Macrocyclic DNA-mismatch-binding ligands: structural determinants of selectivity

Chemistry : a European Journal
Anton GranzhanMarie-Paule Teulade-Fichou

Abstract

A collection of 15 homodimeric 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 thymine residue (TX), as well as to the fully paired control (TA), was investigated by thermal denaturation and fluorescent-intercalator-displacement experiments. The bisnaphthalene derivatives, in particular, the 2,7-disubstituted ones, have the highest selectivity for the TX mismatches, as these macrocycles 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 macrocyclic bisintercalators.

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Citations

Aug 21, 2010·Journal of Nucleic Acids·David MonchaudMarie-Paule Teulade-Fichou
Feb 11, 2015·International Journal of Molecular Sciences·Delphine PaolantoniSébastien Ulrich
Nov 18, 2015·ACS Chemical Biology·Scott E AllenAlbert A Bowers
Dec 11, 2013·Biotechnology Journal·Delphine Naud-MartinMarie-Paule Teulade-Fichou
Mar 19, 2014·Chemical Society Reviews·Anton GranzhanMarie-Paule Teulade-Fichou
Jan 21, 2017·Chembiochem : a European Journal of Chemical Biology·Naoko KoteraAnton Granzhan
Nov 18, 2017·Nucleic Acids Research·Ludivine GuyonDavid Monchaud
Aug 22, 2014·Nucleic Acids Research·Eric Largy, Jean-Louis Mergny
Nov 5, 2014·Organic & Biomolecular Chemistry·Jana NovotnaDavid Monchaud
Sep 18, 2015·Chemical Communications : Chem Comm·Naoko KoteraMarie-Paule Teulade-Fichou
Jun 5, 2020·Chemistry : a European Journal·Aleksandr M AgafontsevEvgeny A Kataev
Oct 27, 2018·Scientific Reports·Abhijit SahaMarie-Paule Teulade-Fichou
Apr 25, 2020·ChemistryOpen·Mathieu Surin, Sébastien Ulrich
Aug 5, 2021·Journal of the American Chemical Society·Jérémie MitteauxDavid Monchaud
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Sep 28, 2018·Inorganic Chemistry·Moustafa T Gabr, F Christopher Pigge
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Jan 27, 2019·The Journal of Organic Chemistry·Vladimír CírkvaJan Storch
Aug 10, 2019·Journal of the American Chemical Society·Michaela KrafcikovaLukas Trantirek

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