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

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...

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Autores: Natera, Jose Eduardo, Gatica, Eduardo Antonio, Challier, Cecilia, Possetto, David Ivan, Massad, Walter Alfredo, Miskoski, Sandra, Pajares, Adriana Mabel, Garcia, Norman Andino
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2015
País:Argentina
Recursos:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/60938
Acesso em linha:http://hdl.handle.net/11336/60938
Access Level:acceso abierto
Palavra-chave:NICLOSAMIDE
PHOTODEGRADATION
PHOTOOXIDATION
REACTIVE OXYGEN SPECIES
RIBOFLAVIN
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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oai_identifier_str oai:ri.conicet.gov.ar:11336/60938
network_acronym_str AR
network_name_str Argentina
repository_id_str
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
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic NICLOSAMIDE
PHOTODEGRADATION
PHOTOOXIDATION
REACTIVE OXYGEN SPECIES
RIBOFLAVIN
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
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
_version_ 1799195370445602816
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 Técnicas2024-05-08T13:50:27Zoai: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:34982024-05-08 13:50:27.433CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
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