Structure-activity study of epi-gallocatechin gallate (EGCG) analogs as proteasome inhibitors

Sheng Biao Wan; Kristin R Landis-Piwowar; Deborah J Kuhn; Di Chen; Q Ping Dou; Tak Hang Chan

doi:10.1016/j.bmc.2004.12.056

Structure-activity study of epi-gallocatechin gallate (EGCG) analogs as proteasome inhibitors

Bioorg Med Chem. 2005 Mar 15;13(6):2177-85. doi: 10.1016/j.bmc.2004.12.056.

Authors

Sheng Biao Wan¹, Kristin R Landis-Piwowar, Deborah J Kuhn, Di Chen, Q Ping Dou, Tak Hang Chan

Affiliation

¹ 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.

PMID: 15727870
DOI: 10.1016/j.bmc.2004.12.056

Abstract

The structure-activity relationship of a number of synthetic green tea polyphenol analogs involving modifications of A ring and B ring of epi-gallocatechin gallate (EGCG) as proteasome inhibitors has been examined. It was found that in B ring, a decrease in the number of OH groups led to decreased potency. Introduction of a hydrophobic benzyl group into the 8 position of A ring did not significantly affect the proteasome-inhibitory potency.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Catechin / analogs & derivatives*
Catechin / chemical synthesis
Catechin / chemistry*
Catechin / pharmacology*
Flavonoids / chemical synthesis
Flavonoids / chemistry
Flavonoids / pharmacology
Inhibitory Concentration 50
Molecular Structure
Phenols / chemical synthesis
Phenols / chemistry
Phenols / pharmacology
Polyphenols
Proteasome Endopeptidase Complex / metabolism
Proteasome Inhibitors*
Stereoisomerism
Structure-Activity Relationship
Tea / chemistry*

Substances

Flavonoids
Phenols
Polyphenols
Proteasome Inhibitors
Tea
gallocatechin gallate
Catechin
Proteasome Endopeptidase Complex