On the generation and quenching of reactive-oxygen-species by aqueous vitamin B2 and serotonin under visible-light irradiation

Autores
Haggi, Ernesto Sergio; Blasich, Néstor Fabian; Gutierrez, Lihuel Emiliano; Vazquez, Gabriela; Criado, Susana Noemi; Miskoski, Sandra; Ferrari, Gabriela Verónica; Montaña, Maria Paulina; Garcia, Norman Andino
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
It is well known that endogenous daylight-absorbing compounds produce the sensitized photodegradation of biologically relevant substrates. In this context the photostability of a mixture of the indole neurotransmitter serotonin (Sero) and vitamin B2 (riboflavin, Rf) upon visible-light irradiation and the possible role of Sero and related compounds as generators or deactivators of reactive oxygen species (ROS) was investigated through a kinetic and mechanistic study. The work was done at pH 7 and under experimental conditions in which only the vitamin absorbs photoirradiation. Tryptamine (Trpa) and 5-hydroxyindole(OHIn) were included in the study as model compounds for the neurotransmitter. The visible light irradiation of aqueous Rf in the individual presence of Sero, Trpa and 5-OHIn, under aerobic conditions, induce degradative processes on the indole derivatives (In-der). At least two different mechanisms operate. Our analysis shows that the main reaction pathway is an electron-transfer-mediated quenching of triplet excited Rf (3Rf) by the In-der. It produces the species Rf/RfH and the In-der radical cation that could react to form phenoxy and a-amino radicals. In a further reaction step the species O2 and OH could be produced.In parallel, energy transfer from 3Rf to dissolved oxygen would generate O2(1Dg). Within the frame of the proposed mechanism, results suggest that Rf-sensitized degradation of Sero occurs via the mentioned ROS and non-oxygenated radical-mediated processes. The indole compound quenches O2(1Dg) in a dominant physical fashion. This fact constitutes a desirable property in antioxidants, provided that the quenching process practically does not eliminate the scavenger. Sero exerts a photoprotective effect towards tryptophan through the combined quenching ofO2(1Dg) and 3Rf, the latter excited species responsible for the generation of ROS. The amino acid can be taken as a target model of oxidizable biological substrates, particularly proteins.
Fil: Haggi, Ernesto Sergio. Universidad Nacional de la Patagonia Austral; Argentina
Fil: Blasich, Néstor Fabian. Universidad Nacional de la Patagonia Austral; Argentina
Fil: Gutierrez, Lihuel Emiliano. Universidad Nacional de la Patagonia Austral; Argentina
Fil: Vazquez, Gabriela. Universidad Nacional de la Patagonia Austral; Argentina
Fil: Criado, Susana Noemi. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
Fil: Miskoski, Sandra. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
Fil: Ferrari, Gabriela Verónica. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Química de San Luis. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Química de San Luis; Argentina
Fil: Montaña, Maria Paulina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Química de San Luis. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Química de San Luis; Argentina
Fil: Garcia, Norman Andino. Universidad Nacional de Rio Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química y Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
SEROTONIN
PHOTOOXIDATION
RIBOFLAVIN
REACTIVE OXYGEN SPECIES
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:11336/110959
Acceder
id CONICETDig_3d5018aef43292b724391522eb8f5578
oai_identifier_str oai:ri.conicet.gov.ar:11336/110959
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling On the generation and quenching of reactive-oxygen-species by aqueous vitamin B2 and serotonin under visible-light irradiationHaggi, Ernesto SergioBlasich, Néstor FabianGutierrez, Lihuel EmilianoVazquez, GabrielaCriado, Susana NoemiMiskoski, SandraFerrari, Gabriela VerónicaMontaña, Maria PaulinaGarcia, Norman AndinoSEROTONINPHOTOOXIDATIONRIBOFLAVINREACTIVE OXYGEN SPECIEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1It is well known that endogenous daylight-absorbing compounds produce the sensitized photodegradation of biologically relevant substrates. In this context the photostability of a mixture of the indole neurotransmitter serotonin (Sero) and vitamin B2 (riboflavin, Rf) upon visible-light irradiation and the possible role of Sero and related compounds as generators or deactivators of reactive oxygen species (ROS) was investigated through a kinetic and mechanistic study. The work was done at pH 7 and under experimental conditions in which only the vitamin absorbs photoirradiation. Tryptamine (Trpa) and 5-hydroxyindole(OHIn) were included in the study as model compounds for the neurotransmitter. The visible light irradiation of aqueous Rf in the individual presence of Sero, Trpa and 5-OHIn, under aerobic conditions, induce degradative processes on the indole derivatives (In-der). At least two different mechanisms operate. Our analysis shows that the main reaction pathway is an electron-transfer-mediated quenching of triplet excited Rf (3Rf) by the In-der. It produces the species Rf/RfH and the In-der radical cation that could react to form phenoxy and a-amino radicals. In a further reaction step the species O2 and OH could be produced.In parallel, energy transfer from 3Rf to dissolved oxygen would generate O2(1Dg). Within the frame of the proposed mechanism, results suggest that Rf-sensitized degradation of Sero occurs via the mentioned ROS and non-oxygenated radical-mediated processes. The indole compound quenches O2(1Dg) in a dominant physical fashion. This fact constitutes a desirable property in antioxidants, provided that the quenching process practically does not eliminate the scavenger. Sero exerts a photoprotective effect towards tryptophan through the combined quenching ofO2(1Dg) and 3Rf, the latter excited species responsible for the generation of ROS. The amino acid can be taken as a target model of oxidizable biological substrates, particularly proteins.Fil: Haggi, Ernesto Sergio. Universidad Nacional de la Patagonia Austral; ArgentinaFil: Blasich, Néstor Fabian. Universidad Nacional de la Patagonia Austral; ArgentinaFil: Gutierrez, Lihuel Emiliano. Universidad Nacional de la Patagonia Austral; ArgentinaFil: Vazquez, Gabriela. Universidad Nacional de la Patagonia Austral; ArgentinaFil: Criado, Susana Noemi. