On the photooxidation of the multifunctional drug niclosamide. A kinetic study in the presence of vitamin B2 and visible light

Autores
Natera, Jose Eduardo; Gatica, Eduardo Antonio; Challier, Cecilia; Possetto, David Ivan; Massad, Walter Alfredo; Miskoski, Sandra; Pajares, Adriana Mabel; Garcia, Norman Andino
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The multifunctional drug niclosamide (NSD), extensively employed therapeutically, is a frequent pollutant of surface waters. Considering the environmental importance of photodegradative processes for this type of contaminant, the kinetic and mechanistic aspects of the possible visible-light-mediated photooxidation of NSD were studied under naturalistic conditions. Methods: The visible-light absorber riboflavin (vitamin B2) was employed as a photosensitizer. The vitamin can usually be found in natural waters and is the most common endogenous photosensitizer in mammals. The interaction of NSD with electronically excited states of Rf and with photogenerated reactive oxygen species (ROS) was evaluated through conventional UV spectroscopy, laser flash photolysis, time-resolved phosphorescence detection of singlet molecular oxygen (O2(1Δg)), and polarographic dosage of dissolved oxygen. Results: Ground state NSD quenched the long-lived triplet excited state of Rf (3Rf*) and the photogenerated ROS (O2(1Δg)) and superoxide radical anion (O2•−). As a result, NSD was photooxidized. The rate constants for the interaction NSD–O2(1Δg) are particularly low, in the order of 106/M/s, although the whole interaction is attributable to a pure reactive process. The O2(1Δg) quenching was faster in alkaline medium, favored by the ionization of the NSD phenolic group. Under Rf-photosensitization, NSD was degraded very much more rapidly than phenol, the latter being considered a paradigmatic water-contaminant model compound. NSD may behave as an antioxidant in bio-environments, as demonstrated employing the photooxidizable amino acid tryptophan as a relevant biological target. Discussion: The results indicate that a O2•−-mediated process is the main route for the Rf-sensitized photooxidation of NSD. Photodegradation of the biocide in the presence and absence of phenol and tryptophan was quantitatively evaluated, discussed, and interpreted in terms of competitive quenching processes of3Rf*, O2(1Δg), and O2•− by the substrates.
Fil: Natera, Jose Eduardo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Gatica, Eduardo Antonio. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Challier, Cecilia. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Possetto, David Ivan. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Miskoski, Sandra. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Pajares, Adriana Mabel. Universidad Nacional de la Patagonia; Argentina
Fil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Materia
NICLOSAMIDE
PHOTODEGRADATION
PHOTOOXIDATION
REACTIVE OXYGEN SPECIES
RIBOFLAVIN
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:11336/60938
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/60938
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling On the photooxidation of the multifunctional drug niclosamide. A kinetic study in the presence of vitamin B2 and visible lightNatera, Jose EduardoGatica, Eduardo AntonioChallier, CeciliaPossetto, David IvanMassad, Walter AlfredoMiskoski, SandraPajares, Adriana MabelGarcia, Norman AndinoNICLOSAMIDEPHOTODEGRADATIONPHOTOOXIDATIONREACTIVE OXYGEN SPECIESRIBOFLAVINhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The multifunctional drug niclosamide (NSD), extensively employed therapeutically, is a frequent pollutant of surface waters. Considering the environmental importance of photodegradative processes for this type of contaminant, the kinetic and mechanistic aspects of the possible visible-light-mediated photooxidation of NSD were studied under naturalistic conditions. Methods: The visible-light absorber riboflavin (vitamin B2) was employed as a photosensitizer. The vitamin can usually be found in natural waters and is the most common endogenous photosensitizer in mammals. The interaction of NSD with electronically excited states of Rf and with photogenerated reactive oxygen species (ROS) was evaluated through conventional UV spectroscopy, laser flash photolysis, time-resolved phosphorescence detection of singlet molecular oxygen (O2(1Δg)), and polarographic dosage of dissolved oxygen. Results: Ground state NSD quenched the long-lived triplet excited state of Rf (3Rf*) and the photogenerated ROS (O2(1Δg)) and superoxide radical anion (O2•−). As a result, NSD was photooxidized. The rate constants for the interaction NSD–O2(1Δg) are particularly low, in the order of 106/M/s, although the whole interaction is attributable to a pure reactive process. The O2(1Δg) quenching was faster in alkaline medium, favored by the ionization of the NSD phenolic group. Under Rf-photosensitization, NSD was degraded very much more rapidly than phenol, the latter being considered a paradigmatic water-contaminant model compound. NSD may behave as an antioxidant in bio-environments, as demonstrated employing the photooxidizable amino acid tryptophan as a relevant biological target. Discussion: The results indicate that a O2•−-mediated process is the main route for the Rf-sensitized photooxidation of NSD. Photodegradation of the biocide in the presence and absence of phenol and tryptophan was quantitatively evaluated, discussed, and interpreted in terms of competitive quenching processes of3Rf*, O2(1Δg), and O2•− by the substrates.Fil: Natera, Jose Eduardo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Gatica, Eduardo Antonio. