Influence of the structure on the antioxidant activity of tetradentate schiff bases and their copper(II) complexes: possible mechanisms
Autor(a) principal: | |
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Data de Publicação: | 2013 |
Outros Autores: | , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000800013 |
Resumo: | The influence of the structure on the antioxidant activity of a series of Schiff bases and their copper(II) complexes as well as possible mechanisms of antioxidant activity were investigated. Schiff bases are derived from the condensation of ethane-1,2-diamine or propane-1,2-diamine and pentane-2,4-dione and/or 1-phenylbutane-1,3-dione. The corresponding complexes were synthesized. The antioxidant activity in vitro, determined using reversed-phase thin layer chromatography assay (RP TLC) based on the reaction with 2,2'-diphenyl-1-picrylhydrazyl, was expressed as Trolox equivalent antioxidant capacity (TEAC). The influence of the structure was observed on the basis of interpretable and informative descriptors calculated by hybrid density functional theory (DFT) methods. Structural features responsible for the antioxidant activity of the investigated compounds were discussed. Copper(II) complexes showed a significantly higher antioxidant activity than their corresponding ligands. Calculated quantum-chemical descriptors gave an insight to the reaction mechanism of the scavenging/antioxidant activity of tetradentate Schiff bases and their copper(II) complexes and two different reaction mechanisms were proposed. |
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Influence of the structure on the antioxidant activity of tetradentate schiff bases and their copper(II) complexes: possible mechanismsantioxidant activityantioxidant mechanismSchiff basecopper(II) complexesDFTThe influence of the structure on the antioxidant activity of a series of Schiff bases and their copper(II) complexes as well as possible mechanisms of antioxidant activity were investigated. Schiff bases are derived from the condensation of ethane-1,2-diamine or propane-1,2-diamine and pentane-2,4-dione and/or 1-phenylbutane-1,3-dione. The corresponding complexes were synthesized. The antioxidant activity in vitro, determined using reversed-phase thin layer chromatography assay (RP TLC) based on the reaction with 2,2'-diphenyl-1-picrylhydrazyl, was expressed as Trolox equivalent antioxidant capacity (TEAC). The influence of the structure was observed on the basis of interpretable and informative descriptors calculated by hybrid density functional theory (DFT) methods. Structural features responsible for the antioxidant activity of the investigated compounds were discussed. Copper(II) complexes showed a significantly higher antioxidant activity than their corresponding ligands. Calculated quantum-chemical descriptors gave an insight to the reaction mechanism of the scavenging/antioxidant activity of tetradentate Schiff bases and their copper(II) complexes and two different reaction mechanisms were proposed.Sociedade Brasileira de Química2013-08-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000800013Journal of the Brazilian Chemical Society v.24 n.8 2013reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20130167info:eu-repo/semantics/openAccessAburas,Najat M.Stevanovic,Nikola R.Milcic,Milos K.Lolic,Aleksandar D.Natic,Maja M.Tesic,Zivoslav Lj.Baosic,Rada M.eng2015-07-21T00:00:00Zoai:scielo:S0103-50532013000800013Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2015-07-21T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Influence of the structure on the antioxidant activity of tetradentate schiff bases and their copper(II) complexes: possible mechanisms |
title |
Influence of the structure on the antioxidant activity of tetradentate schiff bases and their copper(II) complexes: possible mechanisms |
spellingShingle |
Influence of the structure on the antioxidant activity of tetradentate schiff bases and their copper(II) complexes: possible mechanisms Aburas,Najat M. antioxidant activity antioxidant mechanism Schiff base copper(II) complexes DFT |
title_short |
Influence of the structure on the antioxidant activity of tetradentate schiff bases and their copper(II) complexes: possible mechanisms |
title_full |
Influence of the structure on the antioxidant activity of tetradentate schiff bases and their copper(II) complexes: possible mechanisms |
title_fullStr |
Influence of the structure on the antioxidant activity of tetradentate schiff bases and their copper(II) complexes: possible mechanisms |
title_full_unstemmed |
Influence of the structure on the antioxidant activity of tetradentate schiff bases and their copper(II) complexes: possible mechanisms |
title_sort |
Influence of the structure on the antioxidant activity of tetradentate schiff bases and their copper(II) complexes: possible mechanisms |
author |
Aburas,Najat M. |
author_facet |
Aburas,Najat M. Stevanovic,Nikola R. Milcic,Milos K. Lolic,Aleksandar D. Natic,Maja M. Tesic,Zivoslav Lj. Baosic,Rada M. |
author_role |
author |
author2 |
Stevanovic,Nikola R. Milcic,Milos K. Lolic,Aleksandar D. Natic,Maja M. Tesic,Zivoslav Lj. Baosic,Rada M. |
author2_role |
author author author author author author |
dc.contributor.author.fl_str_mv |
Aburas,Najat M. Stevanovic,Nikola R. Milcic,Milos K. Lolic,Aleksandar D. Natic,Maja M. Tesic,Zivoslav Lj. Baosic,Rada M. |
dc.subject.por.fl_str_mv |
antioxidant activity antioxidant mechanism Schiff base copper(II) complexes DFT |
topic |
antioxidant activity antioxidant mechanism Schiff base copper(II) complexes DFT |
description |
The influence of the structure on the antioxidant activity of a series of Schiff bases and their copper(II) complexes as well as possible mechanisms of antioxidant activity were investigated. Schiff bases are derived from the condensation of ethane-1,2-diamine or propane-1,2-diamine and pentane-2,4-dione and/or 1-phenylbutane-1,3-dione. The corresponding complexes were synthesized. The antioxidant activity in vitro, determined using reversed-phase thin layer chromatography assay (RP TLC) based on the reaction with 2,2'-diphenyl-1-picrylhydrazyl, was expressed as Trolox equivalent antioxidant capacity (TEAC). The influence of the structure was observed on the basis of interpretable and informative descriptors calculated by hybrid density functional theory (DFT) methods. Structural features responsible for the antioxidant activity of the investigated compounds were discussed. Copper(II) complexes showed a significantly higher antioxidant activity than their corresponding ligands. Calculated quantum-chemical descriptors gave an insight to the reaction mechanism of the scavenging/antioxidant activity of tetradentate Schiff bases and their copper(II) complexes and two different reaction mechanisms were proposed. |
publishDate |
2013 |
dc.date.none.fl_str_mv |
2013-08-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000800013 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000800013 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.5935/0103-5053.20130167 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.24 n.8 2013 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
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1750318175243730944 |