Publicação
Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profile
| Resumo: | The 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. |
|---|---|
| Autores principais: | Calhelha, Ricardo C. |
| Outros Autores: | Peixoto, Daniela; Vilas-Boas, Miguel; Queiroz, Maria João R.P.; Ferreira, Isabel C.F.R. |
| Assunto: | Antioxidant activity Di(hetero)arylamine EElectrochemical assays Tthieno[3,2-b]pyridine |
| Ano: | 2014 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Instituto Politécnico de Bragança |
| Idioma: | inglês |
| Origem: | Biblioteca Digital do IPB |
| _version_ | 1863851107106684928 |
|---|---|
| author | Calhelha, Ricardo C. |
| author2 | Peixoto, Daniela Vilas-Boas, Miguel Queiroz, Maria João R.P. Ferreira, Isabel C.F.R. |
| author2_role | author author author author |
| author_facet | Calhelha, Ricardo C. Peixoto, Daniela Vilas-Boas, Miguel Queiroz, Maria João R.P. Ferreira, Isabel C.F.R. |
| author_role | author |
| contributor_name_str_mv | Biblioteca Digital do IPB |
| country_str | PT |
| creators_json_str | [{\"Person.name\":\"Calhelha, Ricardo C.\",\"Person.identifier.orcid\":\"0000-0002-6801-4578\"},{\"Person.name\":\"Peixoto, Daniela\"},{\"Person.name\":\"Vilas-Boas, Miguel\",\"Person.identifier.orcid\":\"0000-0002-8665-5280\"},{\"Person.name\":\"Queiroz, Maria João R.P.\"},{\"Person.name\":\"Ferreira, Isabel C.F.R.\",\"Person.identifier.orcid\":\"0000-0003-4910-4882\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Biblioteca Digital do IPB |
| datacite.creators.creator.creatorName.fl_str_mv | Calhelha, Ricardo C. Peixoto, Daniela Vilas-Boas, Miguel Queiroz, Maria João R.P. Ferreira, Isabel C.F.R. |
| datacite.date.Accepted.fl_str_mv | 2014-01-01T00:00:00Z |
| datacite.date.available.fl_str_mv | 2014-08-14T10:24:09Z |
| datacite.date.embargoed.fl_str_mv | 2014-08-14T10:24:09Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | Antioxidant activity Di(hetero)arylamine EElectrochemical assays Tthieno[3,2-b]pyridine |
| datacite.titles.title.fl_str_mv | Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profile |
| dc.contributor.none.fl_str_mv | Biblioteca Digital do IPB |
| dc.creator.none.fl_str_mv | Calhelha, Ricardo C. Peixoto, Daniela Vilas-Boas, Miguel Queiroz, Maria João R.P. Ferreira, Isabel C.F.R. |
| dc.date.Accepted.fl_str_mv | 2014-01-01T00:00:00Z |
| dc.date.available.fl_str_mv | 2014-08-14T10:24:09Z |
| dc.date.embargoed.fl_str_mv | 2014-08-14T10:24:09Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | http://hdl.handle.net/10198/10159 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Informa Healthcare |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.subject.none.fl_str_mv | Antioxidant activity Di(hetero)arylamine EElectrochemical assays Tthieno[3,2-b]pyridine |
| dc.title.fl_str_mv | Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profile |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | The 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. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | article |
| fulltext.url.fl_str_mv | https://bibliotecadigital.ipb.pt/bitstreams/b08f24bd-39a8-431b-85aa-0fa970a2dff6/download |
| funding.funder.alternateName_str_mv | FCT FCT FCT |
| funding.funder.identifier_str_mv | http://doi.org/10.13039/501100001871 http://doi.org/10.13039/501100001871 http://doi.org/10.13039/501100001871 |
| funding.funder.name_str_mv | Fundação para a Ciência e a Tecnologia Fundação para a Ciência e a Tecnologia Fundação para a Ciência e a Tecnologia |
| funding.identifier_str_mv | PEst-OE/AGR/UI0690/2011 PTDC/QUI-QUI/111060/2009 SFRH/BPD/68344/2010 |
| funding.name_str_mv | 6817 - DCRRNI ID 5876-PPCDTI SFRH |
| funding_str_mv | PEst-OE/AGR/UI0690/2011 info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/PEst-OE%2FAGR%2FUI0690%2F2011/PT PTDC/QUI-QUI/111060/2009 info:eu-repo/grantAgreement/FCT/5876-PPCDTI/PTDC%2FQUI-QUI%2F111060%2F2009/PT SFRH/BPD/68344/2010 info:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBPD%2F68344%2F2010/PT |
| id | ipb_aea63215fc5bd88fcb3355fb7d2da2f8 |
| identifier.url.fl_str_mv | http://hdl.handle.net/10198/10159 |
| instacron_str | ipb |
| institution | Instituto Politécnico de Bragança |
| instname_str | Instituto Politécnico de Bragança |
| language | eng |
| network_acronym_str | ipb |
| network_name_str | Biblioteca Digital do IPB |
| oai_identifier_str | oai:bibliotecadigital.ipb.pt:10198/10159 |
| organization_str_mv | urn:organizationAcronym:ipb |
