Fluorescence properties of a potential antitumoral benzothieno[3,2-b]pyrrole in solution and lipid membranes

Detalhes bibliográficos
Autor(a) principal: Castanheira, Elisabete M. S.
Data de Publicação: 2009
Outros Autores: Abreu, Ana S., Queiroz, Maria João R. P., Ferreira, Paula M. T., Coutinho, Paulo J. G., Nazareth, N., Nascimento, Maria São José
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: https://hdl.handle.net/1822/11762
Resumo: Fluorescence properties of the antitumoral methyl 3-(benzo[b]thien-2-yl)-benzothieno[3,2-b]pyrrole-2-carboxylate (BTP) were studied in solution and in lipid bilayers of dipalmitoyl phosphatidylcholine (DPPC), dioleoyl phosphatidylethanolamine (DOPE) and egg yolk phosphatidylcholine (Egg-PC). BTP presents good fluorescence quantum yields in all solvents studied (0.20 ≤ ΦF ≤ 0.32) and a bathochromic shift in polar solvents. The results indicate an ICT character of the excited state, with an estimated dipole moment of μe = 7.38 D. Fluorescence (steady-state) anisotropy measurements of BTP incorporated in lipid membranes of DPPC, DOPE and Egg-PC indicate that this compound is deeply located in the lipid bilayer, feeling the difference between the rigid gel phase and fluid phases. BTP inhibits the growth of three human tumour cell lines, MCF-7 (breast adenocarcinoma), SF-268 (glioma) and NCI-H460 (non-small cell lung cancer), being significantly more potent against the NCI-H460 tumour cells.
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spelling Fluorescence properties of a potential antitumoral benzothieno[3,2-b]pyrrole in solution and lipid membranesBenzothienopyrroleAntitumour propertiesFluorescenceLipid membranesScience & TechnologyFluorescence properties of the antitumoral methyl 3-(benzo[b]thien-2-yl)-benzothieno[3,2-b]pyrrole-2-carboxylate (BTP) were studied in solution and in lipid bilayers of dipalmitoyl phosphatidylcholine (DPPC), dioleoyl phosphatidylethanolamine (DOPE) and egg yolk phosphatidylcholine (Egg-PC). BTP presents good fluorescence quantum yields in all solvents studied (0.20 ≤ ΦF ≤ 0.32) and a bathochromic shift in polar solvents. The results indicate an ICT character of the excited state, with an estimated dipole moment of μe = 7.38 D. Fluorescence (steady-state) anisotropy measurements of BTP incorporated in lipid membranes of DPPC, DOPE and Egg-PC indicate that this compound is deeply located in the lipid bilayer, feeling the difference between the rigid gel phase and fluid phases. BTP inhibits the growth of three human tumour cell lines, MCF-7 (breast adenocarcinoma), SF-268 (glioma) and NCI-H460 (non-small cell lung cancer), being significantly more potent against the NCI-H460 tumour cells.Fundação para a Ciência e a Tecnologia (FCT) – projecto SeARCH (ref. REEQ/443/EEI/2005), bolsa SFRH/BPD/24548/2005, projecto PTDC/QUI/81238/2006European Communitarian Fund (FEDER)ElsevierUniversidade do MinhoCastanheira, Elisabete M. S.Abreu, Ana S.Queiroz, Maria João R. P.Ferreira, Paula M. T.Coutinho, Paulo J. G.Nazareth, N.Nascimento, Maria São José2009-082009-08-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/1822/11762eng"Journal of Photochemistry and Photobiology A. Chemistry" ISSN 1010-6030. 206:2-3 (Ago. 2009) 220-226.1010-603010.1016/j.jphotochem.2009.07.007www.sciencedirect.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:RCAAP2023-07-21T12:23:49ZPortal AgregadorONG
dc.title.none.fl_str_mv Fluorescence properties of a potential antitumoral benzothieno[3,2-b]pyrrole in solution and lipid membranes
title Fluorescence properties of a potential antitumoral benzothieno[3,2-b]pyrrole in solution and lipid membranes
spellingShingle Fluorescence properties of a potential antitumoral benzothieno[3,2-b]pyrrole in solution and lipid membranes
Castanheira, Elisabete M. S.
Benzothienopyrrole
Antitumour properties
Fluorescence
Lipid membranes
Science & Technology
title_short Fluorescence properties of a potential antitumoral benzothieno[3,2-b]pyrrole in solution and lipid membranes
title_full Fluorescence properties of a potential antitumoral benzothieno[3,2-b]pyrrole in solution and lipid membranes
title_fullStr Fluorescence properties of a potential antitumoral benzothieno[3,2-b]pyrrole in solution and lipid membranes
title_full_unstemmed Fluorescence properties of a potential antitumoral benzothieno[3,2-b]pyrrole in solution and lipid membranes
title_sort Fluorescence properties of a potential antitumoral benzothieno[3,2-b]pyrrole in solution and lipid membranes
author Castanheira, Elisabete M. S.
author_facet Castanheira, Elisabete M. S.
Abreu, Ana S.
Queiroz, Maria João R. P.
Ferreira, Paula M. T.
Coutinho, Paulo J. G.
Nazareth, N.
Nascimento, Maria São José
author_role author
author2 Abreu, Ana S.
Queiroz, Maria João R. P.
Ferreira, Paula M. T.
Coutinho, Paulo J. G.
Nazareth, N.
Nascimento, Maria São José
author2_role author
author
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.
Queiroz, Maria João R. P.
Ferreira, Paula M. T.
Coutinho, Paulo J. G.
Nazareth, N.
Nascimento, Maria São José
dc.subject.por.fl_str_mv Benzothienopyrrole
Antitumour properties
Fluorescence
Lipid membranes
Science & Technology
topic Benzothienopyrrole
Antitumour properties
Fluorescence
Lipid membranes
Science & Technology
description Fluorescence properties of the antitumoral methyl 3-(benzo[b]thien-2-yl)-benzothieno[3,2-b]pyrrole-2-carboxylate (BTP) were studied in solution and in lipid bilayers of dipalmitoyl phosphatidylcholine (DPPC), dioleoyl phosphatidylethanolamine (DOPE) and egg yolk phosphatidylcholine (Egg-PC). BTP presents good fluorescence quantum yields in all solvents studied (0.20 ≤ ΦF ≤ 0.32) and a bathochromic shift in polar solvents. The results indicate an ICT character of the excited state, with an estimated dipole moment of μe = 7.38 D. Fluorescence (steady-state) anisotropy measurements of BTP incorporated in lipid membranes of DPPC, DOPE and Egg-PC indicate that this compound is deeply located in the lipid bilayer, feeling the difference between the rigid gel phase and fluid phases. BTP inhibits the growth of three human tumour cell lines, MCF-7 (breast adenocarcinoma), SF-268 (glioma) and NCI-H460 (non-small cell lung cancer), being significantly more potent against the NCI-H460 tumour cells.
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 https://hdl.handle.net/1822/11762
url https://hdl.handle.net/1822/11762
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv "Journal of Photochemistry and Photobiology A. Chemistry" ISSN 1010-6030. 206:2-3 (Ago. 2009) 220-226.
1010-6030
10.1016/j.jphotochem.2009.07.007
www.sciencedirect.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 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
repository.mail.fl_str_mv
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