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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/60938
Ver los metadatos del registro completo
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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 Técnicas2025-09-03T09:54:31Zoai: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:34982025-09-03 09:54:31.95CONICET 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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1842269290285236224 |
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13.13397 |