Anticancer activity of 3-O-acyl and alkyl-(-)-epicatechin derivatives

Bioorganic & Medicinal Chemistry Letters
Ki Duk ParkDo Hyeon Jeong

Abstract

By changing the structure or replacing the gallate group of (-)-ECG, 3-O-acyl and alkyl-(-)-epicatechin derivatives were synthesized to be screen as anticancer agents using the MTT assay in vitro against cancer cell lines (PC3, SKOV3, U373MG). 3-O-Acyl and alkyl-(-)-epicatechin derivatives (4-25) exhibited better anticancer activity than (-)-ECG and specially, compounds 6-8, 17-19, which were modified aliphatic chains with moderate sizes (C8-C12) showed strong anticancer activity (IC50=6.4-31.2 microM). The introduction of an alkyloxy group on 3-O-hydroxyl instead of an acyloxy group significantly enhanced inhibitory activity. Consequently, the compound that showed the most potency as anticancer agents were 3-O-decyl-(-)-epicatechin (18) (IC50=8.9, 7.9, 6.4 microM against PC3, SKOV3, U373MG, respectively), which modified the appropriate lipophilic group on the C-3 hydroxyl as an alkyloxy group.

Citations

Jul 13, 2013·Journal of Natural Medicines·Raushanara AkterEvelin Tiralongo
Jul 22, 2011·Food & Function·Manabu UedaHitoshi Ashida
Aug 27, 2009·Evidence-based Complementary and Alternative Medicine : ECAM·Shaikh J UddinEvelin Tiralongo
Sep 19, 2012·Evidence-based Complementary and Alternative Medicine : ECAM·S SahaD Nath
Jul 19, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Magalí Sáez-AyalaJosé Neptuno Rodríguez-López
Mar 7, 2021·Pharmaceuticals·Paula Garcia-OliveiraMiguel Angel Prieto
Mar 8, 2008·Journal of Medicinal Chemistry·Luís Sánchez-del-CampoJosé Neptuno Rodríguez-López

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