Cyclodextrine-nanoencapsulation of niclosamide: Water solubility and meaningful enhancement of visible-light—Mediated sensitized photodegradation of the drug

Autores
Gatica, Eduardo Antonio; Natera, Jose Eduardo; Pajares, Adriana Mabel; Gambetta, Carolina; Sancho, Matias Israel; Massad, Walter Alfredo; Garcia, Norman Andino
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A kinetic and mechanistic study of the daylight-mediated photooxidation of the multifunctional drug Niclosamide (NSD) was carried out in aqueous solutions. NSD is a frequent contaminant suspended in natural waters. The aqueous dissolution of the practically insoluble NSD was driven by the presence of 2-hydrxypropyl-β-cyclodextrin (HPβCD). The already proposed formation of an inclusion complex between NSD-HPβCD was confirmed through theoretical studies. NSD-nanoencapsulation within the oligosaccharide occurs with a 1:2 stoichiometry, being the drug embedded into a cavity of two HPβCD molecules, in a so called head-to-head orientation. The Reactive Oxygen Species singlet molecular oxygen, superoxide radical anion and hydrogen peroxide, generated through the visible-light absorber sensitizers Riboflavin and Rose Bengal, are effectively intercepted by the encapsulated biocide and contribute to its photodegradation. The overall NSD photooxidation rate, determined through oxygen consumption indicates that the process is relatively highly efficient in the microheterogeneous aqueous media as compared to NSD in MeOH solution, and to phenol (PHE) in pure water. The paradigmatic water-contaminant PHE was taken a as reference in order to evaluate the persistence of the NSD under photosensitized irradiation in aqueous medium. The photooxidation mechanism of NSD is affected by cyclodextrin complexation, due to dynamic limitations, electrostatic interactions and pH changes upon NSD dissolution in aqueous HPβCD. In this sense, the NSD-HPβCD complex can be seen as a sort of nanoreactor that enables the photodegradation of the biocide in water, under daylight conditions.
Fil: Gatica, Eduardo Antonio. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Natera, Jose Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. 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 "San Juan Bosco". Facultad de Ingeniería - Sede Comodoro; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de la Patagonia Austral. Unidad Académica Río Gallegos; Argentina
Fil: Gambetta, Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Sancho, Matias Israel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina
Fil: Massad, Walter Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
Cyclodextrin Encapsulation
Niclosamide
Photooxidation
Photosensitization
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:11336/38557
Acceder
id CONICETDig_b4ee09322e015f844878240456205da3
oai_identifier_str oai:ri.conicet.gov.ar:11336/38557
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Cyclodextrine-nanoencapsulation of niclosamide: Water solubility and meaningful enhancement of visible-light—Mediated sensitized photodegradation of the drugGatica, Eduardo AntonioNatera, Jose EduardoPajares, Adriana MabelGambetta, CarolinaSancho, Matias IsraelMassad, Walter AlfredoGarcia, Norman AndinoCyclodextrin EncapsulationNiclosamidePhotooxidationPhotosensitizationReactive Oxygen SpeciesRiboflavinhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A kinetic and mechanistic study of the daylight-mediated photooxidation of the multifunctional drug Niclosamide (NSD) was carried out in aqueous solutions. NSD is a frequent contaminant suspended in natural waters. The aqueous dissolution of the practically insoluble NSD was driven by the presence of 2-hydrxypropyl-β-cyclodextrin (HPβCD). The already proposed formation of an inclusion complex between NSD-HPβCD was confirmed through theoretical studies. NSD-nanoencapsulation within the oligosaccharide occurs with a 1:2 stoichiometry, being the drug embedded into a cavity of two HPβCD molecules, in a so called head-to-head orientation. The Reactive Oxygen Species singlet molecular oxygen, superoxide radical anion and hydrogen peroxide, generated through the visible-light absorber sensitizers Riboflavin and Rose Bengal, are effectively intercepted by the encapsulated biocide and contribute