Comparison of a pair of synthetic tea-catechin-derived epimers: synthesis, antifolate activity, and tyrosinase-mediated activation in melanoma |
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Authors: | Sáez-Ayala Magalí Sánchez-del-Campo Luis Montenegro María F Chazarra Soledad Tárraga Alberto Cabezas-Herrera Juan Rodríguez-López José Neptuno |
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Affiliation: | 1. Department of Biochemistry and Molecular Biology?A, School of Biology, University of Murcia, Avda. Teniente Flomesta, no. 5, 30003 Murcia (Spain), Fax: (+34)?868‐884147;2. Department of Organic Chemistry, Faculty of Chemistry, University of Murcia, Avda. Teniente Flomesta, no. 5, 30003 Murcia (Spain);3. Research Unit of Clinical Analysis Service, University Hospital “Virgen de?la Arrixaca”, Ctra. Madrid‐Cartagena, 30120 Murcia (Spain) |
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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. |
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Keywords: | antifolate activity epimers melanoma prodrugs tea catechins |
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