Abstract
Despite bioavailability issues, tea catechins have emerged as promising chemopreventive agents because of their efficacy in various animal models. We synthesized two catechin-derived compounds, 3-O-(3,4,5-trimethoxybenzoyl)-(-)-catechin (TMCG) and 3-O-(3,4,5-trimethoxybenzoyl)-(-)-epicatechin (TMECG), in an attempt to improve the stability and cellular absorption of tea polyphenols. The antiproliferative and pro-apoptotic activities of both compounds were analyzed with various cancer cell systems, and TMCG, which was easily synthesized in excellent yield, was more active than TMECG in both melanoma and non-melanoma cell lines. TMCG was also a better inhibitor of dihydrofolate reductase and was more efficiently oxidized by tyrosinase, potentially explaining the difference in activity between these epimers.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry*
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Antineoplastic Agents / therapeutic use
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Antioxidants / chemical synthesis
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Antioxidants / chemistry
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Antioxidants / therapeutic use
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Catechin / analogs & derivatives*
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Catechin / chemical synthesis
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Catechin / chemistry
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Catechin / therapeutic use
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Cell Line, Tumor
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Folic Acid Antagonists / chemical synthesis*
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Folic Acid Antagonists / chemistry
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Folic Acid Antagonists / therapeutic use
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Humans
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Hydrogen-Ion Concentration
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Melanoma / drug therapy*
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Models, Molecular
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Monophenol Monooxygenase / chemistry*
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Monophenol Monooxygenase / metabolism
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Oxidation-Reduction
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Stereoisomerism
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Tea / chemistry
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Tetrahydrofolate Dehydrogenase / chemistry
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Tetrahydrofolate Dehydrogenase / metabolism
Substances
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3-O-(3,4,5-trimethoxybenzoyl)catechin
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3-O-(3,4,5-trimethoxybenzoyl)epicatechin
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Antineoplastic Agents
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Antioxidants
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Folic Acid Antagonists
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Tea
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Catechin
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Monophenol Monooxygenase
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Tetrahydrofolate Dehydrogenase