Abstract
Following the results we previously reported on a series of xanthene and xanthone derivatives as G-quadruplex stabilizing ligands, in order to obtain a more selective compound with respect to the previous generation of derivatives, we decided to modify the structure of the core ligand, specifically its aromatic extension. In particular, here we report the design, synthesis and activity data of a new compound obtained by dimerization of the xanthene core (HELIXA4C). The reported results show that extension of the aromatic core and the increase of the number of polar side chains led to a great enhancement of G-quadruplex selectivity and telomere damage capability, as derived using ESI-MS evaluation, in vitro cancer screening and specific immunofluorescence assays.
| Original language | English |
|---|---|
| Pages (from-to) | 9572-9582 |
| Number of pages | 11 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 12 |
| Issue number | 47 |
| DOIs | |
| Publication status | Published - Dec 21 2014 |
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ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Biochemistry
- Medicine(all)
Cite this
Design and synthesis of a new dimeric xanthone derivative : Enhancement of G-quadruplex selectivity and telomere damage. / Franceschin, Marco; Nocioni, Daniele; Biroccio, Annamaria; Micheli, Emanuela; Cacchione, Stefano; Cingolani, Chiara; Venditti, Alessandro; Zizza, Pasquale; Bianco, Armandodoriano; Altieri, Alessandro.
In: Organic and Biomolecular Chemistry, Vol. 12, No. 47, 21.12.2014, p. 9572-9582.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Design and synthesis of a new dimeric xanthone derivative
T2 - Enhancement of G-quadruplex selectivity and telomere damage
AU - Franceschin, Marco
AU - Nocioni, Daniele
AU - Biroccio, Annamaria
AU - Micheli, Emanuela
AU - Cacchione, Stefano
AU - Cingolani, Chiara
AU - Venditti, Alessandro
AU - Zizza, Pasquale
AU - Bianco, Armandodoriano
AU - Altieri, Alessandro
PY - 2014/12/21
Y1 - 2014/12/21
N2 - Following the results we previously reported on a series of xanthene and xanthone derivatives as G-quadruplex stabilizing ligands, in order to obtain a more selective compound with respect to the previous generation of derivatives, we decided to modify the structure of the core ligand, specifically its aromatic extension. In particular, here we report the design, synthesis and activity data of a new compound obtained by dimerization of the xanthene core (HELIXA4C). The reported results show that extension of the aromatic core and the increase of the number of polar side chains led to a great enhancement of G-quadruplex selectivity and telomere damage capability, as derived using ESI-MS evaluation, in vitro cancer screening and specific immunofluorescence assays.
AB - Following the results we previously reported on a series of xanthene and xanthone derivatives as G-quadruplex stabilizing ligands, in order to obtain a more selective compound with respect to the previous generation of derivatives, we decided to modify the structure of the core ligand, specifically its aromatic extension. In particular, here we report the design, synthesis and activity data of a new compound obtained by dimerization of the xanthene core (HELIXA4C). The reported results show that extension of the aromatic core and the increase of the number of polar side chains led to a great enhancement of G-quadruplex selectivity and telomere damage capability, as derived using ESI-MS evaluation, in vitro cancer screening and specific immunofluorescence assays.
UR - http://www.scopus.com/inward/record.url?scp=84909987653&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84909987653&partnerID=8YFLogxK
U2 - 10.1039/c4ob01658k
DO - 10.1039/c4ob01658k
M3 - Article
C2 - 25363232
AN - SCOPUS:84909987653
VL - 12
SP - 9572
EP - 9582
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 47
ER -