Macrocyclic DNA-mismatch-binding ligands: Structural determinants of selectivity. Granzhan, A., Largy, E., Saettel, N., & Teulade-Fichou, M. Chemistry - A European Journal, 16(3):878–889, Wiley Online Library, 2010. doi abstract bibtex 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.
@article{granzhanMacrocyclicDNAmismatchbindingLigands2010b,
title = {Macrocyclic {DNA}-mismatch-binding ligands: {Structural} determinants of selectivity},
volume = {16},
copyright = {All rights reserved},
issn = {09476539 15213765},
doi = {10.1002/chem.200901989},
abstract = {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.},
number = {3},
journal = {Chemistry - A European Journal},
publisher = {Wiley Online Library},
author = {Granzhan, A. and Largy, E. and Saettel, N. and Teulade-Fichou, M.-P.},
year = {2010},
keywords = {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},
pages = {878--889},
}
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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. 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