Synthesis and Biological Evaluation of Furanoallocolchicinoids

Yuliya Voitovich Ekaterina Shegravina Nikolay Sitnikov Vladimir Faerman Valery Fokin Hans-Gunther Schmalz Sébastien Combes 1 Diane Allegro 2 Pascale Barbier 2 Irina Beletskaya 3 Elena Svirshchevskaya 4 Alexey Yu Fedorov Alexey Yu. Fedorov
1 ICR - Institut de Chimie Radicalaire
2 CRO2 - Centre de Recherches en Oncologie biologique et Oncopharmacologie
3 MSU - Lomonosov Moscow State University
4 Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry
Abstract : A series of conformationally flexible furan-derived allocolchicinoids was prepared from commercially available colchicine in good to excellent yields using a three-step reaction sequence. Cytotoxicity studies indicated the potent activity of two compounds against human epithelial and lymphoid cell lines (AsPC-1, HEK293, and Jurkat) as well as against Wnt-1 related murine epithelial cell line W1308. The results of in vitro experiments demonstrated that the major effect of these compounds was the induction of cell cycle arrest in the G2/M phase as a direct consequence of effective tubulin binding. In vivo testing of the most potent furanoallocolchicinoid 10c using C57BL/6 mice inoculated with Wnt-1 tumor cells indicated significant inhibition of the tumor growth.
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Submitted on : Tuesday, March 27, 2018 - 2:49:03 PM
Last modification on : Wednesday, September 4, 2019 - 5:36:02 PM

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Yuliya Voitovich, Ekaterina Shegravina, Nikolay Sitnikov, Vladimir Faerman, Valery Fokin, et al.. Synthesis and Biological Evaluation of Furanoallocolchicinoids. Journal of Medicinal Chemistry, American Chemical Society, 2014, 58 (2), pp.692 - 704. ⟨10.1021/jm501678w⟩. ⟨hal-01744566⟩

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