Improvement of Pro-Oxidant Capacity of Protocatechuic Acid by Esterification

Página do item simplificado
dc.contributor.authorZeraik, Maria Luiza [UNESP]
dc.contributor.authorPetronio, Maicon S. [UNESP]
dc.contributor.authorCoelho, Dyovani
dc.contributor.authorRegasini, Luis Octavio [UNESP]
dc.contributor.authorSilva, Dulce Helena Siqueira [UNESP]
dc.contributor.authorFonseca, Luiz Marcos da [UNESP]
dc.contributor.authorMachado, Sergio A. S.
dc.contributor.authorBolzani, Vanderlan da Silva [UNESP]
dc.contributor.authorXimenes, Valdecir F. [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniversidade de São Paulo (USP)
dc.date.accessioned2015-03-18T15:56:04Z
dc.date.available2015-03-18T15:56:04Z
dc.date.issued2014-10-23
dc.description.abstractPro-oxidant effects of phenolic compounds are usually correlated to the one-electron redox potential of the phenoxyl radicals. Here we demonstrated that, besides their oxidizability, hydrophobicity can also be a decisive factor. We found that esterification of protocatechuic acid (P0) provoked a profound influence in its pro-oxidant capacity. The esters bearing alkyl chains containing two (P2), four (P4) and seven (P7) carbons, but not the acid precursor (P0), were able to exacerbate the oxidation of trolox, alpha-tocopherol and rifampicin. This effect was also dependent on the catechol moiety, since neither gallic acid nor butyl gallate showed any pro-oxidant effects. A comparison was also made with apocynin, which is well-characterized regarding its pro-oxidant properties. P7 was more efficient than apocynin regarding co-oxidation of trolox. However, P7 was not able to co-oxidize glutathione and NADH, which are targets of the apocynin radical. A correlation was found between pro-oxidant capacity and the stability of the radicals, as suggested by the intensity of the peak current in the differential pulse voltammetry experiments. In conclusion, taking into account that hydroquinone and related moieties are frequently found in biomolecules and quinone-based chemotherapeutics, our demonstration that esters of protocatechuic acid are specific and potent co-catalysts in their oxidations may be very relevant as a pathway to exacerbate redox cycling reactions, which are usually involved in their biological and pharmacological mechanisms of action.en
dc.description.affiliationSao Paulo State Univ, UNESP, Fac Sci, Dept Chem, Sao Paulo, Brazil
dc.description.affiliationSao Paulo State Univ, UNESP, Nuclei Bioassays Ecophysiol & Biosynth Nat Prod N, Dept Organ Chem,Inst Chem, Sao Paulo, Brazil
dc.description.affiliationSao Paulo State Univ, UNESP, Sch Pharmaceut Sci, Dept Clin Anal, Sao Paulo, Brazil
dc.description.affiliationUniv Sao Paulo, Inst Chem Sao Carlos, Sao Carlos, SP, Brazil
dc.description.affiliationUnespSao Paulo State Univ, UNESP, Fac Sci, Dept Chem, Sao Paulo, Brazil
dc.description.affiliationUnespSao Paulo State Univ, UNESP, Nuclei Bioassays Ecophysiol & Biosynth Nat Prod N, Dept Organ Chem,Inst Chem, Sao Paulo, Brazil
dc.description.affiliationUnespSao Paulo State Univ, UNESP, Sch Pharmaceut Sci, Dept Clin Anal, Sao Paulo, Brazil
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.description.sponsorshipCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.description.sponsorshipIdFAPESP: 13/08784-0
dc.description.sponsorshipIdFAPESP: 010/52327-5
dc.description.sponsorshipIdFAPESP: 11/03017-6
dc.description.sponsorshipIdFAPESP: 13/07600-3
dc.format.extent9
dc.identifierhttp://dx.doi.org/10.1371/journal.pone.0110277
dc.identifier.citationPlos One. San Francisco: Public Library Science, v. 9, n. 10, 9 p., 2014.
dc.identifier.doi10.1371/journal.pone.0110277
dc.identifier.fileWOS000343662800025.pdf
dc.identifier.issn1932-6203
dc.identifier.lattes4702004904231248
dc.identifier.lattes4484083685251673
dc.identifier.orcid0000-0002-1516-7765
dc.identifier.urihttp://hdl.handle.net/11449/117414
dc.identifier.wosWOS:000343662800025
dc.language.isoeng
dc.publisherPublic Library Science
dc.relation.ispartofPlos One
dc.relation.ispartofjcr2.766
dc.relation.ispartofsjr1,164
dc.rights.accessRightsAcesso aberto
dc.sourceWeb of Science
dc.titleImprovement of Pro-Oxidant Capacity of Protocatechuic Acid by Esterificationen
dc.typeArtigo
dcterms.rightsHolderPublic Library Science
unesp.author.lattes4702004904231248[5]
unesp.author.lattes4484083685251673
unesp.author.orcid0000-0002-1516-7765[5]
unesp.campusUniversidade Estadual Paulista (Unesp), Instituto de Química, Araraquarapt
unesp.campusUniversidade Estadual Paulista (Unesp), Faculdade de Ciências Farmacêuticas, Araraquarapt

Arquivos

Pacote Original
Agora exibindo 1 - 1 de 1
Imagem de Miniatura
Nome:
WOS000343662800025.pdf
Tamanho:
1.08 MB
Formato:
Adobe Portable Document Format
Baixar

Coleções

Artigos - Química Orgânica - IQ
Artigos - Análises Clínicas - FCFAR