title: Anticancer activity of 3-O-acyl and alkyl-(-)-epicatechin derivatives.
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.
authors.affiliation: Laboratory of Cellular Function Modulator, Korea Research Institute of Bioscience and Biotechnology, Yusung, Taejon 305-333, Korea. pkduck75@hanmail.net
authors.forename: Ki Duk
authors.initials: KD
authors.lastname: Park
authors.forename: Sul Gi
authors.initials: SG
authors.lastname: Lee
authors.forename: Sung Uk
authors.initials: SU
authors.lastname: Kim
authors.forename: Sung Han
authors.initials: SH
authors.lastname: Kim
authors.forename: Won Suck
authors.initials: WS
authors.lastname: Sun
authors.forename: Sung Jin
authors.initials: SJ
authors.lastname: Cho
authors.forename: Do Hyeon
authors.initials: DH
authors.lastname: Jeong
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology*; D028241:Camellia sinensis / Q000737:chemistry; D002392:Catechin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D004355:Drug Stability; D006801:Humans; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D002392:Catechin