A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species

Autores
Criado, Susana Noemi; Garcia, Norman Andino
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Kinetic and mechanistic aspects of the vitamin B2 (riboflavin [Rf])-sensitized photo-oxidation of the imidazoline derivates (IDs) naphazoline (NPZ) and tetrahydrozoline (THZ) were investigated in aqueous solution. The process appears as important on biomedical grounds, considering that the vitamin is endogenously present in humans, and IDs are active components of ocular medicaments of topical application. Under aerobic visible light irradiation, a complex picture of competitive interactions between sensitizer, substrates and dissolved oxygen takes place: the singlet and triplet (3Rf*) excited states of Rf are quenched by the IDs: with IDs concentrations ca. 5.0 mm and 0.02 mm Rf, 3Rf* is quenched by IDs, in a competitive fashion with dissolved ground state oxygen. Additionally, the reactive oxygen species: O2(1Δg), O2 •-, HO• and H2O2, generated from 3Rf* and Rf•-, were detected with the employment of time-resolved methods or specific scavengers. Oxygen uptake experiments indicate that, for NPZ, only H2O2 was involved in the photo-oxidation. In the case of THZ, O2 •-, HO• and H2O2 were detected, whereas only HO• was unambiguously identified as THZ oxidative agents. Upon direct UV light irradiation NPZ and THZ generate O 2(1Δg.), with quantum yields of 0.2 (literature value, employed as a reference) and 0.08, respectively, in acetonitrile.
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: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química y Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
NAPHAZOLINE
TETRAHIDROZOLINE
REACTIVE OXYGEN SPECIES
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:11336/186832
Acceder
id CONICETDig_bdafdef58be68541601a35811a59a21a
oai_identifier_str oai:ri.conicet.gov.ar:11336/186832
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen speciesCriado, Susana NoemiGarcia, Norman AndinoNAPHAZOLINETETRAHIDROZOLINEREACTIVE OXYGEN SPECIESPHOTODEGRADATIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Kinetic and mechanistic aspects of the vitamin B2 (riboflavin [Rf])-sensitized photo-oxidation of the imidazoline derivates (IDs) naphazoline (NPZ) and tetrahydrozoline (THZ) were investigated in aqueous solution. The process appears as important on biomedical grounds, considering that the vitamin is endogenously present in humans, and IDs are active components of ocular medicaments of topical application. Under aerobic visible light irradiation, a complex picture of competitive interactions between sensitizer, substrates and dissolved oxygen takes place: the singlet and triplet (3Rf*) excited states of Rf are quenched by the IDs: with IDs concentrations ca. 5.0 mm and 0.02 mm Rf, 3Rf* is quenched by IDs, in a competitive fashion with dissolved ground state oxygen. Additionally, the reactive oxygen species: O2(1Δg), O2 •-, HO• and H2O2, generated from 3Rf* and Rf•-, were detected with the employment of time-resolved methods or specific scavengers. Oxygen uptake experiments indicate that, for NPZ, only H2O2 was involved in the photo-oxidation. In the case of THZ, O2 •-, HO• and H2O2 were detected, whereas only HO• was unambiguously identified as THZ oxidative agents. Upon direct UV light irradiation NPZ and THZ generate O 2(1Δg.), with quantum yields of 0.2 (literature value, employed as a reference) and 0.08, respectively, in acetonitrile.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; ArgentinaFil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química y Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaWiley Blackwell Publishing, Inc2010-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/186832Criado, Susana Noemi; Garcia, Norman Andino; A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species; Wiley Blackwell Publishing, Inc; Photochemistry and Photobiology; 86; 1; 1-2010; 23-300031-86551751-1097CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1111/j.1751-1097.2009.00616.xinfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1111/j.1751-1097.2009.00616.xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:00:33Zoai:ri.conicet.gov.ar:11336/186832instacron: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 10:00:33.295CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species
title A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species
spellingShingle A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species
Criado, Susana Noemi
NAPHAZOLINE
TETRAHIDROZOLINE
REACTIVE OXYGEN SPECIES
PHOTODEGRADATION
title_short A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species
