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Importance of phenols structure on their activity as antinitrosating agents: a kinetic study

dc.contributor.authorMoreira, José
dc.contributor.authorPessêgo, Márcia
dc.contributor.authorCosta, Ana M. Rosa da
dc.date.accessioned2013-12-09T17:23:14Z
dc.date.available2013-12-09T17:23:14Z
dc.date.issued2011
dc.date.updated2013-12-04T18:08:19Z
dc.description.abstractObjective : Nitrosative deamination of DNA bases induced by reaction with reactive nitrogen species (RNS) has been pointed out as a probable cause of mutagenesis. (Poly)phenols, present in many food items from the Mediterranean diet, are believed to possess antinitrosating properties due to their RNS scavenging ability, which seems to be related to their structure. It has been suggested that phenolic compounds will react with the above-mentioned species more rapidly than most amino compounds, thus preventing direct nitrosation of the DNA bases and their transnitrosation from endogenous N-nitroso compounds, or most likely from the transient N-nitrosocompounds formed in vivo. Materials and Methods : In order to prove that assumption, a kinetic study of the nitroso group transfer from a N-methyl-N-nitrosobenzenesulfonamide (N-methyl-N-nitroso-4-methylbenzenesulfonamide, MeNMBS) to the DNA bases bearing an amine group and to a series of phenols was carried out. In the transnitrosation of phenols, the formation of nitrosophenol was monitored by Ultraviolet (UV) / Visible spectroscopy, and in the reactions of the DNA bases, the consumption of MeNMBS was followed by high performance liquid chromatography (HPLC). Results : The results obtained point to the transnitrosation of DNA bases being negligible, as well as that of phenols bearing electron-withdrawing groups. Phenols with methoxy substituents in positions 2, 4, and / or 6, although they seemed to react, did not afford the expected product. Phenols with electron-releasing substituents, unless these blocked the oxygen atom, reacted with our model compound at an appreciable rate. O-nitrosation of the phenolate ion followed by rearrangement of the C-nitrosophenol seemed to be involved. Conclusion : This study provided evidence that the above compounds might actually act as antinitrosating agents in vivo.por
dc.identifier.citationMoreira, José A.; Pessêgo, Márcia; Rosa da Costa, Ana M.Importance of phenols structure on their activity as antinitrosating agents: A kinetic study, Journal of Pharmacy and Bioallied Sciences, 3, 1, 128-34, 2011.por
dc.identifier.doihttp://dx.doi.org/10.4103/0975-7406.76491
dc.identifier.issn0975-7406
dc.identifier.otherAUT: JMO01545; AMC01695;
dc.identifier.urihttp://hdl.handle.net/10400.1/3234
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherOrganization of Pharmaceutical Unity with BioAllied Sciencespor
dc.relation.publisherversionhttp://www.jpbsonline.org/text.asp?2011/3/1/128/76491por
dc.subjectAntinitrosating actionpor
dc.subjectDNA basespor
dc.subjectKineticspor
dc.subjectN-methyl-N-nitrosobenzenesulfonamidespor
dc.subjectPhenolspor
dc.subjectTransnitrosationpor
dc.titleImportance of phenols structure on their activity as antinitrosating agents: a kinetic studypor
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage134por
oaire.citation.startPage128por
oaire.citation.titleJournal of Pharmacy and Bioallied Sciencespor
oaire.citation.volume3por
person.familyNameMoreira
person.familyNameRosa da Costa
person.givenNameJosé
person.givenNameAna M
person.identifier305029
person.identifier.ciencia-idDC11-4E1F-F13F
person.identifier.ciencia-idA418-A85E-5DB1
person.identifier.orcid0000-0001-8481-3436
person.identifier.orcid0000-0003-0225-9537
person.identifier.ridF-3807-2010
person.identifier.ridE-2165-2012
person.identifier.scopus-author-id7201506886
person.identifier.scopus-author-id53986075100
rcaap.rightsopenAccesspor
rcaap.typearticlepor
relation.isAuthorOfPublication644799ac-df06-4840-9f12-52c5b3ff0a76
relation.isAuthorOfPublication0ca8c16f-6881-4662-bafc-cc51c5ce8d88
relation.isAuthorOfPublication.latestForDiscovery0ca8c16f-6881-4662-bafc-cc51c5ce8d88

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