4-(4,5-Diphenyl-1H-imidazole-2-yl)-N,N-dimethylaniline-Cu(II) complex, a highly selective probe for glutathione sensing in water-acetonitrile mixtures

Detalhes bibliográficos
Autor(a) principal: Hazem, E. O.
Data de Publicação: 2018
Outros Autores: Sayed, S. E., Ferreira, R. C. M., Costa, Susana P. G., Raposo, M. Manuela M., Martínez-Máñez, R., Sancenón, F.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/57133
Resumo: The imidazole derivative 4-(4,5-diphenyl-1H-imidazol-2-yl)-N,N-dimethylaniline (probe 1) formed a highly coloured and non-emissive 1:1 stoichiometry complex with Cu(II) in water-acetonitrile 1:1 (v/v) solutions. Among all the amino acids (Lys, Val, Gln, Leu, His, Thr, Trp, Gly, Phe, Arg, Ile, Met, Ser, Ala, Pro, Tyr, Gly, Asn, Asp, Glu, Cys and Hcy) and tripeptides (GSH) tested, only GSH induced the bleaching of the 1·Cu(II) solution together with a marked emission enhancement at 411 nm (excitation at 320 nm). These chromo-fluorogenic changes were ascribed to a selective GSH-induced demetallation of the 1·Cu(II) complex that resulted in a recovery of the spectroscopic features of probe 1. In addition to the remarkable selectivity of 1·Cu(II) complex toward GSH a competitive limit of detection as low as 2 μM was determined using fluorescence measurements.
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spelling 4-(4,5-Diphenyl-1H-imidazole-2-yl)-N,N-dimethylaniline-Cu(II) complex, a highly selective probe for glutathione sensing in water-acetonitrile mixturesGlutathioneChromo-fluorogenic detectionCu(II) complexDisplacement assaysynthesisheterocyclesimidazoleoptical chemosensorfluoresecenceCiências Naturais::Ciências QuímicasScience & TechnologyThe imidazole derivative 4-(4,5-diphenyl-1H-imidazol-2-yl)-N,N-dimethylaniline (probe 1) formed a highly coloured and non-emissive 1:1 stoichiometry complex with Cu(II) in water-acetonitrile 1:1 (v/v) solutions. Among all the amino acids (Lys, Val, Gln, Leu, His, Thr, Trp, Gly, Phe, Arg, Ile, Met, Ser, Ala, Pro, Tyr, Gly, Asn, Asp, Glu, Cys and Hcy) and tripeptides (GSH) tested, only GSH induced the bleaching of the 1·Cu(II) solution together with a marked emission enhancement at 411 nm (excitation at 320 nm). These chromo-fluorogenic changes were ascribed to a selective GSH-induced demetallation of the 1·Cu(II) complex that resulted in a recovery of the spectroscopic features of probe 1. In addition to the remarkable selectivity of 1·Cu(II) complex toward GSH a competitive limit of detection as low as 2 μM was determined using fluorescence measurements.We thank the Spanish Government (MAT2015-64139-C4-1-R) and Generalitat Valenciana (PROMETEOII/2014/047). H. E. O. thanks Generalitat Valenciana for his Grisolia fellowship. Thanks are also due to Fundação para a Ciência e Tecnologia (Portugal) for financial support to the Portuguese NMR network (PTNMR, Bruker Avance III 400-Univ. Minho), FCT and FEDEReCOMPETEQREN-EU for financial support to the research centre CQUM (UID/QUI/0686/2016) and a doctoral grant to R.C.M. Ferreira (SFRH/BD/86408/2012). The NMR spectrometers are part of the National NMR Network (PTNMR) and are partially supported by Infrastructure Project No 022161 (co-financed by FEDER through COMPETE 2020, POCI and PORL and FCT through PIDDAC).info:eu-repo/semantics/publishedVersionElsevierUniversidade do MinhoHazem, E. O.Sayed, S. E.Ferreira, R. C. M.Costa, Susana P. G.Raposo, M. Manuela M.Martínez-Máñez, R.Sancenón, F.20182018-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfapplication/pdfhttp://hdl.handle.net/1822/57133engHazem, E. O.; Sayed, S. E.; Ferreira, R. C. M.; Costa, S. P. G.; Raposo, M. M. M., Martínez-Máñez, R.; Sancenón, F. 4-(4,5-Diphenyl-1H-imidazole-2-yl)-N,N-dimethylaniline-Cu(II) complex, a highly selective probe for glutathione sensing in water-acetonitrile mixtures. Dyes Pigments 2018, 159, 45-48.0143-720810.1016/j.dyepig.2018.05.069https://www.sciencedirect.com/science/article/pii/S0143720818309495info: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:RCAAP2023-07-21T12:47:44ZPortal AgregadorONG
dc.title.none.fl_str_mv 4-(4,5-Diphenyl-1H-imidazole-2-yl)-N,N-dimethylaniline-Cu(II) complex, a highly selective probe for glutathione sensing in water-acetonitrile mixtures
title 4-(4,5-Diphenyl-1H-imidazole-2-yl)-N,N-dimethylaniline-Cu(II) complex, a highly selective probe for glutathione sensing in water-acetonitrile mixtures
spellingShingle 4-(4,5-Diphenyl-1H-imidazole-2-yl)-N,N-dimethylaniline-Cu(II) complex, a highly selective probe for glutathione sensing in water-acetonitrile mixtures
Hazem, E. O.
