Anticancer activity of 3-O-acyl and alkyl-(-)-epicatechin derivatives.
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.
Park
Ki Duk
KD
Laboratory of Cellular Function Modulator, Korea Research Institute of Bioscience and Biotechnology, Yusung, Taejon 305-333, Korea. pkduck75@hanmail.net
Lee
Sul Gi
SG
Kim
Sung Uk
SU
Kim
Sung Han
SH
Sun
Won Suck
WS
Cho
Sung Jin
SJ
Jeong
Do Hyeon
DH
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
D000970:Antineoplastic Agents; D002392:Catechin