Synthesis of the first thieno-delta-carboline: fluorescence studies in solution and in lipid vesicles

Detalhes bibliográficos
Autor(a) principal: Queiroz, Maria João R. P.
Data de Publicação: 2006
Outros Autores: Castanheira, Elisabete M. S., Pinto, Ana M. R., Ferreira, Isabel C. F. R., Begouin, Agathe, Kirsch, G.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: https://hdl.handle.net/1822/5586
Resumo: The first thieno-delta-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 palladium catalyzed 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-delta-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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spelling Synthesis of the first thieno-delta-carboline: fluorescence studies in solution and in lipid vesiclesPalladium-assisted reactionsThieno-delta-carbolineFluorescenceSolvatochromic probesLipid vesiclesThieno-d-carbolineThieno-δ-carbolineScience & TechnologyThe first thieno-delta-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 palladium catalyzed 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-delta-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.Fundação para a Ciência e a Tecnologia (FCT)ElsevierUniversidade do MinhoQueiroz, Maria João R. P.Castanheira, Elisabete M. S.Pinto, Ana M. R.Ferreira, Isabel C. F. R.Begouin, AgatheKirsch, G.2006-072006-07-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/1822/5586eng"Journal of photochemistry and photobiology A : chemistry". ISSN 1010-6030. 181:2-3 (July 2006) 290-296.1010-603010.1016/j.jphotochem.2005.12.010The original publication is available at www.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:RCAAP2023-07-21T12:27:46Zoai:repositorium.sdum.uminho.pt:1822/5586Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:22:29.810005Repositório 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-delta-carboline: fluorescence studies in solution and in lipid vesicles
title Synthesis of the first thieno-delta-carboline: fluorescence studies in solution and in lipid vesicles
spellingShingle Synthesis of the first thieno-delta-carboline: fluorescence studies in solution and in lipid vesicles
Queiroz, Maria João R. P.
Palladium-assisted reactions
Thieno-delta-carboline
Fluorescence
Solvatochromic probes
Lipid vesicles
Thieno-d-carboline
Thieno-δ-carboline
Science & Technology
title_short Synthesis of the first thieno-delta-carboline: fluorescence studies in solution and in lipid vesicles
title_full Synthesis of the first thieno-delta-carboline: fluorescence studies in solution and in lipid vesicles
title_fullStr Synthesis of the first thieno-delta-carboline: fluorescence studies in solution and in lipid vesicles
title_full_unstemmed Synthesis of the first thieno-delta-carboline: fluorescence studies in solution and in lipid vesicles
title_sort Synthesis of the first thieno-delta-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, G.
author_role author
author2 Castanheira, Elisabete M. S.
Pinto, Ana M. R.
Ferreira, Isabel C. F. R.
Begouin, Agathe
Kirsch, G.
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
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, G.
dc.subject.por.fl_str_mv Palladium-assisted reactions
Thieno-delta-carboline
Fluorescence
Solvatochromic probes
Lipid vesicles
Thieno-d-carboline
Thieno-δ-carboline
Science & Technology
topic Palladium-assisted reactions
Thieno-delta-carboline
Fluorescence
Solvatochromic probes
Lipid vesicles
Thieno-d-carboline
Thieno-δ-carboline
Science & Technology
description The first thieno-delta-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 palladium catalyzed 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-delta-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 2006-07
2006-07-01T00:00:00Z
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/1822/5586
url https://hdl.handle.net/1822/5586
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. 181:2-3 (July 2006) 290-296.
1010-6030
10.1016/j.jphotochem.2005.12.010
The original publication is available at 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 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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