to its photodegradation. The overall NSD photooxidation rate, determined through oxygen consumption indicates that the process is relatively highly efficient in the microheterogeneous aqueous media as compared to NSD in MeOH solution, and to phenol (PHE) in pure water. The paradigmatic water-contaminant PHE was taken a as reference in order to evaluate the persistence of the NSD under photosensitized irradiation in aqueous medium. The photooxidation mechanism of NSD is affected by cyclodextrin complexation, due to dynamic limitations, electrostatic interactions and pH changes upon NSD dissolution in aqueous HPβCD. In this sense, the NSD-HPβCD complex can be seen as a sort of nanoreactor that enables the photodegradation of the biocide in water, under daylight conditions.Fil: Gatica, Eduardo Antonio. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Natera, Jose Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Pajares, Adriana Mabel. Universidad Nacional de la Patagonia "San Juan Bosco". Facultad de Ingeniería - Sede Comodoro; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de la Patagonia Austral. Unidad Académica Río Gallegos; ArgentinaFil: Gambetta, Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Sancho, Matias Israel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; ArgentinaFil: Massad, Walter Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaElsevier Science Sa2017-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/38557Gatica, Eduardo Antonio; Natera, Jose Eduardo; Pajares, Adriana Mabel; Gambetta, Carolina; Sancho, Matias Israel; et al.; Cyclodextrine-nanoencapsulation of niclosamide: Water solubility and meaningful enhancement of visible-light—Mediated sensitized photodegradation of the drug; Elsevier Science Sa; Journal of Photochemistry and Photobiology A: Chemistry; 348; 11-2017; 295-3041010-6030CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1010603017306457info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2017.08.015info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:35:31Zoai:ri.conicet.gov.ar:11336/38557instacron: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 09:35:32.078CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Cyclodextrine-nanoencapsulation of niclosamide: Water solubility and meaningful enhancement of visible-light—Mediated sensitized photodegradation of the drug
title Cyclodextrine-nanoencapsulation of niclosamide: Water solubility and meaningful enhancement of visible-light—Mediated sensitized photodegradation of the drug
spellingShingle Cyclodextrine-nanoencapsulation of niclosamide: Water solubility and meaningful enhancement of visible-light—Mediated sensitized photodegradation of the drug
Gatica, Eduardo Antonio
Cyclodextrin Encapsulation
Niclosamide
Photooxidation
Photosensitization
Reactive Oxygen Species
Riboflavin
title_short Cyclodextrine-nanoencapsulation of niclosamide: Water solubility and meaningful enhancement of visible-light—Mediated sensitized photodegradation of the drug
title_full Cyclodextrine-nanoencapsulation of niclosamide: Water solubility and meaningful enhancement of visible-light—Mediated sensitized photodegradation of the drug
title_fullStr Cyclodextrine-nanoencapsulation of niclosamide: Water solubility and meaningful enhancement of visible-light—Mediated sensitized photodegradation of the drug
title_full_unstemmed Cyclodextrine-nanoencapsulation of niclosamide: Water solubility and meaningful enhancement of visible-light—Mediated sensitized photodegradation of the drug
title_sort Cyclodextrine-nanoencapsulation of niclosamide: Water solubility and meaningful enhancement of visible-light—Mediated sensitized photodegradation of the drug
dc.creator.none.fl_str_mv Gatica, Eduardo Antonio
Natera, Jose Eduardo
Pajares, Adriana Mabel
Gambetta, Carolina
Sancho, Matias Israel
Massad, Walter Alfredo
Garcia, Norman Andino
author Gatica, Eduardo Antonio
author_facet Gatica, Eduardo Antonio
Natera, Jose Eduardo
Pajares, Adriana Mabel
Gambetta, Carolina
Sancho, Matias Israel
Massad, Walter Alfredo
Garcia, Norman Andino
author_role author
author2 Natera, Jose Eduardo
Pajares, Adriana Mabel
Gambetta, Carolina
Sancho, Matias Israel
Massad, Walter Alfredo
Garcia, Norman Andino
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Cyclodextrin Encapsulation
