A new series of nortopsentin analogues, in which the imidazole ring of the natural product was replaced by thiazole and the indole unit bound to position 2 of the thiazole ring was substituted by a 7-azaindole moiety, was efficiently synthesized. Two of the new nortopsentin analogues showed good antiproliferative effect against the totality of the NCI full panel of human tumor cell lines (∼60) having GI50 values ranging from low micromolar to nanomolar level. The mechanism of the antiproliferative effect of these derivatives, investigated on human hepatoma HepG2 cells, was pro-apoptotic, being associated with externalization of plasma membrane phosphatidylserine and mitochondrial dysfunction. Moreover, the compounds induced a concentration-dependent accumulation of cells in the subG0/G1phase, while confined viable cells in G2/M phase.

Parrino, B., Carbone, A., Di Vita, G., Ciancimino, C., Attanzio, A., Spanò, V., et al. (2015). 3-[4-(1H-indol-3-yl)-1,3-thiazol-2-yl]-1H-pyrrolo[2,3-b]pyridines, nortopsentin Analogues with antiproliferative activity. MARINE DRUGS, 13(4), 1901-1924 [10.3390/md13041901].

3-[4-(1H-indol-3-yl)-1,3-thiazol-2-yl]-1H-pyrrolo[2,3-b]pyridines, nortopsentin Analogues with antiproliferative activity

PARRINO, Barbara;CARBONE, Anna;DI VITA, Gloria;CIANCIMINO, Cristina;ATTANZIO, Alessandro;SPANO', Virginia;MONTALBANO, Alessandra;BARRAJA, Paola;TESORIERE, Luisa;LIVREA, Maria Antonia;DIANA, Patrizia;CIRRINCIONE, Girolamo
2015-04-03

Abstract

A new series of nortopsentin analogues, in which the imidazole ring of the natural product was replaced by thiazole and the indole unit bound to position 2 of the thiazole ring was substituted by a 7-azaindole moiety, was efficiently synthesized. Two of the new nortopsentin analogues showed good antiproliferative effect against the totality of the NCI full panel of human tumor cell lines (∼60) having GI50 values ranging from low micromolar to nanomolar level. The mechanism of the antiproliferative effect of these derivatives, investigated on human hepatoma HepG2 cells, was pro-apoptotic, being associated with externalization of plasma membrane phosphatidylserine and mitochondrial dysfunction. Moreover, the compounds induced a concentration-dependent accumulation of cells in the subG0/G1phase, while confined viable cells in G2/M phase.
Settore CHIM/08 - Chimica Farmaceutica
https://www.mdpi.com/1660-3397/13/4/1901; http://www.mdpi.com/1660-3397/13/4/1901/pdf
Parrino, B., Carbone, A., Di Vita, G., Ciancimino, C., Attanzio, A., Spanò, V., et al. (2015). 3-[4-(1H-indol-3-yl)-1,3-thiazol-2-yl]-1H-pyrrolo[2,3-b]pyridines, nortopsentin Analogues with antiproliferative activity. MARINE DRUGS, 13(4), 1901-1924 [10.3390/md13041901].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/145699
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