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; ArgentinaFil: Miskoski, Sandra. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; ArgentinaFil: Ferrari, Gabriela Verónica. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Química de San Luis. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Química de San Luis; ArgentinaFil: Montaña, Maria Paulina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Química de San Luis. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Química de San Luis; ArgentinaFil: Garcia, Norman Andino. Universidad Nacional de Rio Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química y Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaElsevier Science Sa2012-04info: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/11336/110959Haggi, Ernesto Sergio; Blasich, Néstor Fabian; Gutierrez, Lihuel Emiliano; Vazquez, Gabriela; Criado, Susana Noemi; et al.; On the generation and quenching of reactive-oxygen-species by aqueous vitamin B2 and serotonin under visible-light irradiation; Elsevier Science Sa; Journal of Photochemistry and Photobiology B: Biology; 113; 4-2012; 22-281011-1344CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotobiol.2012.04.010info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S101113441200084Xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:46:14Zoai:ri.conicet.gov.ar:11336/110959instacron: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 09:46:14.884CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv On the generation and quenching of reactive-oxygen-species by aqueous vitamin B2 and serotonin under visible-light irradiation
title On the generation and quenching of reactive-oxygen-species by aqueous vitamin B2 and serotonin under visible-light irradiation
spellingShingle On the generation and quenching of reactive-oxygen-species by aqueous vitamin B2 and serotonin under visible-light irradiation
Haggi, Ernesto Sergio
SEROTONIN
PHOTOOXIDATION
RIBOFLAVIN
REACTIVE OXYGEN SPECIES
title_short On the generation and quenching of reactive-oxygen-species by aqueous vitamin B2 and serotonin under visible-light irradiation
title_full On the generation and quenching of reactive-oxygen-species by aqueous vitamin B2 and serotonin under visible-light irradiation
title_fullStr On the generation and quenching of reactive-oxygen-species by aqueous vitamin B2 and serotonin under visible-light irradiation
title_full_unstemmed On the generation and quenching of reactive-oxygen-species by aqueous vitamin B2 and serotonin under visible-light irradiation
title_sort On the generation and quenching of reactive-oxygen-species by aqueous vitamin B2 and serotonin under visible-light irradiation
dc.creator.none.fl_str_mv Haggi, Ernesto Sergio
Blasich, Néstor Fabian
Gutierrez, Lihuel Emiliano
Vazquez, Gabriela
Criado, Susana Noemi
Miskoski, Sandra
Ferrari, Gabriela Verónica
Montaña, Maria Paulina
Garcia, Norman Andino
author Haggi, Ernesto Sergio
author_facet Haggi, Ernesto Sergio
Blasich, Néstor Fabian
Gutierrez, Lihuel Emiliano
Vazquez, Gabriela
Criado, Susana Noemi
Miskoski, Sandra
Ferrari, Gabriela Verónica
Montaña, Maria Paulina
Garcia, Norman Andino
author_role author
author2 Blasich, Néstor Fabian
Gutierrez, Lihuel Emiliano
Vazquez, Gabriela
Criado, Susana Noemi
Miskoski, Sandra
Ferrari, Gabriela Verónica
Montaña, Maria Paulina
Garcia, Norman Andino
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv SEROTONIN
PHOTOOXIDATION
RIBOFLAVIN
REACTIVE OXYGEN SPECIES
topic SEROTONIN
PHOTOOXIDATION
RIBOFLAVIN
REACTIVE OXYGEN SPECIES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv It is well known that endogenous daylight-absorbing compounds produce the sensitized photodegradation of biologically relevant substrates. In this context the photostability of a mixture of the indole neurotransmitter serotonin (Sero) and vitamin B2 (riboflavin, Rf) upon visible-light irradiation and the possible role of Sero and related compounds as generators or deactivators of reactive oxygen species (ROS) was investigated through a kinetic and mechanistic study. The work was done at pH 7 and under experimental conditions in which only the vitamin absorbs photoirradiation. Tryptamine (Trpa) and 5-hydroxyindole(OHIn) were included in the study as model compounds for the neurotransmitter. The visible light irradiation of aqueous Rf in the individual presence of Sero, Trpa and 5-OHIn, under aerobic conditions, induce degradative processes on the indole derivatives (In-der). At least two different mechanisms operate. Our analysis shows that the main reaction pathway is an electron-transfer-mediated quenching of triplet excited Rf (3Rf) by the In-der. It produces the species Rf/RfH and the In-der radical cation that could react to form phenoxy and a-amino radicals. In a further reaction step the species O2 and OH could be produced.In parallel, energy transfer from 3Rf to dissolved oxygen would generate O2(1Dg). Within the frame of the proposed mechanism, results suggest that Rf-sensitized degradation of Sero occurs via the mentioned ROS and non-oxygenated radical-mediated processes. The indole compound quenches O2(1Dg) in a dominant physical fashion. This fact constitutes a desirable property in antioxidants, provided that the quenching process practically does not eliminate the scavenger. Sero exerts a photoprotective effect towards tryptophan through the combined quenching ofO2(1Dg) and 3Rf, the latter excited species responsible for the generation of ROS. The amino acid can be taken as a target model of oxidizable biological substrates, particularly proteins.
