Hypobromous Acid, A Powerful Endogenous Electrophile: Experimental And Theoretical Studies.

dc.creatorXimenes, Valdecir Farias
dc.creatorMorgon, Nelson Henrique
dc.creatorde Souza, Aguinaldo Robinson
dc.date2015-May
dc.date2015-11-27T13:46:26Z
dc.date2015-11-27T13:46:26Z
dc.date.accessioned2018-03-29T01:23:54Z
dc.date.available2018-03-29T01:23:54Z
dc.identifierJournal Of Inorganic Biochemistry. v. 146, p. 61-8, 2015-May.
dc.identifier1873-3344
dc.identifier10.1016/j.jinorgbio.2015.02.014
dc.identifierhttp://www.ncbi.nlm.nih.gov/pubmed/25771434
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/202221
dc.identifier25771434
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1302454
dc.descriptionHypobromous acid (HOBr) is an inorganic acid produced by the oxidation of the bromide anion (Br(-)). The blood plasma level of Br(-) is more than 1,000-fold lower than that of chloride anion (Cl(-)). Consequently, the endogenous production of HOBr is also lower compared to hypochlorous acid (HOCl). Nevertheless, there is much evidence of the deleterious effects of HOBr. From these data, we hypothesized that the reactivity of HOBr could be better associated with its electrophilic strength. Our hypothesis was confirmed, since HOBr was significantly more reactive than HOCl when the oxidability of the studied compounds was not relevant. For instance: anisole (HOBr, k2=2.3×10(2)M(-1)s(-1), HOCl non-reactive); dansylglycine (HOBr, k2=7.3×10(6)M(-1)s(-1), HOCl, 5.2×10(2)M(-1)s(-1)); salicylic acid (HOBr, k2=4.0×10(4)M(-1)s(-1), non-reactive); 3-hydroxybenzoic acid (HOBr, k2=5.9×10(4)M(-1)s(-1), HOCl, k2=1.1×10(1)M(-1)s(-1)); uridine (HOBr, k2=1.3×10(3)M(-1)s(-1), HOCl non-reactive). The compounds 4-bromoanisole and 5-bromouridine were identified as the products of the reactions between HOBr and anisole or uridine, respectively, i.e. typical products of electrophilic substitutions. Together, these results show that, rather than an oxidant, HOBr is a powerful electrophilic reactant. This chemical property was theoretically confirmed by measuring the positive Mulliken and ChelpG charges upon bromine and chlorine. In conclusion, the high electrophilicity of HOBr could be behind its well-established deleterious effects. We propose that HOBr is the most powerful endogenous electrophile.
dc.description146
dc.description61-8
dc.languageeng
dc.relationJournal Of Inorganic Biochemistry
dc.relationJ. Inorg. Biochem.
dc.rightsfechado
dc.rightsCopyright © 2015 Elsevier Inc. All rights reserved.
dc.sourcePubMed
dc.subjectHypobromous Acid
dc.subjectHypochlorous Acid
dc.subjectMyeloperoxidase
dc.subjectReactive Electrophilic Species
dc.subjectReactive Oxygen Species
dc.titleHypobromous Acid, A Powerful Endogenous Electrophile: Experimental And Theoretical Studies.
dc.typeArtículos de revistas


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