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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/186832
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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 Técnicas2025-09-03T09:56:21Zoai: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:34982025-09-03 09:56:21.621CONICET 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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1842269399877156864 |
score |
13.13397 |