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Molecules 2017, 22(11), 2005;

New Tripentone Analogs with Antiproliferative Activity

Department of Biological, Chemical, and Pharmaceutical Sciences and Technologies (STEBICEF), University of Palermo, via Archirafi 32, 90123 Palermo, Italy
Author to whom correspondence should be addressed.
Received: 27 October 2017 / Revised: 16 November 2017 / Accepted: 17 November 2017 / Published: 18 November 2017
(This article belongs to the Special Issue The Biomedical Importance of Indoles and Their Derivatives)
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Tripentones represent an interesting class of compounds due to their significant cytotoxicity against different human tumor cells in the submicro-nanomolar range. New tripentone analogs, in which a pyridine moiety replaces the thiophene ring originating the fused azaindole system endowed with anticancer activity viz 8H-thieno[2,3-b]pyrrolizinones, were efficiently synthesized in four steps with fair overall yields (34–57%). All tripentone derivatives were tested in the range of 0.1–100 μM for cytotoxicity against two human tumor cell lines, HCT-116 (human colorectal carcinoma) and MCF-7 (human breast cancer). The most active derivative, with GI50 values of 4.25 µM and 20.73 µM for HCT-116 and MCF-7 cells, respectively, did not affect the viability of Caco-2 differentiated in normal intestinal-like cells, suggesting tumor cells as the main target of its cytotoxic action. The same compound was further investigated in order to study its mode of action. Results showed that it did not exert necrotic effects, while induced a clear shift of viable cells towards early apoptosis. Flow cytometric analysis demonstrated that this compound caused cell cycle alteration, inhibiting its progression in S and G2/M phases. View Full-Text
Keywords: tripentones; aza-indoles; 8H-thieno[2,3-b]pyrrolizinones; antitumor activity; proapoptotic agents tripentones; aza-indoles; 8H-thieno[2,3-b]pyrrolizinones; antitumor activity; proapoptotic agents

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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 (CC BY 4.0).

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Parrino, B.; Ullo, S.; Attanzio, A.; Spanò, V.; Cascioferro, S.; Montalbano, A.; Barraja, P.; Tesoriere, L.; Cirrincione, G.; Diana, P. New Tripentone Analogs with Antiproliferative Activity. Molecules 2017, 22, 2005.

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