title: A para-amino substituent on the D-ring of green tea polyphenol epigallocatechin-3-gallate as a novel proteasome inhibitor and cancer cell apoptosis inducer.
abstract: Analogs of (-)-EGCG containing a para-amino group on the D-ring in place of the hydroxyl groups have been synthesized and their proteasome inhibitory activities were studied. We found that, the O-acetylated (-)-EGCG analogs possessing a p-NH(2) or p-NHBoc (Boc; tert-butoxycarbonyl) D-ring (5 and 7) act as novel tumor cellular proteasome inhibitors and apoptosis inducers with potency similar to natural (-)-EGCG and similar to (-)-EGCG peracetate. These data suggest that the acetylated amino-GTP analogs have the potential to be developed into novel anticancer agents.
authors.affiliation: Department of Applied Biology and Chemical Technology and the Open Laboratory of Chirotechnology, Institute of Molecular Technology for Drug Discovery and Synthesis, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, SAR, China.
authors.forename: Kumi
authors.initials: K
authors.lastname: Osanai
authors.forename: Kristin R
authors.initials: KR
authors.lastname: Landis-Piwowar
authors.forename: Q Ping
authors.initials: QP
authors.lastname: Dou
authors.forename: Tak Hang
authors.initials: TH
authors.lastname: Chan
mesh_terms: D017209:Apoptosis / Q000187:drug effects; D001402:B-Lymphocytes / Q000187:drug effects; D053148:Caspase 3 / Q000378:metabolism; D002392:Catechin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D006801:Humans; D007938:Leukemia / Q000188:drug therapy; D015394:Molecular Structure; D046988:Proteasome Endopeptidase Complex / Q000378:metabolism; D013329:Structure-Activity Relationship; D013662:Tea / Q000737:chemistry*
chemical_list: D013662:Tea; D002392:Catechin; C045651:epigallocatechin gallate; D053148:Caspase 3; D046988:Proteasome Endopeptidase Complex