Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/9484
Title: A potential prodrug for a green tea polyphenol proteasome inhibitor : evaluation of the peracetate ester of (-)-epigallocatechin gallate [(-)-EGCG]
Authors: Lam, WH
Kazi, A
Kuhn, DJ
Chow, LMC 
Chan, ASC
Dou, QP
Chan, TH
Issue Date: 2004
Source: Bioorganic and medicinal chemistry, 2004, v. 12, no. 21, p. 5587-5593 How to cite?
Journal: Bioorganic and Medicinal Chemistry 
Abstract: Green tea has been shown to have many biological effects, including effects on metabolism, angiogenesis, oxidation, and cell proliferation. Unfortunately, the most abundant green tea polyphenol (-)-epigallocatechin gallate or (-)-EGCG is very unstable in neutral or alkaline medium. This instability leads to a low bioavailability. In an attempt to enhance the stability of (-)-EGCG, we introduced peracetate protection groups on the reactive hydroxyls of (-)-EGCG (noted in text as 1). HPLC analysis shows that the protected (-)-EGCG analog is six times more stable than natural (-)-EGCG under slightly alkaline conditions. A series of bioassays show that 1 has no inhibitory activity against a purified 20S proteasome in vitro, but exhibits increased proteasome-inhibitory activity in intact leukemic cells over natural (-)-EGCG, indicating an intercellular conversion. Inhibition of cellular proteasome activity by 1 is associated with induction of cell death. Therefore, our results indicate that the protected analog 1 may function as a prodrug of the green tea polyphenol proteasome inhibitor (-)-EGCG.
URI: http://hdl.handle.net/10397/9484
ISSN: 0968-0896
DOI: 10.1016/j.bmc.2004.08.002
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