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Prodrugs of Fluoro-Substituted Benzoates of EGC as Tumor Cellular Proteasome Inhibitors and Apoptosis Inducers
The Prevention Program, Barbara Ann Karmanos Cancer Institute, and Department of Pathology, School of Medicine, Wayne State University, Detroit, Michigan, USA
Key Laboratory of Marine Drug, Ministry of Education, Medical College, Ocean University of China, Qingdao, China.
Shandong Tumor Hospital & Institute, Breast Cancer Center, Jinan, Shandong, China
* Author to whom correspondence should be addressed.
Received: 1 April 2008; in revised form: 12 May 2008 / Accepted: 26 May 2008 / Published: 2 June 2008
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: tea polyphenols; prodrugs; proteasome inhibitors; cancer prevention; cancer therapy
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Yu, Z.; Qin, X.L.; Gu, Y.Y.; Chen, D.; Cui, Q.C.; Jiang, T.; Wan, S.B.; Dou, Q.P. Prodrugs of Fluoro-Substituted Benzoates of EGC as Tumor Cellular Proteasome Inhibitors and Apoptosis Inducers. Int. J. Mol. Sci. 2008, 9, 951-961.
Yu Z, Qin XL, Gu YY, Chen D, Cui QC, Jiang T, Wan SB, Dou QP. Prodrugs of Fluoro-Substituted Benzoates of EGC as Tumor Cellular Proteasome Inhibitors and Apoptosis Inducers. International Journal of Molecular Sciences. 2008; 9(6):951-961.
Yu, Zhiyong; Qin, Xu L.; Gu, Yan Y.; Chen, Di; Cui, Qiuzhi C.; Jiang, Tao; Wan, Sheng B.; Dou, Q. P. 2008. "Prodrugs of Fluoro-Substituted Benzoates of EGC as Tumor Cellular Proteasome Inhibitors and Apoptosis Inducers." Int. J. Mol. Sci. 9, no. 6: 951-961.