Fil: Haggi, Ernesto Sergio. Universidad Nacional de la Patagonia Austral; Argentina
Fil: Blasich, Néstor Fabian. Universidad Nacional de la Patagonia Austral; Argentina
Fil: Gutierrez, Lihuel Emiliano. Universidad Nacional de la Patagonia Austral; Argentina
Fil: Vazquez, Gabriela. Universidad Nacional de la Patagonia Austral; Argentina
Fil: Criado, Susana Noemi. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
Fil: Miskoski, Sandra. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
Fil: Ferrari, Gabriela Verónica. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Química de San Luis. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Química de San Luis; Argentina
Fil: Montaña, Maria Paulina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Química de San Luis. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Química de San Luis; Argentina
Fil: Garcia, Norman Andino. Universidad Nacional de Rio Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química y Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description It is well known that endogenous daylight-absorbing compounds produce the sensitized photodegradation of biologically relevant substrates. In this context the photostability of a mixture of the indole neurotransmitter serotonin (Sero) and vitamin B2 (riboflavin, Rf) upon visible-light irradiation and the possible role of Sero and related compounds as generators or deactivators of reactive oxygen species (ROS) was investigated through a kinetic and mechanistic study. The work was done at pH 7 and under experimental conditions in which only the vitamin absorbs photoirradiation. Tryptamine (Trpa) and 5-hydroxyindole(OHIn) were included in the study as model compounds for the neurotransmitter. The visible light irradiation of aqueous Rf in the individual presence of Sero, Trpa and 5-OHIn, under aerobic conditions, induce degradative processes on the indole derivatives (In-der). At least two different mechanisms operate. Our analysis shows that the main reaction pathway is an electron-transfer-mediated quenching of triplet excited Rf (3Rf) by the In-der. It produces the species Rf/RfH and the In-der radical cation that could react to form phenoxy and a-amino radicals. In a further reaction step the species O2 and OH could be produced.In parallel, energy transfer from 3Rf to dissolved oxygen would generate O2(1Dg). Within the frame of the proposed mechanism, results suggest that Rf-sensitized degradation of Sero occurs via the mentioned ROS and non-oxygenated radical-mediated processes. The indole compound quenches O2(1Dg) in a dominant physical fashion. This fact constitutes a desirable property in antioxidants, provided that the quenching process practically does not eliminate the scavenger. Sero exerts a photoprotective effect towards tryptophan through the combined quenching ofO2(1Dg) and 3Rf, the latter excited species responsible for the generation of ROS. The amino acid can be taken as a target model of oxidizable biological substrates, particularly proteins.
publishDate 2012
dc.date.none.fl_str_mv 2012-04
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/11336/110959
Haggi, Ernesto Sergio; Blasich, Néstor Fabian; Gutierrez, Lihuel Emiliano; Vazquez, Gabriela; Criado, Susana Noemi; et al.; On the generation and quenching of reactive-oxygen-species by aqueous vitamin B2 and serotonin under visible-light irradiation; Elsevier Science Sa; Journal of Photochemistry and Photobiology B: Biology; 113; 4-2012; 22-28
1011-1344
CONICET Digital
CONICET
url http://hdl.handle.net/11336/110959
identifier_str_mv Haggi, Ernesto Sergio; Blasich, Néstor Fabian; Gutierrez, Lihuel Emiliano; Vazquez, Gabriela; Criado, Susana Noemi; et al.; On the generation and quenching of reactive-oxygen-species by aqueous vitamin B2 and serotonin under visible-light irradiation; Elsevier Science Sa; Journal of Photochemistry and Photobiology B: Biology; 113; 4-2012; 22-28
1011-1344
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotobiol.2012.04.010
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S101113441200084X
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/
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application/pdf
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dc.publisher.none.fl_str_mv Elsevier Science Sa
publisher.none.fl_str_mv Elsevier Science Sa
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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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