Oxidation of Tyrosine Photoinduced by Pterin in Aqueous Solution
- Autores
- Castaño Espinal, Diana Carolina; Dantola, Maria Laura; Oliveros, Esther; Thomas, Andrés Héctor; Lorente, Carolina
- Año de publicación
- 2013
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- Pterins, heterocyclic compounds widespread in biological systems, accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder. Pterins have been previously identified as good photosensitizers under UV-A irradiation. In this work, we have investigated the ability of pterin (Ptr), the parent compound of oxidized pterins, to photosensitize the oxidation of tyrosine (Tyr) in aqueous solutions. Tyr is an important target in the study of the photodynamic effects of UV-A radiation because it is oxidized by singlet oxygen (1O2) and plays a key role in polymerization and cross-linking of proteins. Steady UV-A irradiation of solutions containing Ptr and Tyr led to the consumption of Tyr and dissolved O2, whereas the Ptr concentration remained unchanged. Concomitantly, hydrogen peroxide (H2O2) was produced. By combining different analytical techniques, we could establish that the mechanism of the photosensitized process involves an electron transfer from Tyr to the triplet excited state of Ptr. Mass spectrometry, chromatography and fluorescence were used to analyze the photoproducts. In particular, oxygenated and dimeric compounds were identified.
Fil: Castaño Espinal, Diana Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Dantola, Maria Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Oliveros, Esther. Universite Paul Sabatier; Francia
Fil: Thomas, Andrés Héctor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Lorente, Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina - Materia
-
Tyrosine
Pterin
Photosensitization
Electron Transfer - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/4784
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Oxidation of Tyrosine Photoinduced by Pterin in Aqueous SolutionCastaño Espinal, Diana CarolinaDantola, Maria LauraOliveros, EstherThomas, Andrés HéctorLorente, CarolinaTyrosinePterinPhotosensitizationElectron Transferhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Pterins, heterocyclic compounds widespread in biological systems, accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder. Pterins have been previously identified as good photosensitizers under UV-A irradiation. In this work, we have investigated the ability of pterin (Ptr), the parent compound of oxidized pterins, to photosensitize the oxidation of tyrosine (Tyr) in aqueous solutions. Tyr is an important target in the study of the photodynamic effects of UV-A radiation because it is oxidized by singlet oxygen (1O2) and plays a key role in polymerization and cross-linking of proteins. Steady UV-A irradiation of solutions containing Ptr and Tyr led to the consumption of Tyr and dissolved O2, whereas the Ptr concentration remained unchanged. Concomitantly, hydrogen peroxide (H2O2) was produced. By combining different analytical techniques, we could establish that the mechanism of the photosensitized process involves an electron transfer from Tyr to the triplet excited state of Ptr. Mass spectrometry, chromatography and fluorescence were used to analyze the photoproducts. In particular, oxygenated and dimeric compounds were identified.Fil: Castaño Espinal, Diana Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaFil: Dantola, Maria Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaFil: Oliveros, Esther. Universite Paul Sabatier; FranciaFil: Thomas, Andrés Héctor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaFil: Lorente, Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaWiley2013-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/4784Castaño Espinal, Diana Carolina; Dantola, Maria Laura; Oliveros, Esther; Thomas, Andrés Héctor; Lorente, Carolina; Oxidation of Tyrosine Photoinduced by Pterin in Aqueous Solution; Wiley; Photochemistry and Photobiology; 89; 6; 5-2013; 1448-14550031-8655enginfo:eu-repo/semantics/altIdentifier/doi/10.1111/php.12099info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/wol1/doi/10.1111/php.12099/abstractinfo:eu-repo/semantics/altIdentifier/issn/0031-8655info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:09:59Zoai:ri.conicet.gov.ar:11336/4784instacron: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 10:09:59.694CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Oxidation of Tyrosine Photoinduced by Pterin in Aqueous Solution |
title |
Oxidation of Tyrosine Photoinduced by Pterin in Aqueous Solution |
spellingShingle |
Oxidation of Tyrosine Photoinduced by Pterin in Aqueous Solution Castaño Espinal, Diana Carolina Tyrosine Pterin Photosensitization Electron Transfer |
title_short |
Oxidation of Tyrosine Photoinduced by Pterin in Aqueous Solution |
title_full |
Oxidation of Tyrosine Photoinduced by Pterin in Aqueous Solution |
title_fullStr |
