Publicação
Aminobenzocoumarinylmehtyl esters as photoactive precursors for the release of butyric acid
| Resumo: | The evaluation of the photorelease of a carboxylic acid drug, using butyric acid as a representative model, was carried out by using 7-amino-4-chloromethyl-2-oxo-2Hnaphtho[1,2-b] pyran, an aminobenzocoumarin, and its mono- and di-methylated or ethylated derivatives. This study was intended to improve the release of butyric acid from benzocoumarins by the addition of an amino group to the heterocycle by applying the knowledge of second-generation coumarinylmethyl-based photoremovable protecting groups. Photolysis studies were performed on the resultant ester cages by irradiation in a photochemical reactor at 254, 300, 350 and 419 nm, using methanol/HEPES buffer 80:20 solutions as solvent. The data obtained showed that these new fluorescent aminobenzocoumarins are superior to all the previously tested benzocoumarins with the same or different ring fusions. As well as the photolysis, the photophysics of the compounds were characterised by both steady state and time-resolved methods. |
|---|---|
| Autores principais: | Soares, Ana M. S. |
| Outros Autores: | Hungerford, Graham; Costa, Susana P. G.; Gonçalves, M. Sameiro T. |
| Assunto: | Butyric acid Benzocoumarin Ciências Naturais::Ciências Químicas |
| Ano: | 2015 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso restrito |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| _version_ | 1867438731345002496 |
|---|---|
| author | Soares, Ana M. S. |
| author2 | Hungerford, Graham Costa, Susana P. G. Gonçalves, M. Sameiro T. |
| author2_role | author author author |
| author_facet | Soares, Ana M. S. Hungerford, Graham Costa, Susana P. G. Gonçalves, M. Sameiro T. |
| author_role | author |
| contributor_name_str_mv | RepositóriUM - Universidade do Minho |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Soares, Ana M. S.\"},{\"Person.name\":\"Hungerford, Graham\"},{\"Person.name\":\"Costa, Susana P. G.\"},{\"Person.name\":\"Gonçalves, M. Sameiro T.\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | RepositóriUM - Universidade do Minho |
| datacite.creators.creator.creatorName.fl_str_mv | Soares, Ana M. S. Hungerford, Graham Costa, Susana P. G. Gonçalves, M. Sameiro T. |
| datacite.date.Accepted.fl_str_mv | 2015-07-01T00:00:00Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_16ec |
| datacite.subjects.subject.fl_str_mv | Butyric acid Benzocoumarin Ciências Naturais::Ciências Químicas |
| datacite.titles.title.fl_str_mv | Aminobenzocoumarinylmehtyl esters as photoactive precursors for the release of butyric acid |
| dc.contributor.none.fl_str_mv | RepositóriUM - Universidade do Minho |
| dc.creator.none.fl_str_mv | Soares, Ana M. S. Hungerford, Graham Costa, Susana P. G. Gonçalves, M. Sameiro T. |
| dc.date.Accepted.fl_str_mv | 2015-07-01T00:00:00Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | https://hdl.handle.net/1822/39071 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Royal Society of Chemistry |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_16ec |
| dc.subject.none.fl_str_mv | Butyric acid Benzocoumarin Ciências Naturais::Ciências Químicas |
| dc.title.fl_str_mv | Aminobenzocoumarinylmehtyl esters as photoactive precursors for the release of butyric acid |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | The evaluation of the photorelease of a carboxylic acid drug, using butyric acid as a representative model, was carried out by using 7-amino-4-chloromethyl-2-oxo-2Hnaphtho[1,2-b] pyran, an aminobenzocoumarin, and its mono- and di-methylated or ethylated derivatives. This study was intended to improve the release of butyric acid from benzocoumarins by the addition of an amino group to the heterocycle by applying the knowledge of second-generation coumarinylmethyl-based photoremovable protecting groups. Photolysis studies were performed on the resultant ester cages by irradiation in a photochemical reactor at 254, 300, 350 and 419 nm, using methanol/HEPES buffer 80:20 solutions as solvent. The data obtained showed that these new fluorescent aminobenzocoumarins are superior to all the previously tested benzocoumarins with the same or different ring fusions. As well as the photolysis, the photophysics of the compounds were characterised by both steady state and time-resolved methods. |
