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dc.contributor.authorde Faria, C. M. Q. G. [UNESP]
dc.contributor.authorNazare, A. C. [UNESP]
dc.contributor.authorPetronio, M. S. [UNESP]
dc.contributor.authorParacatu, L. C. [UNESP]
dc.contributor.authorZeraik, M. L. [UNESP]
dc.contributor.authorRegasini, L. O. [UNESP]
dc.contributor.authorSilva, Dulce Helena Siqueira [UNESP]
dc.contributor.authorda Fonseca, L. M. [UNESP]
dc.contributor.authorXimenes, V. F. [UNESP]
dc.date.accessioned2014-05-20T13:26:57Z
dc.date.available2014-05-20T13:26:57Z
dc.date.issued2012-10-01
dc.identifierhttp://dx.doi.org/10.2174/092986712803341557
dc.identifier.citationCurrent Medicinal Chemistry. Sharjah: Bentham Science Publ Ltd, v. 19, n. 28, p. 4885-4893, 2012.
dc.identifier.issn0929-8673
dc.identifier.urihttp://hdl.handle.net/11449/8766
dc.description.abstractThis study presents the increased efficiency of NADPH oxidase inhibition produced by esterification of protocatechuic acid (P0). Alkyl esters bearing chain lengths of 4 (P4), 7 (P7) and 10 (P10) carbons were synthesized and their oxidation potential, hydrophobicity, antiradical activity, inhibition of superoxide anion (O-2(center dot-)), and the abilities to affect hypochlorous acid (HOCl) production by leukocytes and inhibit myeloperoxidase (MPO) chlorinating activity were studied. The increased hydrophobicity (logP, 0.81-4.82) of the esters was not correlated with a significant alteration in their oxidation potential (0.222-0.298 V). However, except for P10, the esters were similar to 2-fold more effective than the acid precursor for the scavenging of DPPH and peroxyl radicals. The esters were strong inhibitors of O2 released by activated neutrophils (PMNs) and peripheral blood mononuclear cells (PBMCs). A correlation was found between the carbon chain length and the relative inhibitory potency. P7, the most active ester, was similar to 10-fold more efficient as NADPH oxidase inhibitor than apocynin. The esters strongly inhibited the release of HOCl by PMNs, which was a consequence of the inhibition of NADPH oxidase activity in these cells. In conclusion, as effective inhibitors of NADPH oxidase, the esters of protocatechuic acid are promising drugs for treatment of chronic inflammatory diseases. Moreover, this is the first demonstration that, besides the redox active moiety, the hydrophobicity can also be a determinant factor for the design of NADPH oxidase inhibitors.en
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.format.extent4885-4893
dc.language.isoeng
dc.publisherBentham Science Publ Ltd
dc.relation.ispartofCurrent Medicinal Chemistry
dc.sourceWeb of Science
dc.titleProtocatechuic Acid Alkyl Esters: Hydrophobicity As a Determinant Factor for Inhibition of NADPH Oxidaseen
dc.typeResenha
dcterms.licensehttp://www.benthamscience.com/permission.php
dcterms.rightsHolderBentham Science Publ Ltd
dc.contributor.institutionUniversidade Estadual Paulista (UNESP)
dc.description.affiliationSão Paulo State Univ UNESP, Dept Chem, Fac Sci, BR-17033360 São Paulo, Brazil
dc.description.affiliationSão Paulo State Univ UNESP, Dept Clin Anal, Sch Pharmaceut Sci, BR-14801902 São Paulo, Brazil
dc.description.affiliationSão Paulo State Univ UNESP, Dept Organ Chem, Nuclei Bioassays Ecophysiol & Biosynthesis Nat Pr, Inst Chem, BR-14800900 São Paulo, Brazil
dc.description.affiliationUnespSão Paulo State Univ UNESP, Dept Chem, Fac Sci, BR-17033360 São Paulo, Brazil
dc.description.affiliationUnespSão Paulo State Univ UNESP, Dept Clin Anal, Sch Pharmaceut Sci, BR-14801902 São Paulo, Brazil
dc.description.affiliationUnespSão Paulo State Univ UNESP, Dept Organ Chem, Nuclei Bioassays Ecophysiol & Biosynthesis Nat Pr, Inst Chem, BR-14800900 São Paulo, Brazil
dc.identifier.doi10.2174/092986712803341557
dc.identifier.wosWOS:000309745800016
dc.rights.accessRightsAcesso restrito
unesp.campusUniversidade Estadual Paulista (UNESP), Instituto de Química, Araraquarapt
unesp.campusUniversidade Estadual Paulista (UNESP), Faculdade de Ciências Farmacêuticas, Araraquarapt
dc.identifier.lattes4702004904231248
dc.identifier.orcid0000-0002-1516-7765
unesp.author.lattes4702004904231248[7]
unesp.author.orcid0000-0002-1516-7765[7]
dc.relation.ispartofjcr3.469
dc.relation.ispartofsjr1,015
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