Influence of the structure on the antioxidant activity of tetradentate schiff bases and their copper(II) complexes: possible mechanisms

Detalhes bibliográficos
Autor(a) principal: Aburas,Najat M.
Data de Publicação: 2013
Outros Autores: Stevanovic,Nikola R., Milcic,Milos K., Lolic,Aleksandar D., Natic,Maja M., Tesic,Zivoslav Lj., Baosic,Rada M.
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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spelling 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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