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Photolytic release of bioactive carboxylic acids from fused pyran conjugates

Detalhes bibliográficos
Autor(a) principal: Conceição, Rafaela
Data de Publicação: 2018
Outros Autores: Hungerford, Graham, Costa, Susana P. G., Gonçalves, M. Sameiro T.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
Texto Completo: https://hdl.handle.net/1822/49045
Resumo: New ester cages bearing the coumarin (2H-benzopyran-2-one) skeleton with extended π-systems as phototriggers, for glycine and β-alanine, as models of carboxylic acid bifunctional molecules with biological relevance, were evaluated under photolysis conditions at 254, 300, 350 and 419 nm of irradiation in a RPR-100 photochemical reactor. The processes were followed by HPLC-UV detection and 1H NMR with collection of kinetic data. The results showed a correlation between the photolysis efficiency and the increasing extension of the conjugation for both glycine and β-alanine, showing that the 7-aminocoumarin afforded the best results at all wavelengths tested. From a study of the time-resolved fluorescence behaviour, these compounds were also found to exhibit more complex fluorescence decay kinetics. This was attributed to the presence of conjugated and non-conjugated coumarin species.
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spelling Photolytic release of bioactive carboxylic acids from fused pyran conjugatesPhototriggersCaging groupsNeurotransmittersCoumarinsPhotolysisCiências Naturais::Ciências QuímicasScience & TechnologyNew ester cages bearing the coumarin (2H-benzopyran-2-one) skeleton with extended π-systems as phototriggers, for glycine and β-alanine, as models of carboxylic acid bifunctional molecules with biological relevance, were evaluated under photolysis conditions at 254, 300, 350 and 419 nm of irradiation in a RPR-100 photochemical reactor. The processes were followed by HPLC-UV detection and 1H NMR with collection of kinetic data. The results showed a correlation between the photolysis efficiency and the increasing extension of the conjugation for both glycine and β-alanine, showing that the 7-aminocoumarin afforded the best results at all wavelengths tested. From a study of the time-resolved fluorescence behaviour, these compounds were also found to exhibit more complex fluorescence decay kinetics. This was attributed to the presence of conjugated and non-conjugated coumarin species.Thanks are due to Fundação para a Ciência e Tecnologia (FCT) and FEDER (European Fund for Regional Development)-COMPETE-QREN-EU for financial support through the Chemistry Research Centre of the University of Minho (Ref. UID/QUI/00686/2013 and UID/ QUI/0686/2016). The NMR spectrometer Bruker Avance III 400 is part of the National NMR Network and was purchased within the framework of the National Program for Scientific Re-equipment, contract REDE/1517/RMN/2005 with funds from POCI 2010 (FEDER) and FCT.info:eu-repo/semantics/publishedVersionElsevierUniversidade do MinhoConceição, RafaelaHungerford, GrahamCosta, Susana P. G.Gonçalves, M. Sameiro T.20182018-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/1822/49045engR . Conceição, G. Hungerford, S. P. G. Costa, M. S. T. Gonçalves, “Photolytic release of bioactive carboxylic acids from fused pyran conjugates”, Dyes Pigments, 2018, 148, 368-379.0143-72081873-374310.1016/j.dyepig.2017.09.023https://doi.org/10.1016/j.dyepig.2017.09.023info:eu-repo/semantics/openAccessreponame:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiainstacron:RCAAP2025-04-12T04:56:05Zoai:repositorium.sdum.uminho.pt:1822/49045Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireinfo@rcaap.ptopendoar:https://opendoar.ac.uk/repository/71602025-05-28T15:47:43.652923Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiafalse
dc.title.none.fl_str_mv Photolytic release of bioactive carboxylic acids from fused pyran conjugates
title Photolytic release of bioactive carboxylic acids from fused pyran conjugates
spellingShingle Photolytic release of bioactive carboxylic acids from fused pyran conjugates
Conceição, Rafaela
Phototriggers
Caging groups
Neurotransmitters
Coumarins
Photolysis
Ciências Naturais::Ciências Químicas
Science & Technology
title_short Photolytic release of bioactive carboxylic acids from fused pyran conjugates
title_full Photolytic release of bioactive carboxylic acids from fused pyran conjugates
title_fullStr Photolytic release of bioactive carboxylic acids from fused pyran conjugates
title_full_unstemmed Photolytic release of bioactive carboxylic acids from fused pyran conjugates
title_sort Photolytic release of bioactive carboxylic acids from fused pyran conjugates
author Conceição, Rafaela
author_facet Conceição, Rafaela
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 Conceição, Rafaela
Hungerford, Graham
Costa, Susana P. G.
Gonçalves, M. Sameiro T.
dc.subject.por.fl_str_mv Phototriggers
Caging groups
Neurotransmitters
Coumarins
Photolysis
Ciências Naturais::Ciências Químicas
Science & Technology
topic Phototriggers
Caging groups
Neurotransmitters
Coumarins
Photolysis
Ciências Naturais::Ciências Químicas
Science & Technology
description New ester cages bearing the coumarin (2H-benzopyran-2-one) skeleton with extended π-systems as phototriggers, for glycine and β-alanine, as models of carboxylic acid bifunctional molecules with biological relevance, were evaluated under photolysis conditions at 254, 300, 350 and 419 nm of irradiation in a RPR-100 photochemical reactor. The processes were followed by HPLC-UV detection and 1H NMR with collection of kinetic data. The results showed a correlation between the photolysis efficiency and the increasing extension of the conjugation for both glycine and β-alanine, showing that the 7-aminocoumarin afforded the best results at all wavelengths tested. From a study of the time-resolved fluorescence behaviour, these compounds were also found to exhibit more complex fluorescence decay kinetics. This was attributed to the presence of conjugated and non-conjugated coumarin species.
publishDate 2018
dc.date.none.fl_str_mv 2018
2018-01-01T00:00:00Z
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 https://hdl.handle.net/1822/49045
url https://hdl.handle.net/1822/49045
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv R . Conceição, G. Hungerford, S. P. G. Costa, M. S. T. Gonçalves, “Photolytic release of bioactive carboxylic acids from fused pyran conjugates”, Dyes Pigments, 2018, 148, 368-379.
0143-7208
1873-3743
10.1016/j.dyepig.2017.09.023
https://doi.org/10.1016/j.dyepig.2017.09.023
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:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
instacron:RCAAP
instname_str FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
instacron_str RCAAP
institution RCAAP
reponame_str Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
collection Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
repository.name.fl_str_mv Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
repository.mail.fl_str_mv info@rcaap.pt
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