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Xanthene and Xanthone Derivatives as G-Quadruplex Stabilizing Ligands
Dipartimento di Chimica, Università di Roma "La Sapienza", Piazzale Aldo Moro 5, Roma 00185, Italy
The UCL School of Pharmacy, University College London, 29-39 Brunswick Square, London WC1N 1AX, UK
* Authors to whom correspondence should be addressed.
Received: 27 September 2013; in revised form: 21 October 2013 / Accepted: 23 October 2013 / Published: 30 October 2013
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.
Keywords: G-quadruplex; xanthene; xanthone; ESI-MS; FRET; telomere; c-myc; bcl-2
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Altieri, A.; Alvino, A.; Ohnmacht, S.; Ortaggi, G.; Neidle, S.; Nocioni, D.; Franceschin, M.; Bianco, A. Xanthene and Xanthone Derivatives as G-Quadruplex Stabilizing Ligands. Molecules 2013, 18, 13446-13470.
Altieri A, Alvino A, Ohnmacht S, Ortaggi G, Neidle S, Nocioni D, Franceschin M, Bianco A. Xanthene and Xanthone Derivatives as G-Quadruplex Stabilizing Ligands. Molecules. 2013; 18(11):13446-13470.
Altieri, Alessandro; Alvino, Antonello; Ohnmacht, Stephan; Ortaggi, Giancarlo; Neidle, Stephen; Nocioni, Daniele; Franceschin, Marco; Bianco, Armandodoriano. 2013. "Xanthene and Xanthone Derivatives as G-Quadruplex Stabilizing Ligands." Molecules 18, no. 11: 13446-13470.