Publication:
Synthesis and Biological Activity of a 3,4,5-Trimethoxybenzoyl Ester Analogue of Epicatechin-3-gallate

Simple item page
dc.contributor.authorOtón Vidal, Francisco
dc.contributor.authorTárraga Tomás, Alberto
dc.contributor.authorCabezas Herrera, Juan
dc.contributor.authorChazarra Parres, Soledad
dc.contributor.authorRodríguez López, José Neptuno
dc.contributor.authorSánchez del Campo Ferrer, Luis
dc.contributor.departmentBioquímica y Biología Molecular Aes
dc.date.accessioned2023-12-22T11:07:33Z
dc.date.available2023-12-22T11:07:33Z
dc.date.issued2008-04-10
dc.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/jm701346hes
dc.description.abstractDespite 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.es
dc.formatapplication/pdfes
dc.format.extent38es
dc.identifier.citationJournal of Medicinal Chemistry. Volumen 51. nº7. Paginas 2018-2026
dc.identifier.doihttps://doi.org/10.1021/jm701346h
dc.identifier.issn0022-2623
dc.identifier.issn1520-4804
dc.identifier.urihttp://hdl.handle.net/10201/136888
dc.languageenges
dc.publisherAMER CHEMICAL SOCes
dc.relationÁmbito del proyecto: Nacional y regional. Agencia financiadora: Ministerio de Educación y Ciencia y Fundación Séneca (CARM) Código o número del acuerdo de subvención: SAF2006-07040-C02-01, SAF2006-07040-C02-02, 02970/PI/05es
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.subjectTeaes
dc.subjectAcido fólicoes
dc.subjectEpigallocatechin-3-gallatees
dc.subjectAntioxidant natural productses
dc.subject.otherCDU::5 - Ciencias puras y naturales::57 - Biología::577 - Bioquímica. Biología molecular. Biofísicaes
dc.titleSynthesis and Biological Activity of a 3,4,5-Trimethoxybenzoyl Ester Analogue of Epicatechin-3-gallatees
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
relation.isAuthorOfPublication36d7ac7e-b9a7-477c-8f7e-f03d4cc834c1
relation.isAuthorOfPublicationf702e5be-3f82-4512-b2a2-6c69a5cb98ff
relation.isAuthorOfPublication.latestForDiscovery36d7ac7e-b9a7-477c-8f7e-f03d4cc834c1
Files
Original bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
JMEDCHEM-TMECG 2008.pdf
Size:
491.06 KB
Format:
Adobe Portable Document Format
Description:
Download
License bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
license.txt
Size:
2.26 KB
Format:
Item-specific license agreed upon to submission
Description:
Download
Collections
Artículos