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Journal of Nucleic Acids
Volume 2010, Article ID 525862, 19 pages
http://dx.doi.org/10.4061/2010/525862
Review Article

One Ring to Bind Them All”—Part I: The Efficiency of the Macrocyclic Scaffold for G-Quadruplex DNA Recognition

1Section Recherche, Institut Curie, CNRS UMR176, Centre Universitaire Paris XI, Batiment 110, 91405 Orsay, France
2Institut de Chimie Moléculaire, CNRS UMR5260, Université de Bourgogne, 21000 Dijon, France
3Acides Nucléiques : Dynamique, Ciblage et Fonctions Biologiques, Laboratoire des Régulations et Dynamique du Génome, CNRS, UMR5153, INSERM U565, Muséum National d'Histoire Naturelle USM 503, 43 Rue Cuvier, 75005 Paris, France
4Institut Européen de Chimie et Biologie, INSERM U869, Université de Bordeaux, 33607 Pessac Cedex, France

Received 29 January 2010; Accepted 18 February 2010

Academic Editor: R. Eritja

Copyright © 2010 David Monchaud et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Macrocyclic scaffolds are particularly attractive for designing selective G-quadruplex ligands essentially because, on one hand, they show a poor affinity for the “standard” B-DNA conformation and, on the other hand, they fit nicely with the external G-quartets of quadruplexes. Stimulated by the pioneering studies on the cationic porphyrin TMPyP4 and the natural product telomestatin, follow-up studies have developed, rapidly leading to a large diversity of macrocyclic structures with remarkable-quadruplex binding properties and biological activities. In this review we summarize the current state of the art in detailing the three main categories of quadruplex-binding macrocycles described so far (telomestatin-like polyheteroarenes, porphyrins and derivatives, polyammonium cyclophanes), and in addressing both synthetic issues and biological aspects.