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.
Xanthene and Xanthone Derivatives as G-Quadruplex Stabilizing Ligands / Altieri, Alessandro; Alvino, Antonello; Stephan, Ohnmacht; Ortaggi, Giancarlo; Stephen, Neidle; Daniele, Nocioni; Marco, Franceschin; Bianco, Armandodoriano. - In: MOLECULES. - ISSN 1420-3049. - STAMPA. - 18:11(2013), pp. 13446-13470. [10.3390/molecules181113446]
Xanthene and Xanthone Derivatives as G-Quadruplex Stabilizing Ligands
ALTIERI, ALESSANDRO;ALVINO, Antonello;ORTAGGI, Giancarlo;BIANCO, Armandodoriano
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.