Degradation of alfa-melanocyte-stimulating hormone photosensitized by pterin

Autores
Castaño Espinal, Diana Carolina; Lorente, Carolina; Martins Froment, Nathalie; Oliveros, Esther; Thomas, Andrés Héctor
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Oxidized pterins, efficient photosensitizers under UV-A irradiation, accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder. In this work, we have investigated the ability of pterin (Ptr), the parent compound of oxidized pterins, to photosensitize the oxidation of the peptide α-melanocyte-stimulating hormone (α-MSH), which stimulates the production and release of melanin by melanocytes in skin and hair. Our results showed that Ptr is able to photoinduce the degradation of α-MSH upon UV-A irradiation and that the reaction is initiated by an electron transfer from the peptide to the triplet excited state of Ptr. The photosensitized process produces chemical changes in at least two different amino acid residues: tryptophan and tyrosine (Tyr). It was shown that α-MSH undergoes dimerization and oxidation, the former process taking place after the formation of Tyr radicals. The present findings are analyzed in the context of the general behavior of pterins as photosensitizers and the biological implications are discussed.
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. Universidad Nacional de La Plata; Argentina
Fil: Lorente, Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina. Universidad Nacional de La Plata; Argentina
Fil: Martins Froment, Nathalie. Université de Toulouse II. Service Commun de Spectrométrie de Masse; Francia
Fil: Oliveros, Esther. Université de Toulouse II; 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. Universidad Nacional de La Plata; Argentina
Materia
Photosensitization
Pterin
Melanocyte-Stimulating Hormone
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:11336/5130
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Degradation of alfa-melanocyte-stimulating hormone photosensitized by pterinCastaño Espinal, Diana CarolinaLorente, CarolinaMartins Froment, NathalieOliveros, EstherThomas, Andrés HéctorPhotosensitizationPterinMelanocyte-Stimulating Hormonehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Oxidized pterins, efficient photosensitizers under UV-A irradiation, accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder. In this work, we have investigated the ability of pterin (Ptr), the parent compound of oxidized pterins, to photosensitize the oxidation of the peptide α-melanocyte-stimulating hormone (α-MSH), which stimulates the production and release of melanin by melanocytes in skin and hair. Our results showed that Ptr is able to photoinduce the degradation of α-MSH upon UV-A irradiation and that the reaction is initiated by an electron transfer from the peptide to the triplet excited state of Ptr. The photosensitized process produces chemical changes in at least two different amino acid residues: tryptophan and tyrosine (Tyr). It was shown that α-MSH undergoes dimerization and oxidation, the former process taking place after the formation of Tyr radicals. The present findings are analyzed in the context of the general behavior of pterins as photosensitizers and the biological implications are discussed.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. Universidad Nacional de La Plata; ArgentinaFil: Lorente, Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina. Universidad Nacional de La Plata; ArgentinaFil: Martins Froment, Nathalie. Université de Toulouse II. Service Commun de Spectrométrie de Masse; FranciaFil: Oliveros, Esther. Université de Toulouse II; FranciaFil: Thomas, Andrés Héctor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina. Universidad Nacional de La Plata; ArgentinaRoyal Society of Chemistry2014-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/5130Castaño Espinal, Diana Carolina; Lorente, Carolina; Martins Froment, Nathalie; Oliveros, Esther; Thomas, Andrés Héctor; Degradation of alfa-melanocyte-stimulating hormone photosensitized by pterin; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 12; 23; 4-2014; 3877-38861477-0520enginfo:eu-repo/semantics/altIdentifier/doi/10.1039/c4ob00434einfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2014/OB/c4ob00434e#!divAbstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:58:44Zoai:ri.conicet.gov.ar:11336/5130instacron: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:34982025-09-29 09:58:44.863CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Degradation of alfa-melanocyte-stimulating hormone photosensitized by pterin
title Degradation of alfa-melanocyte-stimulating hormone photosensitized by pterin
spellingShingle Degradation of alfa-melanocyte-stimulating hormone photosensitized by pterin
Castaño Espinal, Diana Carolina