Glutathione
Chromo-fluorogenic detection
Cu(II) complex
Displacement assay
synthesis
heterocycles
imidazole
optical chemosensor
fluoresecence
Ciências Naturais::Ciências Químicas
Science & Technology
title_short 4-(4,5-Diphenyl-1H-imidazole-2-yl)-N,N-dimethylaniline-Cu(II) complex, a highly selective probe for glutathione sensing in water-acetonitrile mixtures
title_full 4-(4,5-Diphenyl-1H-imidazole-2-yl)-N,N-dimethylaniline-Cu(II) complex, a highly selective probe for glutathione sensing in water-acetonitrile mixtures
title_fullStr 4-(4,5-Diphenyl-1H-imidazole-2-yl)-N,N-dimethylaniline-Cu(II) complex, a highly selective probe for glutathione sensing in water-acetonitrile mixtures
title_full_unstemmed 4-(4,5-Diphenyl-1H-imidazole-2-yl)-N,N-dimethylaniline-Cu(II) complex, a highly selective probe for glutathione sensing in water-acetonitrile mixtures
title_sort 4-(4,5-Diphenyl-1H-imidazole-2-yl)-N,N-dimethylaniline-Cu(II) complex, a highly selective probe for glutathione sensing in water-acetonitrile mixtures
author Hazem, E. O.
author_facet Hazem, E. O.
Sayed, S. E.
Ferreira, R. C. M.
Costa, Susana P. G.
Raposo, M. Manuela M.
Martínez-Máñez, R.
Sancenón, F.
author_role author
author2 Sayed, S. E.
Ferreira, R. C. M.
Costa, Susana P. G.
Raposo, M. Manuela M.
Martínez-Máñez, R.
Sancenón, F.
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Hazem, E. O.
Sayed, S. E.
Ferreira, R. C. M.
Costa, Susana P. G.
Raposo, M. Manuela M.
Martínez-Máñez, R.
Sancenón, F.
dc.subject.por.fl_str_mv Glutathione
Chromo-fluorogenic detection
Cu(II) complex
Displacement assay
synthesis
heterocycles
imidazole
optical chemosensor
fluoresecence
Ciências Naturais::Ciências Químicas
Science & Technology
topic Glutathione
Chromo-fluorogenic detection
Cu(II) complex
Displacement assay
synthesis
heterocycles
imidazole
optical chemosensor
fluoresecence
Ciências Naturais::Ciências Químicas
Science & Technology
description The imidazole derivative 4-(4,5-diphenyl-1H-imidazol-2-yl)-N,N-dimethylaniline (probe 1) formed a highly coloured and non-emissive 1:1 stoichiometry complex with Cu(II) in water-acetonitrile 1:1 (v/v) solutions. Among all the amino acids (Lys, Val, Gln, Leu, His, Thr, Trp, Gly, Phe, Arg, Ile, Met, Ser, Ala, Pro, Tyr, Gly, Asn, Asp, Glu, Cys and Hcy) and tripeptides (GSH) tested, only GSH induced the bleaching of the 1·Cu(II) solution together with a marked emission enhancement at 411 nm (excitation at 320 nm). These chromo-fluorogenic changes were ascribed to a selective GSH-induced demetallation of the 1·Cu(II) complex that resulted in a recovery of the spectroscopic features of probe 1. In addition to the remarkable selectivity of 1·Cu(II) complex toward GSH a competitive limit of detection as low as 2 μM was determined using fluorescence measurements.
publishDate 2018
dc.date.none.fl_str_mv 2018
2018-01-01T00:00:00Z
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/1822/57133
url http://hdl.handle.net/1822/57133
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Hazem, E. O.; Sayed, S. E.; Ferreira, R. C. M.; Costa, S. P. G.; Raposo, M. M. M., Martínez-Máñez, R.; Sancenón, F. 4-(4,5-Diphenyl-1H-imidazole-2-yl)-N,N-dimethylaniline-Cu(II) complex, a highly selective probe for glutathione sensing in water-acetonitrile mixtures. Dyes Pigments 2018, 159, 45-48.
0143-7208
10.1016/j.dyepig.2018.05.069
https://www.sciencedirect.com/science/article/pii/S0143720818309495
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
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repository.mail.fl_str_mv
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