title_full A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species
title_fullStr A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species
title_full_unstemmed A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species
title_sort A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species
dc.creator.none.fl_str_mv Criado, Susana Noemi
Garcia, Norman Andino
author Criado, Susana Noemi
author_facet Criado, Susana Noemi
Garcia, Norman Andino
author_role author
author2 Garcia, Norman Andino
author2_role author
dc.subject.none.fl_str_mv NAPHAZOLINE
TETRAHIDROZOLINE
REACTIVE OXYGEN SPECIES
PHOTODEGRADATION
topic NAPHAZOLINE
TETRAHIDROZOLINE
REACTIVE OXYGEN SPECIES
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 Kinetic and mechanistic aspects of the vitamin B2 (riboflavin [Rf])-sensitized photo-oxidation of the imidazoline derivates (IDs) naphazoline (NPZ) and tetrahydrozoline (THZ) were investigated in aqueous solution. The process appears as important on biomedical grounds, considering that the vitamin is endogenously present in humans, and IDs are active components of ocular medicaments of topical application. Under aerobic visible light irradiation, a complex picture of competitive interactions between sensitizer, substrates and dissolved oxygen takes place: the singlet and triplet (3Rf*) excited states of Rf are quenched by the IDs: with IDs concentrations ca. 5.0 mm and 0.02 mm Rf, 3Rf* is quenched by IDs, in a competitive fashion with dissolved ground state oxygen. Additionally, the reactive oxygen species: O2(1Δg), O2 •-, HO• and H2O2, generated from 3Rf* and Rf•-, were detected with the employment of time-resolved methods or specific scavengers. Oxygen uptake experiments indicate that, for NPZ, only H2O2 was involved in the photo-oxidation. In the case of THZ, O2 •-, HO• and H2O2 were detected, whereas only HO• was unambiguously identified as THZ oxidative agents. Upon direct UV light irradiation NPZ and THZ generate O 2(1Δg.), with quantum yields of 0.2 (literature value, employed as a reference) and 0.08, respectively, in acetonitrile.
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: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química y Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description Kinetic and mechanistic aspects of the vitamin B2 (riboflavin [Rf])-sensitized photo-oxidation of the imidazoline derivates (IDs) naphazoline (NPZ) and tetrahydrozoline (THZ) were investigated in aqueous solution. The process appears as important on biomedical grounds, considering that the vitamin is endogenously present in humans, and IDs are active components of ocular medicaments of topical application. Under aerobic visible light irradiation, a complex picture of competitive interactions between sensitizer, substrates and dissolved oxygen takes place: the singlet and triplet (3Rf*) excited states of Rf are quenched by the IDs: with IDs concentrations ca. 5.0 mm and 0.02 mm Rf, 3Rf* is quenched by IDs, in a competitive fashion with dissolved ground state oxygen. Additionally, the reactive oxygen species: O2(1Δg), O2 •-, HO• and H2O2, generated from 3Rf* and Rf•-, were detected with the employment of time-resolved methods or specific scavengers. Oxygen uptake experiments indicate that, for NPZ, only H2O2 was involved in the photo-oxidation. In the case of THZ, O2 •-, HO• and H2O2 were detected, whereas only HO• was unambiguously identified as THZ oxidative agents. Upon direct UV light irradiation NPZ and THZ generate O 2(1Δg.), with quantum yields of 0.2 (literature value, employed as a reference) and 0.08, respectively, in acetonitrile.
publishDate 2010
dc.date.none.fl_str_mv 2010-01
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/11336/186832
Criado, Susana Noemi; Garcia, Norman Andino; A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species; Wiley Blackwell Publishing, Inc; Photochemistry and Photobiology; 86; 1; 1-2010; 23-30
0031-8655
1751-1097
CONICET Digital
CONICET
url http://hdl.handle.net/11336/186832
identifier_str_mv Criado, Susana Noemi; Garcia, Norman Andino; A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species; Wiley Blackwell Publishing, Inc; Photochemistry and Photobiology; 86; 1; 1-2010; 23-30
0031-8655
1751-1097
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1111/j.1751-1097.2009.00616.x
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1111/j.1751-1097.2009.00616.x
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
dc.publisher.none.fl_str_mv Wiley Blackwell Publishing, Inc
publisher.none.fl_str_mv Wiley Blackwell Publishing, Inc
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 13.069144

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