| person_str_mv | Calhelha, Ricardo C. Calhelha, Ricardo C. https://www.ciencia-id.pt/F313-E3CE-554E F313-E3CE-554E http://orcid.org/0000-0002-6801-4578 0000-0002-6801-4578 Peixoto, Daniela Vilas-Boas, Miguel Vilas-Boas, Miguel https://www.ciencia-id.pt/A918-C6FF-81A4 A918-C6FF-81A4 http://orcid.org/0000-0002-8665-5280 0000-0002-8665-5280 Queiroz, Maria João R.P. Ferreira, Isabel C.F.R. Ferreira, Isabel C.F.R. https://www.ciencia-id.pt/9418-CF95-9919 9418-CF95-9919 http://orcid.org/0000-0003-4910-4882 0000-0003-4910-4882 |
| publishDate | 2014 |
| publisher.none.fl_str_mv | Informa Healthcare |
| reponame_str | Biblioteca Digital do IPB |
| repository_id_str | urn:repositoryAcronym:ipb |
| service_str_mv | urn:repositoryAcronym:ipb |
| spelling | engInforma HealthcareporThe 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.application/pdfporAntioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profilePersonalCalhelha, Ricardo C.DSpacehttp://dspace.org/items/2d5d1a41-7561-4a01-871c-b4c97da35053DSpacehttp://dspace.org/items/2d5d1a41-7561-4a01-871c-b4c97da35053CalhelhaRicardo C.Ciência IDhttps://www.ciencia-id.ptF313-E3CE-554EORCIDhttp://orcid.org0000-0002-6801-4578Researcher IDhttps://www.researcherid.comJ-2172-2014Scopus Author IDhttps://www.scopus.com6507978333Peixoto, DanielaPersonalVilas-Boas, MiguelDSpacehttp://dspace.org/items/f58280c8-298b-4e4c-9f7c-4517300d3382DSpacehttp://dspace.org/items/f58280c8-298b-4e4c-9f7c-4517300d3382Vilas-BoasMiguelCiência IDhttps://www.ciencia-id.ptA918-C6FF-81A4ORCIDhttp://orcid.org0000-0002-8665-5280Researcher IDhttps://www.researcherid.comI-5949-2013Scopus Author IDhttps://www.scopus.com6602648497Queiroz, Maria João R.P.PersonalFerreira, Isabel C.F.R.DSpacehttp://dspace.org/items/bd0d1537-2e03-41fb-b27a-140af9c35db8DSpacehttp://dspace.org/items/bd0d1537-2e03-41fb-b27a-140af9c35db8FerreiraIsabel C.F.R.Ciência IDhttps://www.ciencia-id.pt9418-CF95-9919ORCIDhttp://orcid.org0000-0003-4910-4882Researcher IDhttps://www.researcherid.comE-8500-2013Scopus Author IDhttps://www.scopus.com36868826600HostingInstitutionOrganizationalBiblioteca Digital do IPBe-mailmailto:dspace@ipb.ptdspace@ipb.ptISSNIsPartOf1475-6374DOIIsPartOf10.3109/14756366.2013.7777182014-08-14T10:24:09Z20142014-01-01T00:00:00ZHandlehttp://hdl.handle.net/10198/10159http://purl.org/coar/access_right/c_abf2open accessAntioxidant activityDi(hetero)arylamineEElectrochemical assaysTthieno[3,2-b]pyridine414012 bytesFundação para a Ciência e a TecnologiaStrategic Project - UI 690 - 2011-2012info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/PEst-OE%2FAGR%2FUI0690%2F2011/PTPEst-OE/AGR/UI0690/20116817 - DCRRNI IDCrossref Funder IDhttp://doi.org/10.13039/501100001871Fundação para a Ciência e a TecnologiaNew antitumor and antiangiogenic heterocyclic compounds: synthesis, molecular modeling, screening of enzymatic inhibition and studies in tumor and endothelial cell lines with tyrosine kinase membrane receptors as targetsinfo:eu-repo/grantAgreement/FCT/5876-PPCDTI/PTDC%2FQUI-QUI%2F111060%2F2009/PTPTDC/QUI-QUI/111060/20095876-PPCDTICrossref Funder IDhttp://doi.org/10.13039/501100001871Fundação para a Ciência e a TecnologiaNew antitumor and/or anti-angiogenic heterocyclic compounds: Synthesis, molecular modelling and inhibition enzymatic assays using tyrosine kinase membrane growth factor receptorsinfo:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBPD%2F68344%2F2010/PTSFRH/BPD/68344/2010SFRHCrossref Funder IDhttp://doi.org/10.13039/501100001871literaturehttp://purl.org/coar/resource_type/c_6501journal articlehttp://purl.org/coar/access_right/c_abf2application/pdffulltexthttps://bibliotecadigital.ipb.pt/bitstreams/b08f24bd-39a8-431b-85aa-0fa970a2dff6/downloadJournal Of Enzyme Inhibition and Medicinal Chemistry29311316 |
| spellingShingle | Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profile Calhelha, Ricardo C. Antioxidant activity Di(hetero)arylamine EElectrochemical assays Tthieno[3,2-b]pyridine |
| subject.fl_str_mv | Antioxidant activity Di(hetero)arylamine EElectrochemical assays Tthieno[3,2-b]pyridine |
| title | Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profile |
| title_full | Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profile |
| title_fullStr | Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profile |
| title_full_unstemmed | Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profile |
| title_short | Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profile |
| title_sort | Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profile |
| topic | Antioxidant activity Di(hetero)arylamine EElectrochemical assays Tthieno[3,2-b]pyridine |
| topic_facet | Antioxidant activity Di(hetero)arylamine EElectrochemical assays Tthieno[3,2-b]pyridine |
| url | http://hdl.handle.net/10198/10159 |
| visible | 1 |
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