Type I Photosensitization of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) by Biopterin and its Photoproduct Formylpterin

Autores
Serrano, Mariana Paula; Borsarelli, Claudio Darío; Thomas, Andrés Héctor
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Biopterin (Bip) and its photoproducts 6-formylpterin (Fop) and 6-carboxypterin (Cap) accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder where the protection against UV radiation fails because of the lack of melanin. These compounds absorb in the UV-A inducing a potential photosensitizing action that can cause damage to DNA and other biomolecules. In this work, we have investigated the capability of these pterin derivatives (Pt) to act as photosensitizers under UV-A irradiation for the degradation of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) in aqueous solutions, as model DNA target. Steady-state and time-resolved experiments were performed and the effect of pH was evaluated. The results showed that photosensitized degradation of 5′-dAMP was only observed under acidic conditions, and a mechanistic analysis revealed the participation of the triplet excited state of the pterin derivatives (3Pt*) by electron transfer yielding the corresponding pair of radical ions (Pt•− and 5′-dAMP•+), with successive photosensitizer recovery by electron transfer from Pt•− to O2. Finally, 5′-dAMP•+ participates in subsequent reactions to yield degradation products.
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: Borsarelli, Claudio Darío. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro de Investigaciones y Transferencia de Santiago del Estero; Argentina
Fil: Thomas, Andrés Héctor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Materia
Pterins
Photosensitization
Damp
Photodegradation
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:11336/5279
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Type I Photosensitization of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) by Biopterin and its Photoproduct FormylpterinSerrano, Mariana PaulaBorsarelli, Claudio DaríoThomas, Andrés HéctorPterinsPhotosensitizationDampPhotodegradationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Biopterin (Bip) and its photoproducts 6-formylpterin (Fop) and 6-carboxypterin (Cap) accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder where the protection against UV radiation fails because of the lack of melanin. These compounds absorb in the UV-A inducing a potential photosensitizing action that can cause damage to DNA and other biomolecules. In this work, we have investigated the capability of these pterin derivatives (Pt) to act as photosensitizers under UV-A irradiation for the degradation of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) in aqueous solutions, as model DNA target. Steady-state and time-resolved experiments were performed and the effect of pH was evaluated. The results showed that photosensitized degradation of 5′-dAMP was only observed under acidic conditions, and a mechanistic analysis revealed the participation of the triplet excited state of the pterin derivatives (3Pt*) by electron transfer yielding the corresponding pair of radical ions (Pt•− and 5′-dAMP•+), with successive photosensitizer recovery by electron transfer from Pt•− to O2. Finally, 5′-dAMP•+ participates in subsequent reactions to yield degradation products.Fil: Serrano, Mariana Paula. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaFil: Borsarelli, Claudio Darío. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro de Investigaciones y Transferencia de Santiago del Estero; ArgentinaFil: Thomas, Andrés Héctor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaWiley2013-11info: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/11336/5279Serrano, Mariana Paula; Borsarelli, Claudio Darío; Thomas, Andrés Héctor; Type I Photosensitization of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) by Biopterin and its Photoproduct Formylpterin; Wiley; Photochemistry and Photobiology; 89; 6; 11-2013; 1456-14620031-8655enginfo:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1111/php.12134/abstractinfo:eu-repo/semantics/altIdentifier/doi/10.1111/php.12134info:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:59:18Zoai:ri.conicet.gov.ar:11336/5279instacron: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 09:59:19.149CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Type I Photosensitization of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) by Biopterin and its Photoproduct Formylpterin
title Type I Photosensitization of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) by Biopterin and its Photoproduct Formylpterin
spellingShingle Type I Photosensitization of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) by Biopterin and its Photoproduct Formylpterin
Serrano, Mariana Paula
Pterins
Photosensitization
Damp
Photodegradation