| dirty | 0 |
| eu_rights_str_mv | restrictedAccess |
| format | article |
| fulltext.url.fl_str_mv | https://repositorium.uminho.pt/bitstreams/2111e579-8a53-4746-b483-cf9794233d0a/download |
| id | rum_5dd2e26f942ec00e55ce88eb3a3d1ce0 |
| identifier.url.fl_str_mv | https://hdl.handle.net/1822/39071 |
| instacron_str | repositorium |
| institution | Universidade do Minho |
| instname_str | Universidade do Minho |
| language | eng |
| network_acronym_str | rum |
| network_name_str | RepositóriUM - Universidade do Minho |
| oai_identifier_str | oai:repositorium.uminho.pt:1822/39071 |
| organization_str_mv | urn:organizationAcronym:repositorium |
| person_str_mv | Soares, Ana M. S. Hungerford, Graham Costa, Susana P. G. Gonçalves, M. Sameiro T. |
| publishDate | 2015 |
| publisher.none.fl_str_mv | Royal Society of Chemistry |
| reponame_str | RepositóriUM - Universidade do Minho |
| repository_id_str | urn:repositoryAcronym:rum |
| service_str_mv | urn:repositoryAcronym:rum |
| spelling | engRoyal Society of ChemistryporThe evaluation of the photorelease of a carboxylic acid drug, using butyric acid as a representative model, was carried out by using 7-amino-4-chloromethyl-2-oxo-2Hnaphtho[1,2-b] pyran, an aminobenzocoumarin, and its mono- and di-methylated or ethylated derivatives. This study was intended to improve the release of butyric acid from benzocoumarins by the addition of an amino group to the heterocycle by applying the knowledge of second-generation coumarinylmethyl-based photoremovable protecting groups. Photolysis studies were performed on the resultant ester cages by irradiation in a photochemical reactor at 254, 300, 350 and 419 nm, using methanol/HEPES buffer 80:20 solutions as solvent. The data obtained showed that these new fluorescent aminobenzocoumarins are superior to all the previously tested benzocoumarins with the same or different ring fusions. As well as the photolysis, the photophysics of the compounds were characterised by both steady state and time-resolved methods.application/pdfporAminobenzocoumarinylmehtyl esters as photoactive precursors for the release of butyric acidSoares, Ana M. S.Hungerford, GrahamCosta, Susana P. G.Gonçalves, M. Sameiro T.HostingInstitutionOrganizationalRepositóriUM - Universidade do Minhoe-mailmailto:repositorium@usdb.uminho.ptrepositorium@usdb.uminho.ptCITATIONAna M. S. Soares, Graham Hungerford, Susana P. G. Costa, M. Sameiro T. Gonçalves, N. J. Chem., 2015, 39, 7227-7233.ISSNIsPartOf1144-0546DOIIsPartOf10.1039/c5nj00699f2015-072015-07-01T00:00:00ZHandlehttps://hdl.handle.net/1822/39071http://purl.org/coar/access_right/c_16ecrestricted accessButyric acidBenzocoumarinhttp://www.oecd.org/science/inno/38235147.pdfFields of Science and Technology (FOS)Ciências Naturais::Ciências Químicas1940785 bytesliteraturehttp://purl.org/coar/resource_type/c_6501journal articlehttp://purl.org/coar/access_right/c_16ecapplication/pdffulltexthttps://repositorium.uminho.pt/bitstreams/2111e579-8a53-4746-b483-cf9794233d0a/download |
| spellingShingle | Aminobenzocoumarinylmehtyl esters as photoactive precursors for the release of butyric acid Soares, Ana M. S. Butyric acid Benzocoumarin Ciências Naturais::Ciências Químicas |
| status | SINGLETON |
| subject.fl_str_mv | Butyric acid Benzocoumarin |
| subject.other.fl_str_mv | Ciências Naturais::Ciências Químicas |
| title | Aminobenzocoumarinylmehtyl esters as photoactive precursors for the release of butyric acid |
| title_full | Aminobenzocoumarinylmehtyl esters as photoactive precursors for the release of butyric acid |
| title_fullStr | Aminobenzocoumarinylmehtyl esters as photoactive precursors for the release of butyric acid |
| title_full_unstemmed | Aminobenzocoumarinylmehtyl esters as photoactive precursors for the release of butyric acid |
| title_short | Aminobenzocoumarinylmehtyl esters as photoactive precursors for the release of butyric acid |
| title_sort | Aminobenzocoumarinylmehtyl esters as photoactive precursors for the release of butyric acid |
| topic | Butyric acid Benzocoumarin Ciências Naturais::Ciências Químicas |
| topic_facet | Butyric acid Benzocoumarin Ciências Naturais::Ciências Químicas |
| url | https://hdl.handle.net/1822/39071 |
| visible | 1 |