Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
(−)-EGCG, the most abundant catechin, was found to be chemopreventive and anticancer agent. However, (−)-EGCG has at least one limitation: it gives poor bioavailability. This invention provides compounds of generally formula 10, wherein R1is selected from the group of —H and C1to C6acyl group; R2, R3, and R4are each independently selected from the group of —H, —OH, and C1to C6acyloxyl group; and at least one of R2, R3, or R4is —H. The derivatives of (−)-EGCG that is at least as potent as (−)-EGCG. The carboxylate protected forms of (−)-EGCG and its derivatives are found to be more stable than the unprotected forms, which can be used as proteasome inhibitors to reduce tumor cell growth.
patent: 10-254087 (1998-09-01), None
patent: WO 99/22728 (1999-05-01), None
Kuhn, D et al Synthetic peracetate Tea Polyphenols as Potent Proteasome Inhibitirs and Apoptosis Inducers in Human Cancer Cells Frontiers in Bioscience 10, 1010-23, May 1, 2005.
Kohri, T et al Synthesis of (−)-[4-H]Epigallocatechin Gallate and its Metabic Fate in Rates after Intravenous Administration J.Agric. Food Chem, 2001,49,1042-1048.
Hiipakka, RA et al Sturcture-activity relationships for inhibition of human 5£-reductases by polyphenols Biochemical Pharmacology 63 (2002) 1165-1176.
Kreimeyer, J et al ‘Separations of flavan-3-ols and dimeric proanthocyanidins by capillary electrophoresis’ CA 128:221701 (1998).
Andreas, D et al ‘Flavan-3-ols, prodelphinidins and further polyphenols from cistus salvifolius’ CA 122:5467 (1995).
Smith, DM et al Synthetic Analogs of Green Tea Polyphenols as Proteasome Inhibitiors Molecular Medicine 8(7), 382-392 (2002).
Smith, Docking studies and model development of tea polyphenol proteasome inhibitors: applications to rational drug design, Proteins: Structure, Function and Bioinformatics 54:58-70 (2004).
Nam, Ester bond-containing tea polyphenols potently inhibit proteasome activity in vitro and in vivo, J. Biol. Chem (2001) 276(16) 13322-13330.
Kazi, Potential molecular targets of tea polyphenols in human tumor cells: significance in cancer proliferation. PMID: 12494882 (2002).
Jung et al, Inhibition of tumor invasion and angiogenesis by epigalocatechin gallage (EGCG), a major component of green tea,International Journal of Experiental Pathology, 52,309-316 (2001).
U.S. Appl. No. 11/600,513, filed Feb. 2007, Chan.
Danne et al,Phytochemistry, “Flavan-3-ols, Prodelphinidins and Further Polyphenols fromCistus Salvifolius,” vol. 37, No. 2 (1994), pp. 533-538.
Wang et al,Natural Product Research and Development, “The synthesis of liposoluble tea polyphenols (LTP) and its resistance to autoxidation of oil,” vol. 13, No. 4 (2001), pp. 12-15 (with abstract).
Wang et al,Fine Chemicals, “Synthesis of liposoluble tea polyphenols with varying aliphatic groups and their antioxidation activity,” vol. 19, No. 2 (2002), pp. 86-89 (with abstract).
De Groot et al,Bulletin of Magnetic Resonance, “Advantages of Long-Range-Inept Measurements for Structure Determination of Catechin Esters,” vol. 17, No. 1-4 (1995), pp. 242-243.
Lam et al,Bioorganic&Medicinal Chemistry, “A potential prodrug for a green tea polyphenol proteasome inhibitor: evaluation of the peracetate ester of (−)-epigallocatechin gallate [(-)-EGCG],” vol. 12, No. 21 (2004), pp. 5587-5593.
Chow Larry Ming-Cheung
Dou Qing Ping
Kuhn Deborah Joyce
Buchanan & Ingersoll & Rooney PC
Seaman D. Margaret
The Hong Kong Polytechnic University
University of South Florida
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