Taurine bromamine: Reactivity of an endogenous and exogenous anti-inflammatory and antimicrobial amino acid derivative

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dc.contributor.authorBertozo, Luiza De Carvalho [UNESP]
dc.contributor.authorMorgon, Nelson Henrique
dc.contributor.authorDe Souza, Aguinaldo Robinson [UNESP]
dc.contributor.authorXimenes, Valdecir Farias [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniversidade Estadual de Campinas (UNICAMP)
dc.date.accessioned2018-12-11T17:31:25Z
dc.date.available2018-12-11T17:31:25Z
dc.date.issued2016-04-21
dc.description.abstractTaurine bromamine (Tau-NHBr) is produced by the reaction between hypobromous acid (HOBr) and the amino acid taurine. There are increasing number of applications of Tau-NHBr as an anti-inflammatory and microbicidal drug for topical usage. Here, we performed a comprehensive study of the chemical reactivity of Tau-NHBr with endogenous and non-endogenous compounds. Tau-NHBr reactivity was compared with HOBr, hypochlorous acid (HOCl) and taurine chloramine (Tau-NHCl). The second-order rate constants (k2) for the reactions between Tau-NHBr and tryptophan (7.7 x 102 M-1s-1), melatonin (7.3 × 103 M-1s-1), serotonin (2.9 × 103 M-1s-1), dansylglycine (9.5 × 101 M-1s-1), tetramethylbenzidine (6.4 × 102 M-1s-1) and H2O2 (3.9 x M-1s-1) were obtained. Tau-NHBr demonstrated the following selectivity regarding its reactivity with free amino acids: tryptophan > cysteine ~ methionine > tyrosine. The reactivity of Tau-NHBr was strongly affected by the pH of the medium (for instance with dansylglycine: pH 5.0,1.1 × 104 M-1s-1, pH 7.0, 9.5 × 10 M-1s-1 and pH 9.0, 1.7 × 10 M-1s-1), a property that is related to the formation of the dibromamine form at acidic pH (Tau-NBr2). The formation of singlet oxygen was observed in the reaction between Tau-NHBr and H2O2. Tau-NHBr was also able to react with linoleic acid, but with low efficiency compared with HOBr and HOCl. Compared with HOBr, Tau-NHBr was not able to react with nucleosides. In conclusion, the following reactivity sequence was established: HOBr > HOCl > Tau-NHBr > Tau-NHCl. These findings can be very helpful for researchers interested in biological applications of taurine haloamines.en
dc.description.affiliationDepartment of Chemistry Faculty of Sciences São Paulo State University (UNESP)
dc.description.affiliationDepartment of Chemistry Institute of Chemistry Campinas State University (UNICAMP)
dc.description.affiliationUnespDepartment of Chemistry Faculty of Sciences São Paulo State University (UNESP)
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.sponsorshipIdFAPESP: 2013/08784-0
dc.description.sponsorshipIdFAPESP: 2105/08267-1
dc.description.sponsorshipIdCNPq: 440503/2014-0
dc.identifierhttp://dx.doi.org/10.3390/biom6020023
dc.identifier.citationBiomolecules, v. 6, n. 2, 2016.
dc.identifier.doi10.3390/biom6020023
dc.identifier.file2-s2.0-85012036965.pdf
dc.identifier.issn2218-273X
dc.identifier.scopus2-s2.0-85012036965
dc.identifier.urihttp://hdl.handle.net/11449/178633
dc.language.isoeng
dc.relation.ispartofBiomolecules
dc.rights.accessRightsAcesso aberto
dc.sourceScopus
dc.subjectMelatonin
dc.subjectNucleosides
dc.subjectSerotonin
dc.subjectSinglet oxygen
dc.subjectTaurine bromamine
dc.subjectTryptophan
dc.titleTaurine bromamine: Reactivity of an endogenous and exogenous anti-inflammatory and antimicrobial amino acid derivativeen
dc.typeArtigo
unesp.departmentQuímica - FCpt

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