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Int J Mol Sci. 2008 Jun;9(6):951-61. doi: 10.3390/ijms9060951. Epub 2008 Jun 2.

Prodrugs of fluoro-substituted benzoates of EGC as tumor cellular proteasome inhibitors and apoptosis inducers.

Author information

1
Barbara Ann Karmanos Cancer Institute, Department of Pathology, Wayne State University, Detroit, Michigan, USA. drzhiyongyu@yahoo.com.cn <drzhiyongyu@yahoo.com.cn>

Abstract

The most potent catechin in green tea is (-)-epigallocatechin-3-gallate [(-)-EGCG], which, however, is unstable under physiological conditions. To discover more stable and more potent polyphenol proteasome inhibitors, we synthesized several novel fluoro-substituted (-)-EGCG analogs, named F-EGCG analogs, as well as their prodrug forms with all of -OH groups protected by acetate. We report that the prodrug form of one F-EGCG analog exhibited greater potency than the previously reported peracetate of (-)-EGCG to inhibit proteasomal activity, suppress cell proliferation, and induce apoptosis in human leukemia Jurkat T cells, demonstrating the potential of these compounds to be developed into novel anti-cancer and cancer-preventive agents.

KEYWORDS:

cancer prevention; cancer therapy; prodrugs; proteasome inhibitors; tea polyphenols

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