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Mar. Drugs 2019, 17(1), 35;

New 1,2,4-Oxadiazole Nortopsentin Derivatives with Cytotoxic Activity

Department of Biological, Chemical and Pharmaceutical Sciences and Technologies (STEBICEF), University of Palermo, via Archirafi 32, 90123 Palermo, Italy
Department of Pharmacy, University of Salerno, Via G. Paolo II 132, 84084 Fisciano, Italy
Author to whom correspondence should be addressed.
Received: 5 December 2018 / Revised: 28 December 2018 / Accepted: 4 January 2019 / Published: 8 January 2019
(This article belongs to the Special Issue Synthesis of marine natural products and analogues)
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New analogs of nortopsentin, a natural 2,4-bis(3′-indolyl)imidazole alkaloid, in which the central imidazole ring of the natural lead was replaced by a 1,2,4-oxadiazole moiety, and in which a 7-azaindole portion substituted the original indole moiety, were efficiently synthesized. Among all derivatives, prescreened against the HCT-116 colon rectal carcinoma cell line, the two most active compounds were selected and further investigated in different human tumor cells showing IC50 values in the micromolar and submicromolar range. Flow cytometric analysis of propidium iodide-stained MCF-7 cells demonstrated that both the active derivatives caused cell cycle arrest in the G0–G1 phase. The cell death mechanism induced by the compounds was considered to be apoptotic by measuring the exposure of phosphatidylserine to the outer membrane and observed morphological evaluation using acridine orange/ethidium bromide double staining. Moreover, further tested on intestinal normal-like differentiated Caco-2 cell line, they exhibited preferential toxicity towards cancer cells. View Full-Text
Keywords: marine alkaloids; nortopsentin analogs; 1,2,4-oxadiazole derivatives; anti-cancer agents; antiproliferative activity marine alkaloids; nortopsentin analogs; 1,2,4-oxadiazole derivatives; anti-cancer agents; antiproliferative activity

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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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Cascioferro, S.; Attanzio, A.; Di Sarno, V.; Musella, S.; Tesoriere, L.; Cirrincione, G.; Diana, P.; Parrino, B. New 1,2,4-Oxadiazole Nortopsentin Derivatives with Cytotoxic Activity. Mar. Drugs 2019, 17, 35.

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