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Challier, Cecilia. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Possetto, David Ivan. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Miskoski, Sandra. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Pajares, Adriana Mabel. Universidad Nacional de la Patagonia; ArgentinaFil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaManey Publishing2015-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/vnd.openxmlformats-officedocument.wordprocessingml.documentapplication/pdfhttp://hdl.handle.net/11336/60938Natera, Jose Eduardo; Gatica, Eduardo Antonio; Challier, Cecilia; Possetto, David Ivan; Massad, Walter Alfredo; et al.; On the photooxidation of the multifunctional drug niclosamide. A kinetic study in the presence of vitamin B2 and visible light; Maney Publishing; Redox Report; 20; 6; 11-2015; 259-2661351-00021743-2928CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.ncbi.nlm.nih.gov/pubmed/25897629info:eu-repo/semantics/altIdentifier/doi/10.1179/1351000215Y.0000000010info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:55:44Zoai:ri.conicet.gov.ar:11336/60938instacron: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 09:55:44.36CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv On the photooxidation of the multifunctional drug niclosamide. A kinetic study in the presence of vitamin B2 and visible light
title On the photooxidation of the multifunctional drug niclosamide. A kinetic study in the presence of vitamin B2 and visible light
spellingShingle On the photooxidation of the multifunctional drug niclosamide. A kinetic study in the presence of vitamin B2 and visible light
Natera, Jose Eduardo
NICLOSAMIDE
PHOTODEGRADATION
PHOTOOXIDATION
REACTIVE OXYGEN SPECIES
RIBOFLAVIN
title_short On the photooxidation of the multifunctional drug niclosamide. A kinetic study in the presence of vitamin B2 and visible light
title_full On the photooxidation of the multifunctional drug niclosamide. A kinetic study in the presence of vitamin B2 and visible light
title_fullStr On the photooxidation of the multifunctional drug niclosamide. A kinetic study in the presence of vitamin B2 and visible light
title_full_unstemmed On the photooxidation of the multifunctional drug niclosamide. A kinetic study in the presence of vitamin B2 and visible light
title_sort On the photooxidation of the multifunctional drug niclosamide. A kinetic study in the presence of vitamin B2 and visible light
dc.creator.none.fl_str_mv Natera, Jose Eduardo
Gatica, Eduardo Antonio
Challier, Cecilia
Possetto, David Ivan
Massad, Walter Alfredo
Miskoski, Sandra
Pajares, Adriana Mabel
Garcia, Norman Andino
author Natera, Jose Eduardo
author_facet Natera, Jose Eduardo
Gatica, Eduardo Antonio
Challier, Cecilia
Possetto, David Ivan
Massad, Walter Alfredo
Miskoski, Sandra
Pajares, Adriana Mabel
Garcia, Norman Andino
author_role author
author2 Gatica, Eduardo Antonio
Challier, Cecilia
Possetto, David Ivan
Massad, Walter Alfredo
Miskoski, Sandra
Pajares, Adriana Mabel
Garcia, Norman Andino
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv NICLOSAMIDE
PHOTODEGRADATION
PHOTOOXIDATION
REACTIVE OXYGEN SPECIES
RIBOFLAVIN
topic NICLOSAMIDE
PHOTODEGRADATION
PHOTOOXIDATION
REACTIVE OXYGEN SPECIES
RIBOFLAVIN
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The multifunctional drug niclosamide (NSD), extensively employed therapeutically, is a frequent pollutant of surface waters. Considering the environmental importance of photodegradative processes for this type of contaminant, the kinetic and mechanistic aspects of the possible visible-light-mediated photooxidation of NSD were studied under naturalistic conditions. Methods: The visible-light absorber riboflavin (vitamin B2) was employed as a photosensitizer. The vitamin can usually be found in natural waters and is the most common endogenous photosensitizer in mammals. The interaction of NSD with electronically excited states of Rf and with photogenerated reactive oxygen species (ROS) was evaluated through conventional UV spectroscopy, laser flash photolysis, time-resolved phosphorescence detection of singlet molecular oxygen (O2(1Δg)), and polarographic dosage of dissolved oxygen. Results: Ground state NSD quenched the long-lived triplet excited state of Rf (3Rf*) and the photogenerated ROS (O2(1Δg)) and superoxide radical anion (O2•−). As a result, NSD was photooxidized. The rate constants for the interaction NSD–O2(1Δg) are particularly low, in the order of 106/M/s, although the whole interaction is attributable to a pure reactive process. The O2(1Δg) quenching was faster in alkaline medium, favored by the ionization of the NSD phenolic group. Under Rf-photosensitization, NSD was degraded very much more rapidly than phenol, the latter being considered a paradigmatic water-contaminant model compound. NSD may behave as an antioxidant in bio-environments, as demonstrated employing the photooxidizable amino acid tryptophan as a relevant biological target. Discussion: The results indicate that a O2•−-mediated process is the main route for the Rf-sensitized photooxidation of NSD. Photodegradation of the biocide in the presence and absence of phenol and tryptophan was quantitatively evaluated, discussed, and interpreted in terms of competitive quenching processes of3Rf*, O2(1Δg), and O2•− by the substrates.
