Histidine oxidation photosensitized by pterin: PH dependent mechanism

Autores
Castaño Espinal, Diana Carolina; Oliveros, Esther; Thomas, Andrés Héctor; Lorente, Carolina
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Aromatic pterins accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder, due to the oxidation of tetrahydrobiopterin, the biologically active form of pterins. In this work, we have investigated the ability of pterin, the parent compound of aromatic pterins, to photosensitize the oxidation of histidine in aqueous solutions under UV-A irradiation. Histidine is an α-amino acid with an imidazole functional group, and is frequently present at the active sites of enzymes. The results highlight the role of the pH in controlling the competition between energy and electron transfer mechanisms. It has been previously demonstrated that pterins participate as sensitizers in photosensitized oxidations, both by type I (electron-transfer) and type II mechanisms (singlet oxygen (1O2)). By combining different analytical techniques, we could establish that a type I photooxidation was the prevailing mechanism at acidic pH, although a type II mechanism is also present, but it is more important in alkaline solutions.
Fil: Castaño Espinal, Diana Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Oliveros, Esther. Centre National de la Recherche Scientifique; Francia
Fil: Thomas, Andrés Héctor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Lorente, Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Materia
Histidine
Photosensitization
Pterin
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/48723
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Histidine oxidation photosensitized by pterin: PH dependent mechanismCastaño Espinal, Diana CarolinaOliveros, EstherThomas, Andrés HéctorLorente, CarolinaHistidinePhotosensitizationPterinhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Aromatic pterins accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder, due to the oxidation of tetrahydrobiopterin, the biologically active form of pterins. In this work, we have investigated the ability of pterin, the parent compound of aromatic pterins, to photosensitize the oxidation of histidine in aqueous solutions under UV-A irradiation. Histidine is an α-amino acid with an imidazole functional group, and is frequently present at the active sites of enzymes. The results highlight the role of the pH in controlling the competition between energy and electron transfer mechanisms. It has been previously demonstrated that pterins participate as sensitizers in photosensitized oxidations, both by type I (electron-transfer) and type II mechanisms (singlet oxygen (1O2)). By combining different analytical techniques, we could establish that a type I photooxidation was the prevailing mechanism at acidic pH, although a type II mechanism is also present, but it is more important in alkaline solutions.Fil: Castaño Espinal, Diana Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaFil: Oliveros, Esther. Centre National de la Recherche Scientifique; FranciaFil: Thomas, Andrés Héctor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaFil: Lorente, Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaElsevier Science Sa2015-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/48723Castaño Espinal, Diana Carolina; Oliveros, Esther; Thomas, Andrés Héctor; Lorente, Carolina; Histidine oxidation photosensitized by pterin: PH dependent mechanism; Elsevier Science Sa; Journal of Photochemistry and Photobiology B: Biology; 153; 12-2015; 483-4891011-1344CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotobiol.2015.10.026info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1011134415003553info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:55:09Zoai:ri.conicet.gov.ar:11336/48723instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 09:55:09.716CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Histidine oxidation photosensitized by pterin: PH dependent mechanism
title Histidine oxidation photosensitized by pterin: PH dependent mechanism
spellingShingle Histidine oxidation photosensitized by pterin: PH dependent mechanism
Castaño Espinal, Diana Carolina
Histidine
Photosensitization
Pterin
title_short Histidine oxidation photosensitized by pterin: PH dependent mechanism
title_full Histidine oxidation photosensitized by pterin: PH dependent mechanism
title_fullStr Histidine oxidation photosensitized by pterin: PH dependent mechanism
title_full_unstemmed Histidine oxidation photosensitized by pterin: PH dependent mechanism
title_sort Histidine oxidation photosensitized by pterin: PH dependent mechanism
dc.creator.none.fl_str_mv Castaño Espinal, Diana Carolina
Oliveros, Esther
Thomas, Andrés Héctor
Lorente, Carolina
author Castaño Espinal, Diana Carolina
author_facet Castaño Espinal, Diana Carolina
Oliveros, Esther
Thomas, Andrés Héctor
Lorente, Carolina
author_role author
author2 Oliveros, Esther
Thomas, Andrés Héctor
Lorente, Carolina
author2_role author
author
author
dc.subject.none.fl_str_mv Histidine
Photosensitization
Pterin
topic Histidine
Photosensitization
Pterin
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Aromatic pterins accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder, due to the oxidation of tetrahydrobiopterin, the biologically active form of pterins. In this work, we have investigated the ability of pterin, the parent compound of aromatic pterins, to photosensitize the oxidation of histidine in aqueous solutions under UV-A irradiation. Histidine is an α-amino acid with an imidazole functional group, and is frequently present at the active sites of enzymes. The results highlight the role of the pH in controlling the competition between energy and electron transfer mechanisms. It has been previously demonstrated that pterins participate as sensitizers in photosensitized oxidations, both by type I (electron-transfer) and type II mechanisms (singlet oxygen (1O2)). By combining different analytical techniques, we could establish that a type I photooxidation was the prevailing mechanism at acidic pH, although a type II mechanism is also present, but it is more important in alkaline solutions.
Fil: Castaño Espinal, Diana Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Oliveros, Esther. Centre National de la Recherche Scientifique; Francia
Fil: Thomas, Andrés Héctor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Lorente, Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
description Aromatic pterins accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder, due to the oxidation of tetrahydrobiopterin, the biologically active form of pterins. In this work, we have investigated the ability of pterin, the parent compound of aromatic pterins, to photosensitize the oxidation of histidine in aqueous solutions under UV-A irradiation. Histidine is an α-amino acid with an imidazole functional group, and is frequently present at the active sites of enzymes. The results highlight the role of the pH in controlling the competition between energy and electron transfer mechanisms. It has been previously demonstrated that pterins participate as sensitizers in photosensitized oxidations, both by type I (electron-transfer) and type II mechanisms (singlet oxygen (1O2)). By combining different analytical techniques, we could establish that a type I photooxidation was the prevailing mechanism at acidic pH, although a type II mechanism is also present, but it is more important in alkaline solutions.
publishDate 2015
dc.date.none.fl_str_mv 2015-12
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/48723
Castaño Espinal, Diana Carolina; Oliveros, Esther; Thomas, Andrés Héctor; Lorente, Carolina; Histidine oxidation photosensitized by pterin: PH dependent mechanism; Elsevier Science Sa; Journal of Photochemistry and Photobiology B: Biology; 153; 12-2015; 483-489
1011-1344
CONICET Digital
CONICET
url http://hdl.handle.net/11336/48723
identifier_str_mv Castaño Espinal, Diana Carolina; Oliveros, Esther; Thomas, Andrés Héctor; Lorente, Carolina; Histidine oxidation photosensitized by pterin: PH dependent mechanism; Elsevier Science Sa; Journal of Photochemistry and Photobiology B: Biology; 153; 12-2015; 483-489
1011-1344
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotobiol.2015.10.026
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1011134415003553
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science Sa
publisher.none.fl_str_mv Elsevier Science Sa
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.13397

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