Synthesis of the first thieno-δ-carboline. Fluorescence studies in solution and in lipid vesicles
Autor(a) principal: | |
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Data de Publicação: | 2006 |
Outros Autores: | , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10198/828 |
Resumo: | The first thieno-δ-carboline (6,8,9-trimethyl-5H-pyrido[3,2-b]thieno[3,2-f]indole) was prepared in good yield (70%) by intramolecular palladium-assisted cyclization of an ortho-chlorodiarylamine. The latter was in turn selectively synthesized in high yield (90%) by C–N palladiumcatalyzed cross-coupling of 3-bromo-2-chloropyridine with, the also prepared, 6-amino-2,3,7-trimethylbenzo[b]thiophene. Fluorescence studies in solution show that thieno-δ-carboline has a solvatochromic behaviour. Despite the low fluorescence quantum yields in solution, studies of its incorporation in lipid vesicles of DPPC, DOPE and DODAB indicate that thienocarboline is located mainly inside the lipid bilayer, exhibiting different behaviours in gel or liquid-crystalline phases. Our studies are useful for the incorporation of thienocarboline in liposomes and for controlled drug release assays, due to its biological activity. |
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Synthesis of the first thieno-δ-carboline. Fluorescence studies in solution and in lipid vesiclesPalladium-assisted reactionsThieno-δ-carbolineFluorescenceSolvatochromic probesLipid vesiclesThe first thieno-δ-carboline (6,8,9-trimethyl-5H-pyrido[3,2-b]thieno[3,2-f]indole) was prepared in good yield (70%) by intramolecular palladium-assisted cyclization of an ortho-chlorodiarylamine. The latter was in turn selectively synthesized in high yield (90%) by C–N palladiumcatalyzed cross-coupling of 3-bromo-2-chloropyridine with, the also prepared, 6-amino-2,3,7-trimethylbenzo[b]thiophene. Fluorescence studies in solution show that thieno-δ-carboline has a solvatochromic behaviour. Despite the low fluorescence quantum yields in solution, studies of its incorporation in lipid vesicles of DPPC, DOPE and DODAB indicate that thienocarboline is located mainly inside the lipid bilayer, exhibiting different behaviours in gel or liquid-crystalline phases. Our studies are useful for the incorporation of thienocarboline in liposomes and for controlled drug release assays, due to its biological activity.ElsevierBiblioteca Digital do IPBQueiroz, Maria João R.P.Castanheira, Elisabete M.S.Pinto, Ana M.R.Ferreira, Isabel C.F.R.Begouin, AgatheKirsch, Gilbert2008-09-12T15:20:38Z20062006-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10198/828engQueiroz, Maria João R.P.; Castanheira, Elisabete M.S.; Pinto, Ana M.R.; Ferreira, Isabel C.F.R.; Begouin, Agathe; Kirsch, Gilbert (2006). Synthesis of the first thieno-δ-carboline. Fluorescence studies in solution and in lipid vesicles. Journal of Photochemistry and Photobiology A: Chemistry. ISSN 1010-6030. 181:2-3, p. 290-2961010-603010.1016/j.jphotochem.2005.12.010info: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:RCAAP2023-11-21T10:03:56Zoai:bibliotecadigital.ipb.pt:10198/828Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T22:54:28.061991Repositório 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 |
Synthesis of the first thieno-δ-carboline. Fluorescence studies in solution and in lipid vesicles |
title |
Synthesis of the first thieno-δ-carboline. Fluorescence studies in solution and in lipid vesicles |
spellingShingle |
Synthesis of the first thieno-δ-carboline. Fluorescence studies in solution and in lipid vesicles Queiroz, Maria João R.P. Palladium-assisted reactions Thieno-δ-carboline Fluorescence Solvatochromic probes Lipid vesicles |
title_short |
Synthesis of the first thieno-δ-carboline. Fluorescence studies in solution and in lipid vesicles |
title_full |
Synthesis of the first thieno-δ-carboline. Fluorescence studies in solution and in lipid vesicles |
title_fullStr |
Synthesis of the first thieno-δ-carboline. Fluorescence studies in solution and in lipid vesicles |
title_full_unstemmed |
Synthesis of the first thieno-δ-carboline. Fluorescence studies in solution and in lipid vesicles |
title_sort |
Synthesis of the first thieno-δ-carboline. Fluorescence studies in solution and in lipid vesicles |
author |
Queiroz, Maria João R.P. |
author_facet |
Queiroz, Maria João R.P. Castanheira, Elisabete M.S. Pinto, Ana M.R. Ferreira, Isabel C.F.R. Begouin, Agathe Kirsch, Gilbert |
author_role |
author |
author2 |
Castanheira, Elisabete M.S. Pinto, Ana M.R. Ferreira, Isabel C.F.R. Begouin, Agathe Kirsch, Gilbert |
author2_role |
author author author author author |
dc.contributor.none.fl_str_mv |
Biblioteca Digital do IPB |
dc.contributor.author.fl_str_mv |
Queiroz, Maria João R.P. Castanheira, Elisabete M.S. Pinto, Ana M.R. Ferreira, Isabel C.F.R. Begouin, Agathe Kirsch, Gilbert |
dc.subject.por.fl_str_mv |
Palladium-assisted reactions Thieno-δ-carboline Fluorescence Solvatochromic probes Lipid vesicles |
topic |
Palladium-assisted reactions Thieno-δ-carboline Fluorescence Solvatochromic probes Lipid vesicles |
description |
The first thieno-δ-carboline (6,8,9-trimethyl-5H-pyrido[3,2-b]thieno[3,2-f]indole) was prepared in good yield (70%) by intramolecular palladium-assisted cyclization of an ortho-chlorodiarylamine. The latter was in turn selectively synthesized in high yield (90%) by C–N palladiumcatalyzed cross-coupling of 3-bromo-2-chloropyridine with, the also prepared, 6-amino-2,3,7-trimethylbenzo[b]thiophene. Fluorescence studies in solution show that thieno-δ-carboline has a solvatochromic behaviour. Despite the low fluorescence quantum yields in solution, studies of its incorporation in lipid vesicles of DPPC, DOPE and DODAB indicate that thienocarboline is located mainly inside the lipid bilayer, exhibiting different behaviours in gel or liquid-crystalline phases. Our studies are useful for the incorporation of thienocarboline in liposomes and for controlled drug release assays, due to its biological activity. |
publishDate |
2006 |
dc.date.none.fl_str_mv |
2006 2006-01-01T00:00:00Z 2008-09-12T15:20:38Z |
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/10198/828 |
url |
http://hdl.handle.net/10198/828 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Queiroz, Maria João R.P.; Castanheira, Elisabete M.S.; Pinto, Ana M.R.; Ferreira, Isabel C.F.R.; Begouin, Agathe; Kirsch, Gilbert (2006). Synthesis of the first thieno-δ-carboline. Fluorescence studies in solution and in lipid vesicles. Journal of Photochemistry and Photobiology A: Chemistry. ISSN 1010-6030. 181:2-3, p. 290-296 1010-6030 10.1016/j.jphotochem.2005.12.010 |
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 |
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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 |
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1799135143550517248 |