Oxidation of 2′-Deoxyadenosine 5′-Monophosphate Photoinduced by Lumazine

Autores
Denofrio, Maria Paula; Thomas, Andrés Héctor; Lorente, Carolina
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
UV radiation induces damages to the DNA molecule and its components through photosensitized reactions. Among these processes, photosensitized oxidations may occur through electron transfer or hydrogen abstraction (type I mechanism) and/or the production of singlet molecular oxygen (1 O2) (type II mechanism). Lumazines are an important family of heterocyclic compounds present in biological systems as biosynthetic precursors and/or products of metabolic degradation. To evaluate the capability of lumazines to act as photosensitizers through type I mechanism, we have investigated the oxidation of 2′-deoxyadenosine 5′-monophosphate (dAMP) photosensitized by the specific compound called lumazine (pteridine-2,4(1,3H)-dione; Lum) in aqueous solutions under UV irradiation. The photochemical reactions were followed by UV/vis spectrophotometry, HPLC, electrochemical measurement of dissolved O2, and an enzymatic method for H2O2 determination. The effect of pH was evaluated and the participation of oxygen was investigated. In aerated solutions, oxidation of dAMP photoinduced by the acid form of Lum (pH 5.5) takes place through a type I mechanism, in which the excitation of Lum is followed by an electron transfer from dAMP molecule to the Lum triplet excited state. During the process, O2 is consumed and H2O2 is generated, whereas the photosensitizer is not consumed. In contrast, no evidence of a photochemical reaction induced by the basic form of Lum (pH 10.5) was observed.
Fil: Denofrio, Maria Paula. 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: 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
PHOTOSENSITIZATION
LUMAZINE
NUCLEOTIDE
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:11336/241337
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Oxidation of 2′-Deoxyadenosine 5′-Monophosphate Photoinduced by LumazineDenofrio, Maria PaulaThomas, Andrés HéctorLorente, CarolinaPHOTOSENSITIZATIONLUMAZINENUCLEOTIDEhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1UV radiation induces damages to the DNA molecule and its components through photosensitized reactions. Among these processes, photosensitized oxidations may occur through electron transfer or hydrogen abstraction (type I mechanism) and/or the production of singlet molecular oxygen (1 O2) (type II mechanism). Lumazines are an important family of heterocyclic compounds present in biological systems as biosynthetic precursors and/or products of metabolic degradation. To evaluate the capability of lumazines to act as photosensitizers through type I mechanism, we have investigated the oxidation of 2′-deoxyadenosine 5′-monophosphate (dAMP) photosensitized by the specific compound called lumazine (pteridine-2,4(1,3H)-dione; Lum) in aqueous solutions under UV irradiation. The photochemical reactions were followed by UV/vis spectrophotometry, HPLC, electrochemical measurement of dissolved O2, and an enzymatic method for H2O2 determination. The effect of pH was evaluated and the participation of oxygen was investigated. In aerated solutions, oxidation of dAMP photoinduced by the acid form of Lum (pH 5.5) takes place through a type I mechanism, in which the excitation of Lum is followed by an electron transfer from dAMP molecule to the Lum triplet excited state. During the process, O2 is consumed and H2O2 is generated, whereas the photosensitizer is not consumed. In contrast, no evidence of a photochemical reaction induced by the basic form of Lum (pH 10.5) was observed.Fil: Denofrio, Maria Paula. 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: 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; ArgentinaAmerican Chemical Society2010-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/241337Denofrio, Maria Paula; Thomas, Andrés Héctor; Lorente, Carolina; Oxidation of 2′-Deoxyadenosine 5′-Monophosphate Photoinduced by Lumazine; American Chemical Society; Journal of Physical Chemistry A; 114; 41; 9-2010; 10944-109501089-5639CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jp1061336info:eu-repo/semantics/altIdentifier/doi/10.1021/jp1061336info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:55:16Zoai:ri.conicet.gov.ar:11336/241337instacron: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 09:55:16.619CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Oxidation of 2′-Deoxyadenosine 5′-Monophosphate Photoinduced by Lumazine
title Oxidation of 2′-Deoxyadenosine 5′-Monophosphate Photoinduced by Lumazine
spellingShingle Oxidation of 2′-Deoxyadenosine 5′-Monophosphate Photoinduced by Lumazine
Denofrio, Maria Paula
PHOTOSENSITIZATION
LUMAZINE
NUCLEOTIDE
title_short Oxidation of 2′-Deoxyadenosine 5′-Monophosphate Photoinduced by Lumazine
