Publicação
N-Pyrenylmethoxycarbonyl phototriggers for the release of serotonin, tryptamine and their biosynthetic precursors
| Resumo: | An evaluation of the pyrenylmethoxycarbonyl group as a photolabile protecting group for the amino function, using neuroactive amines and amino acids as models, was carried out. 1-Hydroxymethylpyrene was reacted with serotonin and tryptamine and their corresponding amino acid precursors, L-5-hydroxytrypthophan and L-trypthophan, in the presence of N,N′-carbonyldiimidazole as carbonylating agent. Photolysis studies were carried out under irradiation at different wavelengths (250, 300, 350 and 419 nm), monitored by HPLC/UV and 1H NMR, and it was found that the carbamate bond between the active molecule and the pyrenylmethyl unit cleaved readily in short irradiation times. The results obtained at 350 nm irradiation are promising for practical purposes (4–20 min). |
|---|---|
| Autores principais: | Fernandes, Maria José G. |
| Outros Autores: | Gonçalves, M. Sameiro T.; Costa, Susana P. G. |
| Assunto: | Phototriggers Caging groups Neurotransmitters Serotonin Pyrene Photolysis |
| Ano: | 2018 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso restrito |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| _version_ | 1866877059536519168 |
|---|---|
| author | Fernandes, Maria José G. |
| author2 | Gonçalves, M. Sameiro T. Costa, Susana P. G. |
| author2_role | author author |
| author_facet | Fernandes, Maria José G. Gonçalves, M. Sameiro T. Costa, Susana P. G. |
| author_role | author |
| contributor_name_str_mv | Universidade do Minho |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Fernandes, Maria José G.\"},{\"Person.name\":\"Gonçalves, M. Sameiro T.\"},{\"Person.name\":\"Costa, Susana P. G.\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Universidade do Minho |
| datacite.creators.creator.creatorName.fl_str_mv | Fernandes, Maria José G. Gonçalves, M. Sameiro T. Costa, Susana P. G. |
| datacite.date.Accepted.fl_str_mv | 2018-01-01T00:00:00Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_16ec |
| datacite.subjects.subject.fl_str_mv | Phototriggers Caging groups Neurotransmitters Serotonin Pyrene Photolysis |
| datacite.titles.title.fl_str_mv | N-Pyrenylmethoxycarbonyl phototriggers for the release of serotonin, tryptamine and their biosynthetic precursors |
| dc.contributor.none.fl_str_mv | Universidade do Minho |
| dc.creator.none.fl_str_mv | Fernandes, Maria José G. Gonçalves, M. Sameiro T. Costa, Susana P. G. |
| dc.date.Accepted.fl_str_mv | 2018-01-01T00:00:00Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | https://hdl.handle.net/1822/57336 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Elsevier |
| dc.rights.cclincense.fl_str_mv | http://creativecommons.org/licenses/by/4.0/ |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_16ec |
| dc.rights.rights.copyright.fl_str_mv | restrictedAccess |
| dc.subject.none.fl_str_mv | Phototriggers Caging groups Neurotransmitters Serotonin Pyrene Photolysis |
| dc.title.fl_str_mv | N-Pyrenylmethoxycarbonyl phototriggers for the release of serotonin, tryptamine and their biosynthetic precursors |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | An evaluation of the pyrenylmethoxycarbonyl group as a photolabile protecting group for the amino function, using neuroactive amines and amino acids as models, was carried out. 1-Hydroxymethylpyrene was reacted with serotonin and tryptamine and their corresponding amino acid precursors, L-5-hydroxytrypthophan and L-trypthophan, in the presence of N,N′-carbonyldiimidazole as carbonylating agent. Photolysis studies were carried out under irradiation at different wavelengths (250, 300, 350 and 419 nm), monitored by HPLC/UV and 1H NMR, and it was found that the carbamate bond between the active molecule and the pyrenylmethyl unit cleaved readily in short irradiation times. The results obtained at 350 nm irradiation are promising for practical purposes (4–20 min). |
