Acetazolamide as a singlet molecular oxygen quencher

Autores
Valencia, Cristina; Tobon, Eduard; Castaño Espinal, Diana Carolina
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
According to literature the acetazolamide, which is commonly used as a diuretic, shows phototoxic properties. To contribute to the understanding of the role of this chemical as a generator of the very common toxic substance, the singlet molecular oxygen, O 2 ( 1 Δ g ), in this paper we show a kinetic study about the photosensitized oxidation of acetazolamide and its photosensitizing nature in the generation of O 2 ( 1 Δ g ). Contrary to our expectations, results show that this drug has a predominant activity as an O 2 ( 1 Δ g ) deactivator and its ability to generate the singlet oxygen is small. To find the mechanism of this activity, chemical reactivity constants measured in several solvents were adjusted to first-order kinetics. We found very moderate values around 10 5 M -1 s -1 , which compared to the total rate, the sum of the physical and chemical rate constants, of around 10 7 M -1 s -1 , supports a physical type of quench as the main acetazolamide deactivation pathway of O 2 ( 1 Δ g ). Additionally, due to a moderate solvent effect of the reaction between acetazolamide and O 2 ( 1 Δ g ) it is possible to postulate the formation of an exciplex complex with small charge separation. Finally, quantum yield values for the generation of singlet oxygen, determined through steady-state experiments, are 0.056, 0.097, and 0.015 in methanol, ethanol, and acetonitrile, respectively. Therefore, we can conclude that acetazolamide is an efficient quencher of singlet molecular oxygen (mainly of the physical type) and its phototoxic activity may involve other species different from singlet oxygen.
Fil: Valencia, Cristina. Universidad Nacional de Colombia; Colombia
Fil: Tobon, Eduard. Universidad Nacional de Colombia; Colombia
Fil: Castaño Espinal, Diana 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. Universidad Nacional de Colombia; Colombia
Materia
Acetazolamide
Quencher
Singlet Molecular Oxygen
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/82995
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/82995
network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Acetazolamide as a singlet molecular oxygen quencherValencia, CristinaTobon, EduardCastaño Espinal, Diana CarolinaAcetazolamideQuencherSinglet Molecular Oxygenhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1According to literature the acetazolamide, which is commonly used as a diuretic, shows phototoxic properties. To contribute to the understanding of the role of this chemical as a generator of the very common toxic substance, the singlet molecular oxygen, O 2 ( 1 Δ g ), in this paper we show a kinetic study about the photosensitized oxidation of acetazolamide and its photosensitizing nature in the generation of O 2 ( 1 Δ g ). Contrary to our expectations, results show that this drug has a predominant activity as an O 2 ( 1 Δ g ) deactivator and its ability to generate the singlet oxygen is small. To find the mechanism of this activity, chemical reactivity constants measured in several solvents were adjusted to first-order kinetics. We found very moderate values around 10 5 M -1 s -1 , which compared to the total rate, the sum of the physical and chemical rate constants, of around 10 7 M -1 s -1 , supports a physical type of quench as the main acetazolamide deactivation pathway of O 2 ( 1 Δ g ). Additionally, due to a moderate solvent effect of the reaction between acetazolamide and O 2 ( 1 Δ g ) it is possible to postulate the formation of an exciplex complex with small charge separation. Finally, quantum yield values for the generation of singlet oxygen, determined through steady-state experiments, are 0.056, 0.097, and 0.015 in methanol, ethanol, and acetonitrile, respectively. Therefore, we can conclude that acetazolamide is an efficient quencher of singlet molecular oxygen (mainly of the physical type) and its phototoxic activity may involve other species different from singlet oxygen.Fil: Valencia, Cristina. Universidad Nacional de Colombia; ColombiaFil: Tobon, Eduard. Universidad Nacional de Colombia; ColombiaFil: Castaño Espinal, Diana 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. Universidad Nacional de Colombia; ColombiaElsevier Science2013-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/82995Valencia, Cristina; Tobon, Eduard; Castaño Espinal, Diana Carolina; Acetazolamide as a singlet molecular oxygen quencher; Elsevier Science; Journal of Photochemistry and Photobiology A: Chemistry; 251; 8-2013; 113-1171010-6030CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1010603012005035info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2012.10.016info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:09:40Zoai:ri.conicet.gov.ar:11336/82995instacron: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 10:09:40.282CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Acetazolamide as a singlet molecular oxygen quencher
title Acetazolamide as a singlet molecular oxygen quencher
spellingShingle Acetazolamide as a singlet molecular oxygen quencher
Valencia, Cristina
Acetazolamide
Quencher
Singlet Molecular Oxygen