Oxidation of Tyrosine Photoinduced by Pterin in Aqueous Solution |
title_full_unstemmed |
Oxidation of Tyrosine Photoinduced by Pterin in Aqueous Solution |
title_sort |
Oxidation of Tyrosine Photoinduced by Pterin in Aqueous Solution |
dc.creator.none.fl_str_mv |
Castaño Espinal, Diana Carolina Dantola, Maria Laura Oliveros, Esther Thomas, Andrés Héctor Lorente, Carolina |
author |
Castaño Espinal, Diana Carolina |
author_facet |
Castaño Espinal, Diana Carolina Dantola, Maria Laura Oliveros, Esther Thomas, Andrés Héctor Lorente, Carolina |
author_role |
author |
author2 |
Dantola, Maria Laura Oliveros, Esther Thomas, Andrés Héctor Lorente, Carolina |
author2_role |
author author author author |
dc.subject.none.fl_str_mv |
Tyrosine Pterin Photosensitization Electron Transfer |
topic |
Tyrosine Pterin Photosensitization Electron Transfer |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
Pterins, heterocyclic compounds widespread in biological systems, accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder. Pterins have been previously identified as good photosensitizers under UV-A irradiation. In this work, we have investigated the ability of pterin (Ptr), the parent compound of oxidized pterins, to photosensitize the oxidation of tyrosine (Tyr) in aqueous solutions. Tyr is an important target in the study of the photodynamic effects of UV-A radiation because it is oxidized by singlet oxygen (1O2) and plays a key role in polymerization and cross-linking of proteins. Steady UV-A irradiation of solutions containing Ptr and Tyr led to the consumption of Tyr and dissolved O2, whereas the Ptr concentration remained unchanged. Concomitantly, hydrogen peroxide (H2O2) was produced. By combining different analytical techniques, we could establish that the mechanism of the photosensitized process involves an electron transfer from Tyr to the triplet excited state of Ptr. Mass spectrometry, chromatography and fluorescence were used to analyze the photoproducts. In particular, oxygenated and dimeric compounds were identified. Fil: Castaño Espinal, Diana Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina Fil: Dantola, Maria Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina Fil: Oliveros, Esther. Universite Paul Sabatier; Francia Fil: Thomas, Andrés Héctor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina Fil: Lorente, Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina |
description |
Pterins, heterocyclic compounds widespread in biological systems, accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder. Pterins have been previously identified as good photosensitizers under UV-A irradiation. In this work, we have investigated the ability of pterin (Ptr), the parent compound of oxidized pterins, to photosensitize the oxidation of tyrosine (Tyr) in aqueous solutions. Tyr is an important target in the study of the photodynamic effects of UV-A radiation because it is oxidized by singlet oxygen (1O2) and plays a key role in polymerization and cross-linking of proteins. Steady UV-A irradiation of solutions containing Ptr and Tyr led to the consumption of Tyr and dissolved O2, whereas the Ptr concentration remained unchanged. Concomitantly, hydrogen peroxide (H2O2) was produced. By combining different analytical techniques, we could establish that the mechanism of the photosensitized process involves an electron transfer from Tyr to the triplet excited state of Ptr. Mass spectrometry, chromatography and fluorescence were used to analyze the photoproducts. In particular, oxygenated and dimeric compounds were identified. |
publishDate |
2013 |
dc.date.none.fl_str_mv |
2013-05 |
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/11336/4784 Castaño Espinal, Diana Carolina; Dantola, Maria Laura; Oliveros, Esther; Thomas, Andrés Héctor; Lorente, Carolina; Oxidation of Tyrosine Photoinduced by Pterin in Aqueous Solution; Wiley; Photochemistry and Photobiology; 89; 6; 5-2013; 1448-1455 0031-8655 |
url |
http://hdl.handle.net/11336/4784 |
identifier_str_mv |
Castaño Espinal, Diana Carolina; Dantola, Maria Laura; Oliveros, Esther; Thomas, Andrés Héctor; Lorente, Carolina; Oxidation of Tyrosine Photoinduced by Pterin in Aqueous Solution; Wiley; Photochemistry and Photobiology; 89; 6; 5-2013; 1448-1455 0031-8655 |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/doi/10.1111/php.12099 info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/wol1/doi/10.1111/php.12099/abstract info:eu-repo/semantics/altIdentifier/issn/0031-8655 |
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 application/pdf application/pdf application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
Wiley |
publisher.none.fl_str_mv |
Wiley |
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reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
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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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