Horseradish peroxidase-catalyzed oxidation of rifampicin: Reaction rate enhancement by co-oxidation with anti-inflammatory drugs

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dc.contributor.authorDos Santos, Fernanda de Jesus Notário [UNESP]
dc.contributor.authorXimenes, Valdecir Farias [UNESP]
dc.contributor.authorDa Fonseca, Luiz Marcos [UNESP]
dc.contributor.authorDe Faria Oliveira, Olga Maria Mascarenhas [UNESP]
dc.contributor.authorBrunetti, Iguatemy Lourenço [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.date.accessioned2014-05-27T11:21:38Z
dc.date.available2014-05-27T11:21:38Z
dc.date.issued2005-10-01
dc.description.abstractThe tuberculostatic drug rifampicin has been described as a scavenger of reactive species. Additionally, the recent demonstration that oral therapy with a complex of rifampicin and horseradish peroxidase (HRP) was more effective than rifampicin alone, in an animal model of experimental leprosy, suggested the importance of redox reactions involving rifampicin and their relevance to the mechanism of action. Hence, we studied the oxidation of rifampicin catalyzed by HRP, since this enzyme may represent the prototype of peroxidation-mediated reactions. We found that the antibiotic is efficiently oxidized and that rifampicin-quinone is the product, in a reaction dependent on both HRP and hydrogen peroxide. The steady-state kinetic constants Km app (101±23 mmol/l), Vmax app (0.78±0.09 μmol/l·s-1) and kcat (5.1±0.6 s-1) were measured (n=4). The reaction rate was increased by the addition of co-substrates such as tetramethylbenzidine, salicylic acid, 5-aminosalicylic acid and paracetamol. This effect was explained by invoking an electron-transfer mechanism by which these drugs acted as mediators of rifampicin oxidation. We suggested that this drug interaction might be important at the inflammatory site. © 2005 Pharmaceutical Society of Japan.en
dc.description.affiliationDepartment of Clinical Analysis Faculty of Pharmaceutical Sciences UNESP- São Paulo State University, Araraquara, 14801-902, SP
dc.description.affiliationDepartment of Biochemistry and Chemistry Technology Institute of Chemistry UNESP- São Paulo State University, Araraquara, 14801-902, SP
dc.description.affiliationUnespDepartment of Clinical Analysis Faculty of Pharmaceutical Sciences UNESP- São Paulo State University, Araraquara, 14801-902, SP
dc.description.affiliationUnespDepartment of Biochemistry and Chemistry Technology Institute of Chemistry UNESP- São Paulo State University, Araraquara, 14801-902, SP
dc.format.extent1822-1826
dc.identifierhttp://dx.doi.org/10.1248/bpb.28.1822
dc.identifier.citationBiological and Pharmaceutical Bulletin, v. 28, n. 10, p. 1822-1826, 2005.
dc.identifier.doi10.1248/bpb.28.1822
dc.identifier.fileWOS000232680800002.pdf
dc.identifier.issn0918-6158
dc.identifier.issn1347-5215
dc.identifier.scopus2-s2.0-26444560869
dc.identifier.urihttp://hdl.handle.net/11449/68428
dc.identifier.wosWOS:000232680800002
dc.language.isoeng
dc.relation.ispartofBiological and Pharmaceutical Bulletin
dc.relation.ispartofjcr1.694
dc.relation.ispartofsjr0,626
dc.relation.ispartofsjr0,626
dc.rights.accessRightsAcesso aberto
dc.sourceScopus
dc.subjectHorseradish peroxidase
dc.subjectParacetamol
dc.subjectRifampicin
dc.subjectRifampicin-quinone
dc.subjectTuberculosis
dc.subjectantiinflammatory agent
dc.subjecthorseradish peroxidase
dc.subjecthydrogen peroxide
dc.subjectmesalazine
dc.subjectparacetamol
dc.subjectquinone derivative
dc.subjectrifampicin
dc.subjectsalicylic acid
dc.subjecttetramethylbenzidine
dc.subjectcatalysis
dc.subjectchemical reaction
dc.subjectdrug oxidation
dc.subjectelectron transport
dc.subjectperoxidation
dc.subjectsteady state
dc.subjectAnimals
dc.subjectAnti-Inflammatory Agents
dc.subjectAntitubercular Agents
dc.subjectCatalysis
dc.subjectHorseradish Peroxidase
dc.subjectOxidation-Reduction
dc.subjectRifampin
dc.titleHorseradish peroxidase-catalyzed oxidation of rifampicin: Reaction rate enhancement by co-oxidation with anti-inflammatory drugsen
dc.typeArtigo
dcterms.licensehttps://www.jstage.jst.go.jp/pub/html/AY04S120_en.html
unesp.campusUniversidade Estadual Paulista (Unesp), Instituto de Química, Araraquarapt
unesp.campusUniversidade Estadual Paulista (Unesp), Faculdade de Ciências Farmacêuticas, Araraquarapt
unesp.departmentAnálises Clínicas - FCFpt

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