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Xanthene and xanthone derivatives as G-quadruplex stabilizing ligands.

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.

SUBMITTER: Altieri A

PROVIDER: S-EPMC6269716 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Xanthene and xanthone derivatives as G-quadruplex stabilizing ligands.

Altieri Alessandro A Alvino Antonello A Ohnmacht Stephan S Ortaggi Giancarlo G Neidle Stephen S Nocioni Daniele D Franceschin Marco M Bianco Armandodoriano A

Molecules (Basel, Switzerland) 20131030 11

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 fo ...[more]

PMID: 24177701

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