Acridinyl methyl esters as photoactive precursors in the release of neurotransmitter amino acids
Autor(a) principal: | |
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Data de Publicação: | 2013 |
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/1822/21961 |
Resumo: | An investigation of the use of an azaheterocycle, acridine, as an alternative photochemically removable protecting group for the carboxylic function of neurotransmitter amino acids was carried out. 9-Bromomethylacridine was used in the reaction with glycine, alanine, glutamic acid, β-alanine and γ-aminobutyric acid, to obtain model ester derivatives, which were irradiated at different wavelengths in a photochemical reactor. The process was followed by HPLC/UV, resulting in the release of the active molecule in short irradiation times. The results obtained using 419 nm irradiation show promise (35-98 min) for practical purposes. The compounds were further characterised via time-resolved fluorescence to elucidate their photophysical properties and determine the decay kinetics. |
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Acridinyl methyl esters as photoactive precursors in the release of neurotransmitter amino acidsAcridinyl methyl estersPhotocleavable protecting groupsNeurotransmittersAmino acidsCaged compoundsScience & TechnologyAn investigation of the use of an azaheterocycle, acridine, as an alternative photochemically removable protecting group for the carboxylic function of neurotransmitter amino acids was carried out. 9-Bromomethylacridine was used in the reaction with glycine, alanine, glutamic acid, β-alanine and γ-aminobutyric acid, to obtain model ester derivatives, which were irradiated at different wavelengths in a photochemical reactor. The process was followed by HPLC/UV, resulting in the release of the active molecule in short irradiation times. The results obtained using 419 nm irradiation show promise (35-98 min) for practical purposes. The compounds were further characterised via time-resolved fluorescence to elucidate their photophysical properties and determine the decay kinetics.Fundação para a Ciência e Tecnologia (FCT, Portugal) for financial support to the NMR portuguese network (PTNMR, Bruker Avance III 400-Univ. Minho), FCT and FEDER (European Fund for Regional Development)-COMPETE-QREN-EU for financial support to the research centre CQ/UM [PEst-C/QUI/UI0686/2011 (FCOMP-01-0124-FEDER-022716)] and project PTDC/QUI/69607/2006 (FCOMP-01-0124-FEDER-007449). FCT - a PhD grant to A.M.P. (SFRH/BD/61459/2009).Royal Society of ChemistryUniversidade do MinhoPiloto, Ana M.Hungerford, GrahamCosta, Susana P. G.Gonçalves, M. Sameiro T.20132013-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/21961engPiloto AM, Hungerford G, Costa SP, Gonçalves MS. Acridinyl methyl esters as photoactive precursors in the release of neurotransmitter amino acids. Photochem Photobiol Sci. 2013 Feb;12(2):339-47. doi: 10.1039/c2pp25261a.1474-905X10.1039/c2pp25261a23064410info: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:RCAAP2023-07-21T11:56:28Zoai:repositorium.sdum.uminho.pt:1822/21961Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T18:46:04.354574Repositório 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 |
Acridinyl methyl esters as photoactive precursors in the release of neurotransmitter amino acids |
title |
Acridinyl methyl esters as photoactive precursors in the release of neurotransmitter amino acids |
spellingShingle |
Acridinyl methyl esters as photoactive precursors in the release of neurotransmitter amino acids Piloto, Ana M. Acridinyl methyl esters Photocleavable protecting groups Neurotransmitters Amino acids Caged compounds Science & Technology |
title_short |
Acridinyl methyl esters as photoactive precursors in the release of neurotransmitter amino acids |
title_full |
Acridinyl methyl esters as photoactive precursors in the release of neurotransmitter amino acids |
title_fullStr |
Acridinyl methyl esters as photoactive precursors in the release of neurotransmitter amino acids |
title_full_unstemmed |
Acridinyl methyl esters as photoactive precursors in the release of neurotransmitter amino acids |
title_sort |
Acridinyl methyl esters as photoactive precursors in the release of neurotransmitter amino acids |
author |
Piloto, Ana M. |
author_facet |
Piloto, Ana M. Hungerford, Graham Costa, Susana P. G. Gonçalves, M. Sameiro T. |
author_role |
author |
author2 |
Hungerford, Graham Costa, Susana P. G. Gonçalves, M. Sameiro T. |
author2_role |
author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Piloto, Ana M. Hungerford, Graham Costa, Susana P. G. Gonçalves, M. Sameiro T. |
dc.subject.por.fl_str_mv |
Acridinyl methyl esters Photocleavable protecting groups Neurotransmitters Amino acids Caged compounds Science & Technology |
topic |
Acridinyl methyl esters Photocleavable protecting groups Neurotransmitters Amino acids Caged compounds Science & Technology |
description |
An investigation of the use of an azaheterocycle, acridine, as an alternative photochemically removable protecting group for the carboxylic function of neurotransmitter amino acids was carried out. 9-Bromomethylacridine was used in the reaction with glycine, alanine, glutamic acid, β-alanine and γ-aminobutyric acid, to obtain model ester derivatives, which were irradiated at different wavelengths in a photochemical reactor. The process was followed by HPLC/UV, resulting in the release of the active molecule in short irradiation times. The results obtained using 419 nm irradiation show promise (35-98 min) for practical purposes. The compounds were further characterised via time-resolved fluorescence to elucidate their photophysical properties and determine the decay kinetics. |
publishDate |
2013 |
dc.date.none.fl_str_mv |
2013 2013-01-01T00:00:00Z |
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/1822/21961 |
url |
http://hdl.handle.net/1822/21961 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Piloto AM, Hungerford G, Costa SP, Gonçalves MS. Acridinyl methyl esters as photoactive precursors in the release of neurotransmitter amino acids. Photochem Photobiol Sci. 2013 Feb;12(2):339-47. doi: 10.1039/c2pp25261a. 1474-905X 10.1039/c2pp25261a 23064410 |
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 |
Royal Society of Chemistry |
publisher.none.fl_str_mv |
Royal Society of Chemistry |
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 |
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RCAAP |
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RCAAP |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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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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1799132215234265088 |