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Xanthene and Xanthone Derivatives as G-Quadruplex Stabilizing Ligands

By Alessandro Altieri, Antonello Alvino, Stephan Ohnmacht, Giancarlo Ortaggi, Stephen Neidle, Daniele Nocioni, Marco Franceschin and Armandodoriano Bianco

Abstract

Following previous studies on anthraquinone and acridine-based G-quadruplex ligands, here we present a study of similar aromatic cores, with the specific aim of increasing G-quadruplex binding and selectivity with respect to duplex DNA. Synthesized compounds include two and three-side chain xanthone and xanthene derivatives, as well as a dimeric “bridged” form. ESI and FRET measurements suggest that all the studied molecules are good G-quadruplex ligands, both at telomeres and on G-quadruplex forming sequences of oncogene promoters. The dimeric compound and the three-side chain xanthone derivative have been shown to represent the best compounds emerging from the different series of ligands presented here, having also high selectivity for G-quadruplex structures with respect to duplex DNA. Molecular modeling simulations are in broad agreement with the experimental data

Topics: G-quadruplex, xanthene, xanthone, ESI-MS, FRET, telomere, c-myc, bcl-2, Organic chemistry, QD241-441, Chemistry, QD1-999, Science, Q, DOAJ:Organic Chemistry, DOAJ:Chemistry
Publisher: MDPI AG
Year: 2013
DOI identifier: 10.3390/molecules181113446
OAI identifier: oai:doaj.org/article:1695155e35b84d6f9727c48887f20964
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