title_short Type I Photosensitization of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) by Biopterin and its Photoproduct Formylpterin
title_full Type I Photosensitization of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) by Biopterin and its Photoproduct Formylpterin
title_fullStr Type I Photosensitization of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) by Biopterin and its Photoproduct Formylpterin
title_full_unstemmed Type I Photosensitization of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) by Biopterin and its Photoproduct Formylpterin
title_sort Type I Photosensitization of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) by Biopterin and its Photoproduct Formylpterin
dc.creator.none.fl_str_mv Serrano, Mariana Paula
Borsarelli, Claudio Darío
Thomas, Andrés Héctor
author Serrano, Mariana Paula
author_facet Serrano, Mariana Paula
Borsarelli, Claudio Darío
Thomas, Andrés Héctor
author_role author
author2 Borsarelli, Claudio Darío
Thomas, Andrés Héctor
author2_role author
author
dc.subject.none.fl_str_mv Pterins
Photosensitization
Damp
Photodegradation
topic Pterins
Photosensitization
Damp
Photodegradation
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Biopterin (Bip) and its photoproducts 6-formylpterin (Fop) and 6-carboxypterin (Cap) accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder where the protection against UV radiation fails because of the lack of melanin. These compounds absorb in the UV-A inducing a potential photosensitizing action that can cause damage to DNA and other biomolecules. In this work, we have investigated the capability of these pterin derivatives (Pt) to act as photosensitizers under UV-A irradiation for the degradation of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) in aqueous solutions, as model DNA target. Steady-state and time-resolved experiments were performed and the effect of pH was evaluated. The results showed that photosensitized degradation of 5′-dAMP was only observed under acidic conditions, and a mechanistic analysis revealed the participation of the triplet excited state of the pterin derivatives (3Pt*) by electron transfer yielding the corresponding pair of radical ions (Pt•− and 5′-dAMP•+), with successive photosensitizer recovery by electron transfer from Pt•− to O2. Finally, 5′-dAMP•+ participates in subsequent reactions to yield degradation products.
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: Borsarelli, Claudio Darío. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro de Investigaciones y Transferencia de Santiago del Estero; Argentina
Fil: Thomas, Andrés Héctor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
description Biopterin (Bip) and its photoproducts 6-formylpterin (Fop) and 6-carboxypterin (Cap) accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder where the protection against UV radiation fails because of the lack of melanin. These compounds absorb in the UV-A inducing a potential photosensitizing action that can cause damage to DNA and other biomolecules. In this work, we have investigated the capability of these pterin derivatives (Pt) to act as photosensitizers under UV-A irradiation for the degradation of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) in aqueous solutions, as model DNA target. Steady-state and time-resolved experiments were performed and the effect of pH was evaluated. The results showed that photosensitized degradation of 5′-dAMP was only observed under acidic conditions, and a mechanistic analysis revealed the participation of the triplet excited state of the pterin derivatives (3Pt*) by electron transfer yielding the corresponding pair of radical ions (Pt•− and 5′-dAMP•+), with successive photosensitizer recovery by electron transfer from Pt•− to O2. Finally, 5′-dAMP•+ participates in subsequent reactions to yield degradation products.
publishDate 2013
dc.date.none.fl_str_mv 2013-11
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/11336/5279
Serrano, Mariana Paula; Borsarelli, Claudio Darío; Thomas, Andrés Héctor; Type I Photosensitization of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) by Biopterin and its Photoproduct Formylpterin; Wiley; Photochemistry and Photobiology; 89; 6; 11-2013; 1456-1462
0031-8655
url http://hdl.handle.net/11336/5279
identifier_str_mv Serrano, Mariana Paula; Borsarelli, Claudio Darío; Thomas, Andrés Héctor; Type I Photosensitization of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) by Biopterin and its Photoproduct Formylpterin; Wiley; Photochemistry and Photobiology; 89; 6; 11-2013; 1456-1462
0031-8655
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1111/php.12134/abstract
info:eu-repo/semantics/altIdentifier/doi/10.1111/php.12134
info:eu-repo/semantics/altIdentifier/doi/
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
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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