Fluorescence studies on potential antitumoral heteroaryl and heteroannulated indoles in solution and in lipid membranes

Detalhes bibliográficos
Autor(a) principal: Castanheira, Elisabete M. S.
Data de Publicação: 2009
Outros Autores: Abreu, Ana S., Carvalho, M. Solange D., Queiroz, Maria João R. P., Ferreira, Paula M. T.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/9916
Resumo: Fluorescence properties of three potential antitumoral compounds, a 3-(dibenzothien-4-yl)indole 1, a phenylbenzothienoindole 2 and a 3-(dibenzofur-4-yl)indole 3, were studied in solution and in lipid aggregates of dipalmitoyl phosphatidylcholine (DPPC), dioleoyl phosphatidylethanolamine (DOPE) and egg yolk phosphatidylcholine (Egg-PC). The 3-(dibenzofur-4-yl)indole 3 exhibits the higher fluorescence quantum yields in all solvents studied (0.32 ≤ ΦF ≤ 0.51). All the compounds present a solvent sensitive emission, with significant red shifts in alcohols. The results point to an ICT character of the excited state, more pronounced for compound 1. Fluorescence (steady-state) anisotropy measurements of the compounds incorporated in lipid aggregates of DPPC, DOPE and Egg-PC indicate that the three compounds are deeply located in the lipid bilayer, feeling the difference between the rigid gel phase and fluid phases.
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spelling Fluorescence studies on potential antitumoral heteroaryl and heteroannulated indoles in solution and in lipid membranesHeteroaryl and heteroannulated indolesLipid membranesFluorescence anisotropyScience & TechnologyFluorescence properties of three potential antitumoral compounds, a 3-(dibenzothien-4-yl)indole 1, a phenylbenzothienoindole 2 and a 3-(dibenzofur-4-yl)indole 3, were studied in solution and in lipid aggregates of dipalmitoyl phosphatidylcholine (DPPC), dioleoyl phosphatidylethanolamine (DOPE) and egg yolk phosphatidylcholine (Egg-PC). The 3-(dibenzofur-4-yl)indole 3 exhibits the higher fluorescence quantum yields in all solvents studied (0.32 ≤ ΦF ≤ 0.51). All the compounds present a solvent sensitive emission, with significant red shifts in alcohols. The results point to an ICT character of the excited state, more pronounced for compound 1. Fluorescence (steady-state) anisotropy measurements of the compounds incorporated in lipid aggregates of DPPC, DOPE and Egg-PC indicate that the three compounds are deeply located in the lipid bilayer, feeling the difference between the rigid gel phase and fluid phases.Fundação para a Ciência e a Tecnologia (FCT) - Projecto POCI/QUI/59407/2004, bolsa doutoramento SFRH/BPD/24548/2005Fundo Europeu de Desenvolvimento Regional (FEDER)SpringerUniversidade do MinhoCastanheira, Elisabete M. S.Abreu, Ana S.Carvalho, M. Solange D.Queiroz, Maria João R. P.Ferreira, Paula M. T.2009-052009-05-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/9916eng"Journal of Fluorescence." ISSN 1053-0509. 19:3 (Maio 2009) 501-509.1053-050910.1007/s10895-008-0439-619043780www.springerlink.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:RCAAP2023-07-21T11:57:07ZPortal AgregadorONG
dc.title.none.fl_str_mv Fluorescence studies on potential antitumoral heteroaryl and heteroannulated indoles in solution and in lipid membranes
title Fluorescence studies on potential antitumoral heteroaryl and heteroannulated indoles in solution and in lipid membranes
spellingShingle Fluorescence studies on potential antitumoral heteroaryl and heteroannulated indoles in solution and in lipid membranes
Castanheira, Elisabete M. S.
Heteroaryl and heteroannulated indoles
Lipid membranes
Fluorescence anisotropy
Science & Technology
title_short Fluorescence studies on potential antitumoral heteroaryl and heteroannulated indoles in solution and in lipid membranes
title_full Fluorescence studies on potential antitumoral heteroaryl and heteroannulated indoles in solution and in lipid membranes
title_fullStr Fluorescence studies on potential antitumoral heteroaryl and heteroannulated indoles in solution and in lipid membranes
title_full_unstemmed Fluorescence studies on potential antitumoral heteroaryl and heteroannulated indoles in solution and in lipid membranes
title_sort Fluorescence studies on potential antitumoral heteroaryl and heteroannulated indoles in solution and in lipid membranes
author Castanheira, Elisabete M. S.
author_facet Castanheira, Elisabete M. S.
Abreu, Ana S.
Carvalho, M. Solange D.
Queiroz, Maria João R. P.
Ferreira, Paula M. T.
author_role author
author2 Abreu, Ana S.
Carvalho, M. Solange D.
Queiroz, Maria João R. P.
Ferreira, Paula M. T.
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Castanheira, Elisabete M. S.
Abreu, Ana S.
Carvalho, M. Solange D.
Queiroz, Maria João R. P.
Ferreira, Paula M. T.
dc.subject.por.fl_str_mv Heteroaryl and heteroannulated indoles
Lipid membranes
Fluorescence anisotropy
Science & Technology
topic Heteroaryl and heteroannulated indoles
Lipid membranes
Fluorescence anisotropy
Science & Technology
description Fluorescence properties of three potential antitumoral compounds, a 3-(dibenzothien-4-yl)indole 1, a phenylbenzothienoindole 2 and a 3-(dibenzofur-4-yl)indole 3, were studied in solution and in lipid aggregates of dipalmitoyl phosphatidylcholine (DPPC), dioleoyl phosphatidylethanolamine (DOPE) and egg yolk phosphatidylcholine (Egg-PC). The 3-(dibenzofur-4-yl)indole 3 exhibits the higher fluorescence quantum yields in all solvents studied (0.32 ≤ ΦF ≤ 0.51). All the compounds present a solvent sensitive emission, with significant red shifts in alcohols. The results point to an ICT character of the excited state, more pronounced for compound 1. Fluorescence (steady-state) anisotropy measurements of the compounds incorporated in lipid aggregates of DPPC, DOPE and Egg-PC indicate that the three compounds are deeply located in the lipid bilayer, feeling the difference between the rigid gel phase and fluid phases.
publishDate 2009
dc.date.none.fl_str_mv 2009-05
2009-05-01T00:00:00Z
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/1822/9916
url http://hdl.handle.net/1822/9916
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv "Journal of Fluorescence." ISSN 1053-0509. 19:3 (Maio 2009) 501-509.
1053-0509
10.1007/s10895-008-0439-6
19043780
www.springerlink.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 Springer
publisher.none.fl_str_mv Springer
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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