Publication: Synthesis and Biological Activity of a 3,4,5-Trimethoxybenzoyl Ester Analogue of Epicatechin-3-gallate
Authors
Otón Vidal, Francisco ; Tárraga Tomás, Alberto ; Cabezas Herrera, Juan ; Chazarra Parres, Soledad ; Rodríguez López, José Neptuno ; Sánchez del Campo Ferrer, Luis
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Publisher
AMER CHEMICAL SOC
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DOI
https://doi.org/10.1021/jm701346h
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info:eu-repo/semantics/article
Description
©2008. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
This document is the Accepted version of a Published Work that appeared in final form in Journal of Medicinal Chemistry. To access the final edited and published work see https://doi.org/10.1021/jm701346h
Abstract
Despite presenting bioavailability problems, tea catechins have emerged as promising chemopreventive agents because of their observed efficacy in various animal models. To improve the stability and cellular absorption of tea polyphenols, we developed a new catechin-derived compound, 3-O-(3,4,5-trimethoxybenzoyl)-(-)-epicatechin (TMECG), which has shown significant antiproliferative activity against several cancer cell lines, especially melanoma. The presence of methoxy groups in its ester-bound gaily] moiety drastically decreased its antioxidant and prooxidant properties without affecting its cell-antiproliferative effects, and the data indicated that the 3-gallyl moiety was essential for its biological activity. As regards its action mechanism, we demonstrated that TMECG binds efficiently to human dihydrofolate reductase and down-regulates folate cycle gene expression in melanoma cells. Disruption of the folate cycle by TMECG is a plausible explanation for its observed biological effects and suggests that, like other antifolate compounds, TMECG could be of clinical value in cancer therapy.
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Citation
Journal of Medicinal Chemistry. Volumen 51. nº7. Paginas 2018-2026
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