Asymmetric distyrylpyridinium dyes as red-emitting fluorescent probes for quadruplex DNA. Xie, X., Choi, B., Largy, E., Guillot, R., Granzhan, A., & Teulade-Fichou, M. Chemistry - A European Journal, 19:1214–1226, 2013. doi abstract bibtex 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.
@article{xie_asymmetric_2013,
title = {Asymmetric distyrylpyridinium dyes as red-emitting fluorescent probes for quadruplex {DNA}.},
volume = {19},
copyright = {All rights reserved},
doi = {10.1002/chem.201203710},
abstract = {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.},
journal = {Chemistry - A European Journal},
author = {Xie, Xiao and Choi, Bina and Largy, Eric and Guillot, Régis and Granzhan, Anton and Teulade-Fichou, Marie-Paule},
year = {2013},
pmid = {23292703},
keywords = {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},
pages = {1214--1226},
}
Downloads: 0
{"_id":"8R5y2BtQwcdZtxmdQ","bibbaseid":"xie-choi-largy-guillot-granzhan-teuladefichou-asymmetricdistyrylpyridiniumdyesasredemittingfluorescentprobesforquadruplexdna-2013","author_short":["Xie, X.","Choi, B.","Largy, E.","Guillot, R.","Granzhan, A.","Teulade-Fichou, M."],"bibdata":{"bibtype":"article","type":"article","title":"Asymmetric distyrylpyridinium dyes as red-emitting fluorescent probes for quadruplex DNA.","volume":"19","copyright":"All rights reserved","doi":"10.1002/chem.201203710","abstract":"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.","journal":"Chemistry - A European Journal","author":[{"propositions":[],"lastnames":["Xie"],"firstnames":["Xiao"],"suffixes":[]},{"propositions":[],"lastnames":["Choi"],"firstnames":["Bina"],"suffixes":[]},{"propositions":[],"lastnames":["Largy"],"firstnames":["Eric"],"suffixes":[]},{"propositions":[],"lastnames":["Guillot"],"firstnames":["Régis"],"suffixes":[]},{"propositions":[],"lastnames":["Granzhan"],"firstnames":["Anton"],"suffixes":[]},{"propositions":[],"lastnames":["Teulade-Fichou"],"firstnames":["Marie-Paule"],"suffixes":[]}],"year":"2013","pmid":"23292703","keywords":"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","pages":"1214–1226","bibtex":"@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","author_short":["Xie, X.","Choi, B.","Largy, E.","Guillot, R.","Granzhan, A.","Teulade-Fichou, M."],"key":"xie_asymmetric_2013","id":"xie_asymmetric_2013","bibbaseid":"xie-choi-largy-guillot-granzhan-teuladefichou-asymmetricdistyrylpyridiniumdyesasredemittingfluorescentprobesforquadruplexdna-2013","role":"author","urls":{},"keyword":["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"],"metadata":{"authorlinks":{}}},"bibtype":"article","biburl":"https://api.zotero.org/users/7089346/collections/W8METNZK/items?key=DFVpFyHB0pzrEBQ8agtoT8MF&format=bibtex&limit=100","dataSources":["2R7MLTLo2etR9L3gc","mNu69AQZeirb46MYR","u78Bhos3FtTwmkpiP","LNNihAsamhTzAbFhz","cwLNp2H3oNkmE4Hxd","4i5C7S78DvJNsaHyg","mQ655wYbmBY87sBpa","5L2zM5wNE5CBYNuea","gtEmYbDwieyT97hcW"],"keywords":["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"],"search_terms":["asymmetric","distyrylpyridinium","dyes","red","emitting","fluorescent","probes","quadruplex","dna","xie","choi","largy","guillot","granzhan","teulade-fichou"],"title":"Asymmetric distyrylpyridinium dyes as red-emitting fluorescent probes for quadruplex DNA.","year":2013}