Phenanthrenyl-indole as a fluorescent probe for peptides and lipid membranes

Detalhes bibliográficos
Autor(a) principal: Hermenegildo, Bruno F.
Data de Publicação: 2011
Outros Autores: Pereira, Goreti, Abreu, Ana S., Castanheira, Elisabete M. S., 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: https://hdl.handle.net/1822/12478
Resumo: Prova tipográfica
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spelling Phenanthrenyl-indole as a fluorescent probe for peptides and lipid membranesPhenanthrenyl-indoleRGD peptideFluorescenceLipid membraresLipid membranesScience & TechnologyProva tipográficaA 3-(phenanthren-9-yl)-1H-indole-2-carboxylic acid (2) obtained from the cleavage of the methyl ester of the methyl 3-(phenanthren-9-yl)-1H-indole-2-carboxylate (1) was inserted into a peptide containing the RGD sequence. The GGRGDG peptide sequence was prepared by solid phase synthesis and coupled to compound (2), using diisopropylcarbodiimide (DIC) and 1-hydroxybenzotriazole (HOBt) in DMF. The peptide (3) labelled with the phenanthrenylindole moiety was obtained in 31% yield. The photophysical properties of the phenanthrenyl-indole derivatives were studied in several solvents of different polarity. Compounds 1 and 2 have reasonably high fluorescence quantum yields (between 27% and 85%) in non-protic solvents, the methyl phenanthrenyl-indole-2-carboxylate 1 being the more fluorescent compound. The fluorescence emission of both compounds is sensitive to solvent, indicating that they are good candidates for fluorescent probes. Fluorescence emission measurements of the labelled peptide in solution showed a strong decrease of fluorescence quantum yield value caused by the attachment of the Gly-Gly-Arg-Gly-Asp-Gly chain. The phenanthrenyl-indoles 1 and 2 and the labelled peptide 3 were incorporated in liposomes of dipalmitoyl phosphatidylcholine (DPPC) and dipalmitoyl phosphatidylglycerol (DPPG) and mixtures of both lipids. Steady-state anisotropy measurements showed that compounds 1 and 2 are located inside the lipid bilayers and are able to report the transition between the gel and liquid-crystalline phases. The RGD labelled peptide locates mainly in the outer part of the vesicle interface. These results indicate that the phenanthrenyl-indole moiety may be used as a fluorescent probe for peptides and lipid membranes.Fundação para a Ciência e a Tecnologia (FCT) - projeto de investigação PTDC/QUI/81238/2006, Bolsa de doutoramento SFRH/BD/38766/2007, pós-doutoramento SFRH/BPD/24548/2005, "spectrometer Bruker Avance III 400" Portuguese NMR Network (Rede/1517/RMN/2005)Programa FEDER/COMPETE - FCOMP-01-0124-FEDER-007467Universidade do Minho. Centro de Física (CFUM)Universidade do Minho. Centro de Química (CQ-UM)ElsevierUniversidade do MinhoHermenegildo, Bruno F.Pereira, GoretiAbreu, Ana S.Castanheira, Elisabete M. S.Ferreira, Paula M. T.Queiroz, Maria João R. P.2011-04-292011-04-29T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/1822/12478engHermenegildo, B. F., Pereira, G., Abreu, A. S., Castanheira, E. M. S., Ferreira, P. M. T., & Queiroz, M.-J. R. P. (2011, June). Phenanthrenyl-indole as a fluorescent probe for peptides and lipid membranes. Journal of Photochemistry and Photobiology A: Chemistry. Elsevier BV. http://doi.org/10.1016/j.jphotochem.2011.04.0221010-603010.1016/j.jphotochem.2011.04.022https://www.sciencedirect.com/science/article/pii/S101060301100178Xinfo: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:RCAAP2023-07-21T11:58:58Zoai:repositorium.sdum.uminho.pt:1822/12478Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T18:48:44.331163Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Phenanthrenyl-indole as a fluorescent probe for peptides and lipid membranes
title Phenanthrenyl-indole as a fluorescent probe for peptides and lipid membranes
spellingShingle Phenanthrenyl-indole as a fluorescent probe for peptides and lipid membranes
Hermenegildo, Bruno F.
Phenanthrenyl-indole
RGD peptide
Fluorescence
Lipid membrares
Lipid membranes
Science & Technology
title_short Phenanthrenyl-indole as a fluorescent probe for peptides and lipid membranes
title_full Phenanthrenyl-indole as a fluorescent probe for peptides and lipid membranes
title_fullStr Phenanthrenyl-indole as a fluorescent probe for peptides and lipid membranes
title_full_unstemmed Phenanthrenyl-indole as a fluorescent probe for peptides and lipid membranes
title_sort Phenanthrenyl-indole as a fluorescent probe for peptides and lipid membranes
author Hermenegildo, Bruno F.
author_facet Hermenegildo, Bruno F.
Pereira, Goreti
Abreu, Ana S.
Castanheira, Elisabete M. S.
Ferreira, Paula M. T.
Queiroz, Maria João R. P.
author_role author
author2 Pereira, Goreti
Abreu, Ana S.
Castanheira, Elisabete M. S.
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 Hermenegildo, Bruno F.
Pereira, Goreti
Abreu, Ana S.
Castanheira, Elisabete M. S.
Ferreira, Paula M. T.
Queiroz, Maria João R. P.
dc.subject.por.fl_str_mv Phenanthrenyl-indole
RGD peptide
Fluorescence
Lipid membrares
Lipid membranes
Science & Technology
topic Phenanthrenyl-indole
RGD peptide
Fluorescence
Lipid membrares
Lipid membranes
Science & Technology
description Prova tipográfica
publishDate 2011
dc.date.none.fl_str_mv 2011-04-29
2011-04-29T00:00:00Z
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 https://hdl.handle.net/1822/12478
url https://hdl.handle.net/1822/12478
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Hermenegildo, B. F., Pereira, G., Abreu, A. S., Castanheira, E. M. S., Ferreira, P. M. T., & Queiroz, M.-J. R. P. (2011, June). Phenanthrenyl-indole as a fluorescent probe for peptides and lipid membranes. Journal of Photochemistry and Photobiology A: Chemistry. Elsevier BV. http://doi.org/10.1016/j.jphotochem.2011.04.022
1010-6030
10.1016/j.jphotochem.2011.04.022
https://www.sciencedirect.com/science/article/pii/S101060301100178X
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 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)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv
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