Tryptophan Oxidation Photosensitizided by Pterin

Autores
Thomas, Andrés Héctor; Serrano, Mariana Paula; Rahal, Virginie; Vicendo, Patricia; Claparols, Catherine; Oliveros, Esther; Lorente, Carolina
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Pterins are normal components of cells and they have been previously identified as good photosensitizers under UV-A irradiation, inducing DNA damage and oxidation of nucleotides. In this work, we have investigated the ability of pterin (Ptr), the parent compound of oxidized pterins, to photosensitize the oxidation of another class of biomolecules, aminoacids, using tryptophan (Trp) as a model compound.  Irradiation of Ptr in the UV-A spectral range (350 nm) in aerated aqueous solutions containing Trp led to the consumption of the latter, whereas the Ptr concentration remained unchanged. Concomitantly, hydrogen peroxide (H2O2) was produced. Although Ptr is a singlet oxygen (1O2) sensitizer, the degradation of Trp was inhibited in O2-saturated solutions, indicating that a 1O2-mediated process (Type II oxidation) was not an important pathway leading to Trp oxidation. By combining different analytical techniques, we could establish that a Type I photooxidation was the prevailing mechanism, initiated by an electron transfer from the Trp molecule to the Ptr triplet excited state yielding the corresponding radical ions (Trp.+/Trp(-H). and Ptr.-). The Trp reaction products that could be identified by UPLC-mass spectrometry are in agreement with this conclusion.
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: Serrano, Mariana Paula. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Rahal, Virginie. Universite Paul Sabatier; Francia
Fil: Vicendo, Patricia. Universite Paul Sabatier; Francia
Fil: Claparols, Catherine. Universite Paul Sabatier; Francia
Fil: Oliveros, Esther. Universite Paul Sabatier; Francia
Fil: Lorente, Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Materia
Photosensitization
Tryptophan
Pterin
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/4817
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/4817
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network_name_str CONICET Digital (CONICET)
spelling Tryptophan Oxidation Photosensitizided by PterinThomas, Andrés HéctorSerrano, Mariana PaulaRahal, VirginieVicendo, PatriciaClaparols, CatherineOliveros, EstherLorente, CarolinaPhotosensitizationTryptophanPterinhttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Pterins are normal components of cells and they have been previously identified as good photosensitizers under UV-A irradiation, inducing DNA damage and oxidation of nucleotides. In this work, we have investigated the ability of pterin (Ptr), the parent compound of oxidized pterins, to photosensitize the oxidation of another class of biomolecules, aminoacids, using tryptophan (Trp) as a model compound.  Irradiation of Ptr in the UV-A spectral range (350 nm) in aerated aqueous solutions containing Trp led to the consumption of the latter, whereas the Ptr concentration remained unchanged. Concomitantly, hydrogen peroxide (H2O2) was produced. Although Ptr is a singlet oxygen (1O2) sensitizer, the degradation of Trp was inhibited in O2-saturated solutions, indicating that a 1O2-mediated process (Type II oxidation) was not an important pathway leading to Trp oxidation. By combining different analytical techniques, we could establish that a Type I photooxidation was the prevailing mechanism, initiated by an electron transfer from the Trp molecule to the Ptr triplet excited state yielding the corresponding radical ions (Trp.+/Trp(-H). and Ptr.-). The Trp reaction products that could be identified by UPLC-mass spectrometry are in agreement with this conclusion.Fil: Thomas, Andrés Héctor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaFil: Serrano, Mariana Paula. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaFil: Rahal, Virginie. Universite Paul Sabatier; FranciaFil: Vicendo, Patricia. Universite Paul Sabatier; FranciaFil: Claparols, Catherine. Universite Paul Sabatier; FranciaFil: Oliveros, Esther. Universite Paul Sabatier; FranciaFil: Lorente, Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaElsevier2013-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/4817Thomas, Andrés Héctor; Serrano, Mariana Paula; Rahal, Virginie; Vicendo, Patricia; Claparols, Catherine; et al.; Tryptophan Oxidation Photosensitizided by Pterin; Elsevier; Free Radical Biology and Medicine; 63; 5-2013; 467–4750891-5849enginfo:eu-repo/semantics/altIdentifier/pmid/PMID: 23747929info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0891584913002724info:eu-repo/semantics/altIdentifier/url/http://www.ncbi.nlm.nih.gov/pubmed/23747929info:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/doi/10.1016/j.freeradbiomed.2013.05.044info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:44:43Zoai:ri.conicet.gov.ar:11336/4817instacron: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 09:44:43.514CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Tryptophan Oxidation Photosensitizided by Pterin
title Tryptophan Oxidation Photosensitizided by Pterin