Fil: Natera, Jose Eduardo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Gatica, Eduardo Antonio. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Challier, Cecilia. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Possetto, David Ivan. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Miskoski, Sandra. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Pajares, Adriana Mabel. Universidad Nacional de la Patagonia; Argentina
Fil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
description The multifunctional drug niclosamide (NSD), extensively employed therapeutically, is a frequent pollutant of surface waters. Considering the environmental importance of photodegradative processes for this type of contaminant, the kinetic and mechanistic aspects of the possible visible-light-mediated photooxidation of NSD were studied under naturalistic conditions. Methods: The visible-light absorber riboflavin (vitamin B2) was employed as a photosensitizer. The vitamin can usually be found in natural waters and is the most common endogenous photosensitizer in mammals. The interaction of NSD with electronically excited states of Rf and with photogenerated reactive oxygen species (ROS) was evaluated through conventional UV spectroscopy, laser flash photolysis, time-resolved phosphorescence detection of singlet molecular oxygen (O2(1Δg)), and polarographic dosage of dissolved oxygen. Results: Ground state NSD quenched the long-lived triplet excited state of Rf (3Rf*) and the photogenerated ROS (O2(1Δg)) and superoxide radical anion (O2•−). As a result, NSD was photooxidized. The rate constants for the interaction NSD–O2(1Δg) are particularly low, in the order of 106/M/s, although the whole interaction is attributable to a pure reactive process. The O2(1Δg) quenching was faster in alkaline medium, favored by the ionization of the NSD phenolic group. Under Rf-photosensitization, NSD was degraded very much more rapidly than phenol, the latter being considered a paradigmatic water-contaminant model compound. NSD may behave as an antioxidant in bio-environments, as demonstrated employing the photooxidizable amino acid tryptophan as a relevant biological target. Discussion: The results indicate that a O2•−-mediated process is the main route for the Rf-sensitized photooxidation of NSD. Photodegradation of the biocide in the presence and absence of phenol and tryptophan was quantitatively evaluated, discussed, and interpreted in terms of competitive quenching processes of3Rf*, O2(1Δg), and O2•− by the substrates.
publishDate 2015
dc.date.none.fl_str_mv 2015-11
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/11336/60938
Natera, Jose Eduardo; Gatica, Eduardo Antonio; Challier, Cecilia; Possetto, David Ivan; Massad, Walter Alfredo; et al.; On the photooxidation of the multifunctional drug niclosamide. A kinetic study in the presence of vitamin B2 and visible light; Maney Publishing; Redox Report; 20; 6; 11-2015; 259-266
1351-0002
1743-2928
CONICET Digital
CONICET
url http://hdl.handle.net/11336/60938
identifier_str_mv Natera, Jose Eduardo; Gatica, Eduardo Antonio; Challier, Cecilia; Possetto, David Ivan; Massad, Walter Alfredo; et al.; On the photooxidation of the multifunctional drug niclosamide. A kinetic study in the presence of vitamin B2 and visible light; Maney Publishing; Redox Report; 20; 6; 11-2015; 259-266
1351-0002
1743-2928
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.ncbi.nlm.nih.gov/pubmed/25897629
info:eu-repo/semantics/altIdentifier/doi/10.1179/1351000215Y.0000000010
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/vnd.openxmlformats-officedocument.wordprocessingml.document
application/pdf
dc.publisher.none.fl_str_mv Maney Publishing
publisher.none.fl_str_mv Maney Publishing
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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