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Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profile

2014Journal article Open access
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dc.contributor.authorCalhelha, Ricardo C.
dc.contributor.authorPeixoto, Daniela
dc.contributor.authorVilas-Boas, Miguel
dc.contributor.authorQueiroz, Maria João R.P.
dc.contributor.authorFerreira, Isabel C.F.R.
dc.date.accessioned2014-08-14T10:24:09Z
dc.date.available2014-08-14T10:24:09Z
dc.date.issued2014
dc.description.abstractThe antioxidant activity of the aminodi(hetero)arylamines, prepared by C-N coupling of the methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate with bromonitrobenzenes and further reduction of the obtained nitro compounds, was evaluated by chemical, biochemical and electrochemical assays. The aminodi(hetero) arylamine with the amino group ortho to the NH and a methoxy group in para, was the most efficient in radical scavenging activity (RSA, 63 mu M) and reducing power (RP, 33 mu M), while the aminodiarylamine with the amino group in para to the NH, gave the best results in beta-carotene-linoleate system (41 mu M) and inhibition of formation of thiobarbituric acid reactive substances in porcine brain cells homogenates (7 mu M), with EC50 values even lower than those obtained for the standard trolox. This diarylamine also presented the lowest oxidation potential, lower than the one of trolox, and the highest antioxidant power in the electrochemical assays. The para substitution with an amino group enables higher antioxidant potential.por
dc.description.sponsorshipFCT and FEDER (European Fund for Regional Development)-COMPETE/QREN/EU for financial support through the research unities PEst-C/QUI/UI686/2011 and PEst-OE/ AGR/UI0690/2011, the research project PTDC/QUI-QUI/111060/2009 and the post-Doctoral grant attributed to R.C.C. (SFRH/BPD/68344/ 2010).por
dc.identifier.citationCalhelha, Ricardo C.; Peixoto, Daniela; Vilas-Boas, Miguel; Queiroz, Maria-João R.P.; Ferreira, Isabel C.F.R. (2014). Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profile. Journal of Enzyme Inhibition and Medicinal Chemistry. ISSN 1475-6374. 29:3, p. 311-316por
dc.identifier.doi10.3109/14756366.2013.777718
dc.identifier.issn1475-6374
dc.identifier.urihttp://hdl.handle.net/10198/10159
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherInforma Healthcarepor
dc.relationPEst-C/QUI/UI686/2011
dc.relationStrategic Project - UI 690 - 2011-2012
dc.relationNEW ANTITUMOR AND/OR ANTI-ANGIOGENIC HETEROCYCLIC COMPOUNDS: SYNTHESIS, MOLECULAR MODELLING AND INHIBITION ENZYMATIC ASSAYS USING TYROSINE KINASE MEMBRANE GROWTH FACTOR RECEPTORS
dc.subjectAntioxidant activitypor
dc.subjectDi(hetero)arylaminepor
dc.subjectEElectrochemical assayspor
dc.subjectTthieno[3,2-b]pyridinepor
dc.titleAntioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profilepor
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleStrategic Project - UI 690 - 2011-2012
oaire.awardTitleNEW ANTITUMOR AND/OR ANTI-ANGIOGENIC HETEROCYCLIC COMPOUNDS: SYNTHESIS, MOLECULAR MODELLING AND INHIBITION ENZYMATIC ASSAYS USING TYROSINE KINASE MEMBRANE GROWTH FACTOR RECEPTORS
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/PEst-OE%2FAGR%2FUI0690%2F2011/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/5876-PPCDTI/PTDC%2FQUI-QUI%2F111060%2F2009/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/FARH/SFRH%2FBPD%2F68344%2F2010/PT
oaire.citation.endPage316por
oaire.citation.startPage311por
oaire.citation.titleJournal Of Enzyme Inhibition and Medicinal Chemistrypor
oaire.citation.volume29por
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream5876-PPCDTI
oaire.fundingStreamFARH
person.familyNameCalhelha
person.familyNameVilas-Boas
person.familyNameFerreira
person.givenNameRicardo C.
person.givenNameMiguel
person.givenNameIsabel C.F.R.
person.identifier1693134
person.identifier144781
person.identifier.ciencia-idF313-E3CE-554E
person.identifier.ciencia-idA918-C6FF-81A4
person.identifier.ciencia-id9418-CF95-9919
person.identifier.orcid0000-0002-6801-4578
person.identifier.orcid0000-0002-8665-5280
person.identifier.orcid0000-0003-4910-4882
person.identifier.ridJ-2172-2014
person.identifier.ridI-5949-2013
person.identifier.ridE-8500-2013
person.identifier.scopus-author-id6507978333
person.identifier.scopus-author-id6602648497
person.identifier.scopus-author-id36868826600
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccesspor
rcaap.typearticlepor
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