| dirty | 0 |
| eu_rights_str_mv | restrictedAccess |
| format | article |
| fulltext.url.fl_str_mv | https://prod-dspace.uminho.pt/bitstreams/7ece7b88-9222-4d9b-a3af-5e69281a43c4/download |
| id | rum_174df5015d3bb4ab67690d8a3d7fec8a |
| identifier.url.fl_str_mv | https://hdl.handle.net/1822/57336 |
| 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:1822/57336 |
| organization_str_mv | urn:organizationAcronym:repositorium |
| person_str_mv | Fernandes, Maria José G. Gonçalves, M. Sameiro T. Costa, Susana P. G. |
| publishDate | 2018 |
| publisher.none.fl_str_mv | Elsevier |
| reponame_str | RepositóriUM - Universidade do Minho |
| repository_id_str | urn:repositoryAcronym:rum |
| service_str_mv | urn:repositoryAcronym:rum |
| spelling | engElsevierporAn evaluation of the pyrenylmethoxycarbonyl group as a photolabile protecting group for the amino function, using neuroactive amines and amino acids as models, was carried out. 1-Hydroxymethylpyrene was reacted with serotonin and tryptamine and their corresponding amino acid precursors, L-5-hydroxytrypthophan and L-trypthophan, in the presence of N,N′-carbonyldiimidazole as carbonylating agent. Photolysis studies were carried out under irradiation at different wavelengths (250, 300, 350 and 419 nm), monitored by HPLC/UV and 1H NMR, and it was found that the carbamate bond between the active molecule and the pyrenylmethyl unit cleaved readily in short irradiation times. The results obtained at 350 nm irradiation are promising for practical purposes (4–20 min).application/pdfporN-Pyrenylmethoxycarbonyl phototriggers for the release of serotonin, tryptamine and their biosynthetic precursorsFernandes, Maria José G.Gonçalves, M. Sameiro T.Costa, Susana P. G.HostingInstitutionOrganizationalUniversidade do Minhoe-mailmailto:repositorium@usdb.uminho.ptrepositorium@usdb.uminho.ptISSNIsPartOf0143-7208DOIIsPartOf10.1016/j.dyepig.2018.01.02120182018-01-01T00:00:00ZHandlehttps://hdl.handle.net/1822/57336http://purl.org/coar/access_right/c_16ecrestricted accessPhototriggersCaging groupsNeurotransmittersSerotoninPyrenePhotolysis807063 bytesliteraturehttp://purl.org/coar/resource_type/c_6501journal article2018http://creativecommons.org/licenses/by/4.0/restrictedAccesshttp://purl.org/coar/access_right/c_16ecapplication/pdffulltexthttps://prod-dspace.uminho.pt/bitstreams/7ece7b88-9222-4d9b-a3af-5e69281a43c4/download |
| spellingShingle | N-Pyrenylmethoxycarbonyl phototriggers for the release of serotonin, tryptamine and their biosynthetic precursors Fernandes, Maria José G. Phototriggers Caging groups Neurotransmitters Serotonin Pyrene Photolysis |
| status | SINGLETON |
| subject.fl_str_mv | Phototriggers Caging groups Neurotransmitters Serotonin Pyrene Photolysis |
| title | N-Pyrenylmethoxycarbonyl phototriggers for the release of serotonin, tryptamine and their biosynthetic precursors |
| title_full | N-Pyrenylmethoxycarbonyl phototriggers for the release of serotonin, tryptamine and their biosynthetic precursors |
| title_fullStr | N-Pyrenylmethoxycarbonyl phototriggers for the release of serotonin, tryptamine and their biosynthetic precursors |
| title_full_unstemmed | N-Pyrenylmethoxycarbonyl phototriggers for the release of serotonin, tryptamine and their biosynthetic precursors |
| title_short | N-Pyrenylmethoxycarbonyl phototriggers for the release of serotonin, tryptamine and their biosynthetic precursors |
| title_sort | N-Pyrenylmethoxycarbonyl phototriggers for the release of serotonin, tryptamine and their biosynthetic precursors |
| topic | Phototriggers Caging groups Neurotransmitters Serotonin Pyrene Photolysis |
| topic_facet | Phototriggers Caging groups Neurotransmitters Serotonin Pyrene Photolysis |
| url | https://hdl.handle.net/1822/57336 |
| visible | 1 |