Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profile
Autor(a) principal: | |
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Data de Publicação: | 2014 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10198/10159 |
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. |
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Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profileAntioxidant activityDi(hetero)arylamineEElectrochemical assaysTthieno[3,2-b]pyridineThe 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.FCT 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).Informa HealthcareBiblioteca Digital do IPBCalhelha, Ricardo C.Peixoto, DanielaVilas-Boas, MiguelQueiroz, Maria João R.P.Ferreira, Isabel C.F.R.2014-08-14T10:24:09Z20142014-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10198/10159engCalhelha, 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. 311-3161475-637410.3109/14756366.2013.777718info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-01-16T12:12:15ZPortal AgregadorONG |
dc.title.none.fl_str_mv |
Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profile |
title |
Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profile |
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 |
title_short |
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_sort |
Antioxidant activity of aminodiarylamines in the thieno[3,2-b]pyridine series: radical scavenging activity, lipid peroxidation inhibition and redox profile |
author |
Calhelha, Ricardo C. |
author_facet |
Calhelha, Ricardo C. Peixoto, Daniela Vilas-Boas, Miguel Queiroz, Maria João R.P. Ferreira, Isabel C.F.R. |
author_role |
author |
author2 |
Peixoto, Daniela Vilas-Boas, Miguel Queiroz, Maria João R.P. Ferreira, Isabel C.F.R. |
author2_role |
author author author author |
dc.contributor.none.fl_str_mv |
Biblioteca Digital do IPB |
dc.contributor.author.fl_str_mv |
Calhelha, Ricardo C. Peixoto, Daniela Vilas-Boas, Miguel Queiroz, Maria João R.P. Ferreira, Isabel C.F.R. |
dc.subject.por.fl_str_mv |
Antioxidant activity Di(hetero)arylamine EElectrochemical assays Tthieno[3,2-b]pyridine |
topic |
Antioxidant activity Di(hetero)arylamine EElectrochemical assays Tthieno[3,2-b]pyridine |
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. |
publishDate |
2014 |
dc.date.none.fl_str_mv |
2014-08-14T10:24:09Z 2014 2014-01-01T00:00:00Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10198/10159 |
url |
http://hdl.handle.net/10198/10159 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Calhelha, 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. 311-316 1475-6374 10.3109/14756366.2013.777718 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Informa Healthcare |
publisher.none.fl_str_mv |
Informa Healthcare |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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1777301872136159232 |