title_short Acetazolamide as a singlet molecular oxygen quencher
title_full Acetazolamide as a singlet molecular oxygen quencher
title_fullStr Acetazolamide as a singlet molecular oxygen quencher
title_full_unstemmed Acetazolamide as a singlet molecular oxygen quencher
title_sort Acetazolamide as a singlet molecular oxygen quencher
dc.creator.none.fl_str_mv Valencia, Cristina
Tobon, Eduard
Castaño Espinal, Diana Carolina
author Valencia, Cristina
author_facet Valencia, Cristina
Tobon, Eduard
Castaño Espinal, Diana Carolina
author_role author
author2 Tobon, Eduard
Castaño Espinal, Diana Carolina
author2_role author
author
dc.subject.none.fl_str_mv Acetazolamide
Quencher
Singlet Molecular Oxygen
topic Acetazolamide
Quencher
Singlet Molecular Oxygen
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv According to literature the acetazolamide, which is commonly used as a diuretic, shows phototoxic properties. To contribute to the understanding of the role of this chemical as a generator of the very common toxic substance, the singlet molecular oxygen, O 2 ( 1 Δ g ), in this paper we show a kinetic study about the photosensitized oxidation of acetazolamide and its photosensitizing nature in the generation of O 2 ( 1 Δ g ). Contrary to our expectations, results show that this drug has a predominant activity as an O 2 ( 1 Δ g ) deactivator and its ability to generate the singlet oxygen is small. To find the mechanism of this activity, chemical reactivity constants measured in several solvents were adjusted to first-order kinetics. We found very moderate values around 10 5 M -1 s -1 , which compared to the total rate, the sum of the physical and chemical rate constants, of around 10 7 M -1 s -1 , supports a physical type of quench as the main acetazolamide deactivation pathway of O 2 ( 1 Δ g ). Additionally, due to a moderate solvent effect of the reaction between acetazolamide and O 2 ( 1 Δ g ) it is possible to postulate the formation of an exciplex complex with small charge separation. Finally, quantum yield values for the generation of singlet oxygen, determined through steady-state experiments, are 0.056, 0.097, and 0.015 in methanol, ethanol, and acetonitrile, respectively. Therefore, we can conclude that acetazolamide is an efficient quencher of singlet molecular oxygen (mainly of the physical type) and its phototoxic activity may involve other species different from singlet oxygen.
Fil: Valencia, Cristina. Universidad Nacional de Colombia; Colombia
Fil: Tobon, Eduard. Universidad Nacional de Colombia; Colombia
Fil: Castaño Espinal, Diana 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. Universidad Nacional de Colombia; Colombia
description According to literature the acetazolamide, which is commonly used as a diuretic, shows phototoxic properties. To contribute to the understanding of the role of this chemical as a generator of the very common toxic substance, the singlet molecular oxygen, O 2 ( 1 Δ g ), in this paper we show a kinetic study about the photosensitized oxidation of acetazolamide and its photosensitizing nature in the generation of O 2 ( 1 Δ g ). Contrary to our expectations, results show that this drug has a predominant activity as an O 2 ( 1 Δ g ) deactivator and its ability to generate the singlet oxygen is small. To find the mechanism of this activity, chemical reactivity constants measured in several solvents were adjusted to first-order kinetics. We found very moderate values around 10 5 M -1 s -1 , which compared to the total rate, the sum of the physical and chemical rate constants, of around 10 7 M -1 s -1 , supports a physical type of quench as the main acetazolamide deactivation pathway of O 2 ( 1 Δ g ). Additionally, due to a moderate solvent effect of the reaction between acetazolamide and O 2 ( 1 Δ g ) it is possible to postulate the formation of an exciplex complex with small charge separation. Finally, quantum yield values for the generation of singlet oxygen, determined through steady-state experiments, are 0.056, 0.097, and 0.015 in methanol, ethanol, and acetonitrile, respectively. Therefore, we can conclude that acetazolamide is an efficient quencher of singlet molecular oxygen (mainly of the physical type) and its phototoxic activity may involve other species different from singlet oxygen.
publishDate 2013
dc.date.none.fl_str_mv 2013-08
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/11336/82995
Valencia, Cristina; Tobon, Eduard; Castaño Espinal, Diana Carolina; Acetazolamide as a singlet molecular oxygen quencher; Elsevier Science; Journal of Photochemistry and Photobiology A: Chemistry; 251; 8-2013; 113-117
1010-6030
CONICET Digital
CONICET
url http://hdl.handle.net/11336/82995
identifier_str_mv Valencia, Cristina; Tobon, Eduard; Castaño Espinal, Diana Carolina; Acetazolamide as a singlet molecular oxygen quencher; Elsevier Science; Journal of Photochemistry and Photobiology A: Chemistry; 251; 8-2013; 113-117
1010-6030
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://www.sciencedirect.com/science/article/pii/S1010603012005035
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2012.10.016
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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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