3024-25-7Relevant articles and documents
Antiproliferative properties and g-quadruplex-binding of symmetrical naphtho[1,2-b:8,7-b’]dithiophene derivatives
Almerico, Anna Maria,Barone, Giampaolo,Bono, Alessia,Bonsignore, Riccardo,Gentile, Carla,La Monica, Gabriele,Lauria, Antonino,Mannino, Giuseppe,Martorana, Annamaria,Terenzi, Alessio
, (2021)
Background: G-quadruplex (G4) forming sequences are recurrent in telomeres and promoter regions of several protooncogenes. In normal cells, the transient arrangements of DNA in G-tetrads may regulate replication, transcription, and translation processes. Tumors are character-ized by uncontrolled cell growth and tissue invasiveness and some of them are possibly mediated by gene expression involving G-quadruplexes. The stabilization of G-quadruplex sequences with small molecules is considered a promising strategy in anticancer targeted therapy. Methods: Molecular virtual screening allowed us identifying novel symmetric bifunctionalized naphtho[1,2-b:8,7-b’]dithiophene ligands as interesting candidates targeting h-Telo and c-MYC G-quadruplexes. A set of unexplored naphtho-dithiophene derivatives has been synthesized and biologically tested through in vitro antiproliferative assays and spectroscopic experiments in solution. Results: The analysis of biological and spectroscopic data highlighted noteworthy cytotoxic effects on HeLa cancer cell line (GI50 in the low μM range), but weak interactions with G-quadruplex c-MYC promoter. Conclusions: The new series of naphtho[1,2-b:8,7-b’]dithiophene derivatives, bearing the pharmacophoric assump-tions necessary to stabilize G-quadruplexes, have been designed and successfully synthesized. The interesting antiproliferative results supported by computer aided rational approaches suggest that these studies are a significant starting point for a lead optimization process and the isolation of a more efficacious set of G-quadruplexes stabilizers.
HALOGENATION REGIOSELECTIVE EN SERIE AROMATIQUE-II CHLORATION DES NAPHTOLS ET LEURS ETHERS A L'AIDE DE REACTIFS METTANT EN JEU DES INTERACTIONS DU TYPE DONNEUR-ACCEPTEUR
Guy, Alain,Lemaire, Marc,Guette, Jean-Paul
, p. 2347 - 2354 (2007/10/02)
The regispecific chlorination of naphtols by hexachlorocyclohexadienones as selective chlorinating reagents is described.The selectivity attained is better than that which we have obtained with phenol derivatives and confirms the importance of the donor-acceptor interaction between the reagent and the naphthol during the chlorination.
