Synthesis and photophysical studies of a pyrenylindole and a phenalenoindole obtained from dehydroamino acid derivatives : application as fluorescent probes for biological systems

Detalhes bibliográficos
Autor(a) principal: Pereira, Goreti
Data de Publicação: 2009
Outros Autores: Abreu, Ana S., Castanheira, Elisabete M. S., Coutinho, Paulo J. G., Ferreira, Paula M. T., Queiroz, Maria João R. P.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/9917
Resumo: Two pyrenyl-dehydroamino acid derivatives were cyclized by a metal-assisted C–N intramolecular cyclization developed in our research group, to give a pyrenylindole and a phenalenoindole. The pyrenylindole was inserted into a peptide by solid-phase coupling, with use of a 2-chlorotrityl chloride resin and a Fmoc strategy. The photophysical properties of the pyrenylindole and phenalenoindole in several solvents were studied and showed that these compounds can be used as fluorescence probes. The results obtained with the peptide labelled with the pyrenylindole moiety show potential for use of this compound as a fluorescence label avoiding the aggregation propensity of pyrene compounds. Photophysical studies of the pyrenylindole and of the phenalenoindole in lipid membranes were also carried out. Steady-state fluorescence anisotropy measurements revealed that both compounds adopt locations inside the lipid bilayers and are able to report the transition between the gel and liquid-crystalline phases. The results point to potential use of these compounds as fluorescent probes for biological systems.
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spelling Synthesis and photophysical studies of a pyrenylindole and a phenalenoindole obtained from dehydroamino acid derivatives : application as fluorescent probes for biological systemsCyclizationPalladiumPeptidesFluorescent probesNitrogen heterocyclesMembranesScience & TechnologyTwo pyrenyl-dehydroamino acid derivatives were cyclized by a metal-assisted C–N intramolecular cyclization developed in our research group, to give a pyrenylindole and a phenalenoindole. The pyrenylindole was inserted into a peptide by solid-phase coupling, with use of a 2-chlorotrityl chloride resin and a Fmoc strategy. The photophysical properties of the pyrenylindole and phenalenoindole in several solvents were studied and showed that these compounds can be used as fluorescence probes. The results obtained with the peptide labelled with the pyrenylindole moiety show potential for use of this compound as a fluorescence label avoiding the aggregation propensity of pyrene compounds. Photophysical studies of the pyrenylindole and of the phenalenoindole in lipid membranes were also carried out. Steady-state fluorescence anisotropy measurements revealed that both compounds adopt locations inside the lipid bilayers and are able to report the transition between the gel and liquid-crystalline phases. The results point to potential use of these compounds as fluorescent probes for biological systems.Fundação para a Ciência e a Tecnologia (FCT) - (SFRH/BPD/24548/2005), (SFRH/BD/38766/2007)Fundo Europeu de Desenvolvimento Regional (FEDER) - Project PTDC/QUI/81238/2006WileyUniversidade do MinhoPereira, GoretiAbreu, Ana S.Castanheira, Elisabete M. S.Coutinho, Paulo J. G.Ferreira, Paula M. T.Queiroz, Maria João R. P.2009-082009-08-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/9917eng"European Journal of Organic Chemistry." ISSN 1434-193X. 2009:23 (Ago. 2009) 3906–3916.1434-193X10.1002/ejoc.200900351www3.interscience.wiley.cominfo: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:RCAAP2023-07-21T12:33:39ZPortal AgregadorONG
dc.title.none.fl_str_mv Synthesis and photophysical studies of a pyrenylindole and a phenalenoindole obtained from dehydroamino acid derivatives : application as fluorescent probes for biological systems
title Synthesis and photophysical studies of a pyrenylindole and a phenalenoindole obtained from dehydroamino acid derivatives : application as fluorescent probes for biological systems
spellingShingle Synthesis and photophysical studies of a pyrenylindole and a phenalenoindole obtained from dehydroamino acid derivatives : application as fluorescent probes for biological systems
Pereira, Goreti
Cyclization
Palladium
Peptides
Fluorescent probes
Nitrogen heterocycles
Membranes
Science & Technology
title_short Synthesis and photophysical studies of a pyrenylindole and a phenalenoindole obtained from dehydroamino acid derivatives : application as fluorescent probes for biological systems
title_full Synthesis and photophysical studies of a pyrenylindole and a phenalenoindole obtained from dehydroamino acid derivatives : application as fluorescent probes for biological systems
title_fullStr Synthesis and photophysical studies of a pyrenylindole and a phenalenoindole obtained from dehydroamino acid derivatives : application as fluorescent probes for biological systems
title_full_unstemmed Synthesis and photophysical studies of a pyrenylindole and a phenalenoindole obtained from dehydroamino acid derivatives : application as fluorescent probes for biological systems
title_sort Synthesis and photophysical studies of a pyrenylindole and a phenalenoindole obtained from dehydroamino acid derivatives : application as fluorescent probes for biological systems
author Pereira, Goreti
author_facet Pereira, Goreti
Abreu, Ana S.
Castanheira, Elisabete M. S.
Coutinho, Paulo J. G.
Ferreira, Paula M. T.
Queiroz, Maria João R. P.
author_role author
author2 Abreu, Ana S.
Castanheira, Elisabete M. S.
Coutinho, Paulo J. G.
Ferreira, Paula M. T.
Queiroz, Maria João R. P.
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Pereira, Goreti
Abreu, Ana S.
Castanheira, Elisabete M. S.
Coutinho, Paulo J. G.
Ferreira, Paula M. T.
Queiroz, Maria João R. P.
dc.subject.por.fl_str_mv Cyclization
Palladium
Peptides
Fluorescent probes
Nitrogen heterocycles
Membranes
Science & Technology
topic Cyclization
Palladium
Peptides
Fluorescent probes
Nitrogen heterocycles
Membranes
Science & Technology
description Two pyrenyl-dehydroamino acid derivatives were cyclized by a metal-assisted C–N intramolecular cyclization developed in our research group, to give a pyrenylindole and a phenalenoindole. The pyrenylindole was inserted into a peptide by solid-phase coupling, with use of a 2-chlorotrityl chloride resin and a Fmoc strategy. The photophysical properties of the pyrenylindole and phenalenoindole in several solvents were studied and showed that these compounds can be used as fluorescence probes. The results obtained with the peptide labelled with the pyrenylindole moiety show potential for use of this compound as a fluorescence label avoiding the aggregation propensity of pyrene compounds. Photophysical studies of the pyrenylindole and of the phenalenoindole in lipid membranes were also carried out. Steady-state fluorescence anisotropy measurements revealed that both compounds adopt locations inside the lipid bilayers and are able to report the transition between the gel and liquid-crystalline phases. The results point to potential use of these compounds as fluorescent probes for biological systems.
publishDate 2009
dc.date.none.fl_str_mv 2009-08
2009-08-01T00:00:00Z
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/1822/9917
url http://hdl.handle.net/1822/9917
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv "European Journal of Organic Chemistry." ISSN 1434-193X. 2009:23 (Ago. 2009) 3906–3916.
1434-193X
10.1002/ejoc.200900351
www3.interscience.wiley.com
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 Wiley
publisher.none.fl_str_mv Wiley
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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