Molecules 2013, 18(11), 13446-13470; doi:10.3390/molecules181113446

Xanthene and Xanthone Derivatives as G-Quadruplex Stabilizing Ligands

1,* email, 1email, 2email, 1email, 2email, 1email, 1email and 1,* email
Received: 27 September 2013; in revised form: 21 October 2013 / Accepted: 23 October 2013 / Published: 30 October 2013
(This article belongs to the Special Issue G-Quadruplexes & i-Motif DNA)
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: 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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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.

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