spellingShingle Tryptophan Oxidation Photosensitizided by Pterin
Thomas, Andrés Héctor
Photosensitization
Tryptophan
Pterin
title_short Tryptophan Oxidation Photosensitizided by Pterin
title_full Tryptophan Oxidation Photosensitizided by Pterin
title_fullStr Tryptophan Oxidation Photosensitizided by Pterin
title_full_unstemmed Tryptophan Oxidation Photosensitizided by Pterin
title_sort Tryptophan Oxidation Photosensitizided by Pterin
dc.creator.none.fl_str_mv Thomas, Andrés Héctor
Serrano, Mariana Paula
Rahal, Virginie
Vicendo, Patricia
Claparols, Catherine
Oliveros, Esther
Lorente, Carolina
author Thomas, Andrés Héctor
author_facet Thomas, Andrés Héctor
Serrano, Mariana Paula
Rahal, Virginie
Vicendo, Patricia
Claparols, Catherine
Oliveros, Esther
Lorente, Carolina
author_role author
author2 Serrano, Mariana Paula
Rahal, Virginie
Vicendo, Patricia
Claparols, Catherine
Oliveros, Esther
Lorente, Carolina
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Photosensitization
Tryptophan
Pterin
topic Photosensitization
Tryptophan
Pterin
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Pterins are normal components of cells and they have been previously identified as good photosensitizers under UV-A irradiation, inducing DNA damage and oxidation of nucleotides. In this work, we have investigated the ability of pterin (Ptr), the parent compound of oxidized pterins, to photosensitize the oxidation of another class of biomolecules, aminoacids, using tryptophan (Trp) as a model compound.  Irradiation of Ptr in the UV-A spectral range (350 nm) in aerated aqueous solutions containing Trp led to the consumption of the latter, whereas the Ptr concentration remained unchanged. Concomitantly, hydrogen peroxide (H2O2) was produced. Although Ptr is a singlet oxygen (1O2) sensitizer, the degradation of Trp was inhibited in O2-saturated solutions, indicating that a 1O2-mediated process (Type II oxidation) was not an important pathway leading to Trp oxidation. By combining different analytical techniques, we could establish that a Type I photooxidation was the prevailing mechanism, initiated by an electron transfer from the Trp molecule to the Ptr triplet excited state yielding the corresponding radical ions (Trp.+/Trp(-H). and Ptr.-). The Trp reaction products that could be identified by UPLC-mass spectrometry are in agreement with this conclusion.
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: Serrano, Mariana Paula. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Rahal, Virginie. Universite Paul Sabatier; Francia
Fil: Vicendo, Patricia. Universite Paul Sabatier; Francia
Fil: Claparols, Catherine. Universite Paul Sabatier; Francia
Fil: Oliveros, Esther. Universite Paul Sabatier; Francia
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 are normal components of cells and they have been previously identified as good photosensitizers under UV-A irradiation, inducing DNA damage and oxidation of nucleotides. In this work, we have investigated the ability of pterin (Ptr), the parent compound of oxidized pterins, to photosensitize the oxidation of another class of biomolecules, aminoacids, using tryptophan (Trp) as a model compound.  Irradiation of Ptr in the UV-A spectral range (350 nm) in aerated aqueous solutions containing Trp led to the consumption of the latter, whereas the Ptr concentration remained unchanged. Concomitantly, hydrogen peroxide (H2O2) was produced. Although Ptr is a singlet oxygen (1O2) sensitizer, the degradation of Trp was inhibited in O2-saturated solutions, indicating that a 1O2-mediated process (Type II oxidation) was not an important pathway leading to Trp oxidation. By combining different analytical techniques, we could establish that a Type I photooxidation was the prevailing mechanism, initiated by an electron transfer from the Trp molecule to the Ptr triplet excited state yielding the corresponding radical ions (Trp.+/Trp(-H). and Ptr.-). The Trp reaction products that could be identified by UPLC-mass spectrometry are in agreement with this conclusion.
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/11336/4817
Thomas, Andrés Héctor; Serrano, Mariana Paula; Rahal, Virginie; Vicendo, Patricia; Claparols, Catherine; et al.; Tryptophan Oxidation Photosensitizided by Pterin; Elsevier; Free Radical Biology and Medicine; 63; 5-2013; 467–475
0891-5849
url http://hdl.handle.net/11336/4817
identifier_str_mv Thomas, Andrés Héctor; Serrano, Mariana Paula; Rahal, Virginie; Vicendo, Patricia; Claparols, Catherine; et al.; Tryptophan Oxidation Photosensitizided by Pterin; Elsevier; Free Radical Biology and Medicine; 63; 5-2013; 467–475
0891-5849
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/pmid/PMID: 23747929
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0891584913002724
info:eu-repo/semantics/altIdentifier/url/http://www.ncbi.nlm.nih.gov/pubmed/23747929
info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.freeradbiomed.2013.05.044
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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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