title_full Oxidation of 2′-Deoxyadenosine 5′-Monophosphate Photoinduced by Lumazine
title_fullStr Oxidation of 2′-Deoxyadenosine 5′-Monophosphate Photoinduced by Lumazine
title_full_unstemmed Oxidation of 2′-Deoxyadenosine 5′-Monophosphate Photoinduced by Lumazine
title_sort Oxidation of 2′-Deoxyadenosine 5′-Monophosphate Photoinduced by Lumazine
dc.creator.none.fl_str_mv Denofrio, Maria Paula
Thomas, Andrés Héctor
Lorente, Carolina
author Denofrio, Maria Paula
author_facet Denofrio, Maria Paula
Thomas, Andrés Héctor
Lorente, Carolina
author_role author
author2 Thomas, Andrés Héctor
Lorente, Carolina
author2_role author
author
dc.subject.none.fl_str_mv PHOTOSENSITIZATION
LUMAZINE
NUCLEOTIDE
topic PHOTOSENSITIZATION
LUMAZINE
NUCLEOTIDE
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv UV radiation induces damages to the DNA molecule and its components through photosensitized reactions. Among these processes, photosensitized oxidations may occur through electron transfer or hydrogen abstraction (type I mechanism) and/or the production of singlet molecular oxygen (1 O2) (type II mechanism). Lumazines are an important family of heterocyclic compounds present in biological systems as biosynthetic precursors and/or products of metabolic degradation. To evaluate the capability of lumazines to act as photosensitizers through type I mechanism, we have investigated the oxidation of 2′-deoxyadenosine 5′-monophosphate (dAMP) photosensitized by the specific compound called lumazine (pteridine-2,4(1,3H)-dione; Lum) in aqueous solutions under UV irradiation. The photochemical reactions were followed by UV/vis spectrophotometry, HPLC, electrochemical measurement of dissolved O2, and an enzymatic method for H2O2 determination. The effect of pH was evaluated and the participation of oxygen was investigated. In aerated solutions, oxidation of dAMP photoinduced by the acid form of Lum (pH 5.5) takes place through a type I mechanism, in which the excitation of Lum is followed by an electron transfer from dAMP molecule to the Lum triplet excited state. During the process, O2 is consumed and H2O2 is generated, whereas the photosensitizer is not consumed. In contrast, no evidence of a photochemical reaction induced by the basic form of Lum (pH 10.5) was observed.
Fil: Denofrio, Maria Paula. 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: 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 UV radiation induces damages to the DNA molecule and its components through photosensitized reactions. Among these processes, photosensitized oxidations may occur through electron transfer or hydrogen abstraction (type I mechanism) and/or the production of singlet molecular oxygen (1 O2) (type II mechanism). Lumazines are an important family of heterocyclic compounds present in biological systems as biosynthetic precursors and/or products of metabolic degradation. To evaluate the capability of lumazines to act as photosensitizers through type I mechanism, we have investigated the oxidation of 2′-deoxyadenosine 5′-monophosphate (dAMP) photosensitized by the specific compound called lumazine (pteridine-2,4(1,3H)-dione; Lum) in aqueous solutions under UV irradiation. The photochemical reactions were followed by UV/vis spectrophotometry, HPLC, electrochemical measurement of dissolved O2, and an enzymatic method for H2O2 determination. The effect of pH was evaluated and the participation of oxygen was investigated. In aerated solutions, oxidation of dAMP photoinduced by the acid form of Lum (pH 5.5) takes place through a type I mechanism, in which the excitation of Lum is followed by an electron transfer from dAMP molecule to the Lum triplet excited state. During the process, O2 is consumed and H2O2 is generated, whereas the photosensitizer is not consumed. In contrast, no evidence of a photochemical reaction induced by the basic form of Lum (pH 10.5) was observed.
publishDate 2010
dc.date.none.fl_str_mv 2010-09
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/11336/241337
Denofrio, Maria Paula; Thomas, Andrés Héctor; Lorente, Carolina; Oxidation of 2′-Deoxyadenosine 5′-Monophosphate Photoinduced by Lumazine; American Chemical Society; Journal of Physical Chemistry A; 114; 41; 9-2010; 10944-10950
1089-5639
CONICET Digital
CONICET
url http://hdl.handle.net/11336/241337
identifier_str_mv Denofrio, Maria Paula; Thomas, Andrés Héctor; Lorente, Carolina; Oxidation of 2′-Deoxyadenosine 5′-Monophosphate Photoinduced by Lumazine; American Chemical Society; Journal of Physical Chemistry A; 114; 41; 9-2010; 10944-10950
1089-5639
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jp1061336
info:eu-repo/semantics/altIdentifier/doi/10.1021/jp1061336
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
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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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