Photosensitization
Pterin
Melanocyte-Stimulating Hormone
title_short Degradation of alfa-melanocyte-stimulating hormone photosensitized by pterin
title_full Degradation of alfa-melanocyte-stimulating hormone photosensitized by pterin
title_fullStr Degradation of alfa-melanocyte-stimulating hormone photosensitized by pterin
title_full_unstemmed Degradation of alfa-melanocyte-stimulating hormone photosensitized by pterin
title_sort Degradation of alfa-melanocyte-stimulating hormone photosensitized by pterin
dc.creator.none.fl_str_mv Castaño Espinal, Diana Carolina
Lorente, Carolina
Martins Froment, Nathalie
Oliveros, Esther
Thomas, Andrés Héctor
author Castaño Espinal, Diana Carolina
author_facet Castaño Espinal, Diana Carolina
Lorente, Carolina
Martins Froment, Nathalie
Oliveros, Esther
Thomas, Andrés Héctor
author_role author
author2 Lorente, Carolina
Martins Froment, Nathalie
Oliveros, Esther
Thomas, Andrés Héctor
author2_role author
author
author
author
dc.subject.none.fl_str_mv Photosensitization
Pterin
Melanocyte-Stimulating Hormone
topic Photosensitization
Pterin
Melanocyte-Stimulating Hormone
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Oxidized pterins, efficient photosensitizers under UV-A irradiation, accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder. In this work, we have investigated the ability of pterin (Ptr), the parent compound of oxidized pterins, to photosensitize the oxidation of the peptide α-melanocyte-stimulating hormone (α-MSH), which stimulates the production and release of melanin by melanocytes in skin and hair. Our results showed that Ptr is able to photoinduce the degradation of α-MSH upon UV-A irradiation and that the reaction is initiated by an electron transfer from the peptide to the triplet excited state of Ptr. The photosensitized process produces chemical changes in at least two different amino acid residues: tryptophan and tyrosine (Tyr). It was shown that α-MSH undergoes dimerization and oxidation, the former process taking place after the formation of Tyr radicals. The present findings are analyzed in the context of the general behavior of pterins as photosensitizers and the biological implications are discussed.
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. Universidad Nacional de La Plata; Argentina
Fil: Lorente, Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina. Universidad Nacional de La Plata; Argentina
Fil: Martins Froment, Nathalie. Université de Toulouse II. Service Commun de Spectrométrie de Masse; Francia
Fil: Oliveros, Esther. Université de Toulouse II; 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. Universidad Nacional de La Plata; Argentina
description Oxidized pterins, efficient photosensitizers under UV-A irradiation, accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder. In this work, we have investigated the ability of pterin (Ptr), the parent compound of oxidized pterins, to photosensitize the oxidation of the peptide α-melanocyte-stimulating hormone (α-MSH), which stimulates the production and release of melanin by melanocytes in skin and hair. Our results showed that Ptr is able to photoinduce the degradation of α-MSH upon UV-A irradiation and that the reaction is initiated by an electron transfer from the peptide to the triplet excited state of Ptr. The photosensitized process produces chemical changes in at least two different amino acid residues: tryptophan and tyrosine (Tyr). It was shown that α-MSH undergoes dimerization and oxidation, the former process taking place after the formation of Tyr radicals. The present findings are analyzed in the context of the general behavior of pterins as photosensitizers and the biological implications are discussed.
publishDate 2014
dc.date.none.fl_str_mv 2014-04
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/11336/5130
Castaño Espinal, Diana Carolina; Lorente, Carolina; Martins Froment, Nathalie; Oliveros, Esther; Thomas, Andrés Héctor; Degradation of alfa-melanocyte-stimulating hormone photosensitized by pterin; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 12; 23; 4-2014; 3877-3886
1477-0520
url http://hdl.handle.net/11336/5130
identifier_str_mv Castaño Espinal, Diana Carolina; Lorente, Carolina; Martins Froment, Nathalie; Oliveros, Esther; Thomas, Andrés Héctor; Degradation of alfa-melanocyte-stimulating hormone photosensitized by pterin; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 12; 23; 4-2014; 3877-3886
1477-0520
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/c4ob00434e
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2014/OB/c4ob00434e#!divAbstract
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 Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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 13.070432

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