands of the bisquinolinium class. In vitro, both compounds exhibit high affinity for the G4 formed by the human minisatellite CEB1 and inhibit efficiently their unwinding by the yeast Pif1 helicase. In vivo, both compounds rapidly induced recombination-dependent rearrangements of CEB1 inserted in the Saccharomyces cerevisiae genome, but did not affect the stability of other tandem repeats lacking G-quadruplex forming sequences. The rearrangements yielded simple-deletion, double-deletion or complex reshuffling of the polymorphic motif units, mimicking the phenotype of the Pif1 inactivation. Treatment of Pif1-deficient cells with the Phen-DC compounds further increased CEB1 instability, revealing additional G4 formation per cell. In sharp contrast, the commonly used N-methyl-mesoporphyrin IX G-quadruplex ligand did not affect CEB1 stability. Altogether, these results demonstrate that the Phen-DC bisquinolinium compounds are potent molecular tools for probing the formation of G-quadruplexes in vivo, interfere with their processing and elucidate their biological roles.},\n\tnumber = {13},\n\tjournal = {Nucleic Acids Research},\n\tauthor = {Piazza, Aurèle Aurele and Boule, Jean-Baptiste and Lopes, Judith and Mingo, Katie and Largy, Eric and Teulade-Fichou, Marie-Paule and Nicolas, Alain and Boulé, Jean-Baptiste},\n\tmonth = jul,\n\tyear = {2010},\n\tpmid = {20223771},\n\tnote = {publisher: Oxford Univ Press},\n\tkeywords = {DNA Helicases, DNA Helicases: genetics, DNA Helicases: metabolism, G-Quadruplexes, G-Quadruplexes: drug effects, Genetic, Genetic Variation, Humans, Ligands, Minisatellite Repeats, Minisatellite Repeats: drug effects, Mutation, Phenanthrolines, Phenanthrolines: chemistry, Phenanthrolines: metabolism, Phenanthrolines: pharmacology, Quinolinium Compounds, Quinolinium Compounds: chemistry, Quinolinium Compounds: metabolism, Quinolinium Compounds: pharmacology, Recombination, Saccharomyces cerevisiae, Saccharomyces cerevisiae Proteins, Saccharomyces cerevisiae Proteins: genetics, Saccharomyces cerevisiae Proteins: metabolism, Saccharomyces cerevisiae: drug effects, Saccharomyces cerevisiae: genetics},\n\tpages = {4337--4348},\n}\n\n
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\n G-quadruplexes are nucleic acid secondary structures for which many biological roles have been proposed but whose existence in vivo has remained elusive. To assess their formation, highly specific G-quadruplex ligands are needed. Here, we tested Phen-DC3 and Phen-DC6, two recently released ligands of the bisquinolinium class. In vitro, both compounds exhibit high affinity for the G4 formed by the human minisatellite CEB1 and inhibit efficiently their unwinding by the yeast Pif1 helicase. In vivo, both compounds rapidly induced recombination-dependent rearrangements of CEB1 inserted in the Saccharomyces cerevisiae genome, but did not affect the stability of other tandem repeats lacking G-quadruplex forming sequences. The rearrangements yielded simple-deletion, double-deletion or complex reshuffling of the polymorphic motif units, mimicking the phenotype of the Pif1 inactivation. Treatment of Pif1-deficient cells with the Phen-DC compounds further increased CEB1 instability, revealing additional G4 formation per cell. In sharp contrast, the commonly used N-methyl-mesoporphyrin IX G-quadruplex ligand did not affect CEB1 stability. Altogether, these results demonstrate that the Phen-DC bisquinolinium compounds are potent molecular tools for probing the formation of G-quadruplexes in vivo, interfere with their processing and elucidate their biological roles.\n
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\n \n\n \n \n \n \n \n High affinity G-quadruplex binders Phen-DC compounds trigger genetic instability in yeast.\n \n \n \n\n\n \n Boule, J B; Lacroix, L; Largy, E; Lopez, J; Mingo, K; Nicolas, A; Piazza, A; and Tuelade-Fichou, M\n\n\n \n\n\n\n In 2010. \n \n\n\n\n
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@inproceedings{Boule2010,\n\ttitle = {High affinity {G}-quadruplex binders {Phen}-{DC} compounds trigger genetic instability in yeast},\n\tcopyright = {All rights reserved},\n\tauthor = {Boule, J B and Lacroix, L and Largy, E and Lopez, J and Mingo, K and Nicolas, A and Piazza, A and Tuelade-Fichou, M},\n\tyear = {2010},\n\tkeywords = {\\#nosource, ⛔ No DOI found},\n}\n\n
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