Niclosamide
Photooxidation
Photosensitization
Reactive Oxygen Species
Riboflavin
topic Cyclodextrin Encapsulation
Niclosamide
Photooxidation
Photosensitization
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 A kinetic and mechanistic study of the daylight-mediated photooxidation of the multifunctional drug Niclosamide (NSD) was carried out in aqueous solutions. NSD is a frequent contaminant suspended in natural waters. The aqueous dissolution of the practically insoluble NSD was driven by the presence of 2-hydrxypropyl-β-cyclodextrin (HPβCD). The already proposed formation of an inclusion complex between NSD-HPβCD was confirmed through theoretical studies. NSD-nanoencapsulation within the oligosaccharide occurs with a 1:2 stoichiometry, being the drug embedded into a cavity of two HPβCD molecules, in a so called head-to-head orientation. The Reactive Oxygen Species singlet molecular oxygen, superoxide radical anion and hydrogen peroxide, generated through the visible-light absorber sensitizers Riboflavin and Rose Bengal, are effectively intercepted by the encapsulated biocide and contribute to its photodegradation. The overall NSD photooxidation rate, determined through oxygen consumption indicates that the process is relatively highly efficient in the microheterogeneous aqueous media as compared to NSD in MeOH solution, and to phenol (PHE) in pure water. The paradigmatic water-contaminant PHE was taken a as reference in order to evaluate the persistence of the NSD under photosensitized irradiation in aqueous medium. The photooxidation mechanism of NSD is affected by cyclodextrin complexation, due to dynamic limitations, electrostatic interactions and pH changes upon NSD dissolution in aqueous HPβCD. In this sense, the NSD-HPβCD complex can be seen as a sort of nanoreactor that enables the photodegradation of the biocide in water, under daylight conditions.
Fil: Gatica, Eduardo Antonio. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Natera, Jose Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. 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 "San Juan Bosco". Facultad de Ingeniería - Sede Comodoro; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de la Patagonia Austral. Unidad Académica Río Gallegos; Argentina
Fil: Gambetta, Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Sancho, Matias Israel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina
Fil: Massad, Walter Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description A kinetic and mechanistic study of the daylight-mediated photooxidation of the multifunctional drug Niclosamide (NSD) was carried out in aqueous solutions. NSD is a frequent contaminant suspended in natural waters. The aqueous dissolution of the practically insoluble NSD was driven by the presence of 2-hydrxypropyl-β-cyclodextrin (HPβCD). The already proposed formation of an inclusion complex between NSD-HPβCD was confirmed through theoretical studies. NSD-nanoencapsulation within the oligosaccharide occurs with a 1:2 stoichiometry, being the drug embedded into a cavity of two HPβCD molecules, in a so called head-to-head orientation. The Reactive Oxygen Species singlet molecular oxygen, superoxide radical anion and hydrogen peroxide, generated through the visible-light absorber sensitizers Riboflavin and Rose Bengal, are effectively intercepted by the encapsulated biocide and contribute to its photodegradation. The overall NSD photooxidation rate, determined through oxygen consumption indicates that the process is relatively highly efficient in the microheterogeneous aqueous media as compared to NSD in MeOH solution, and to phenol (PHE) in pure water. The paradigmatic water-contaminant PHE was taken a as reference in order to evaluate the persistence of the NSD under photosensitized irradiation in aqueous medium. The photooxidation mechanism of NSD is affected by cyclodextrin complexation, due to dynamic limitations, electrostatic interactions and pH changes upon NSD dissolution in aqueous HPβCD. In this sense, the NSD-HPβCD complex can be seen as a sort of nanoreactor that enables the photodegradation of the biocide in water, under daylight conditions.
publishDate 2017
dc.date.none.fl_str_mv 2017-11
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/11336/38557
Gatica, Eduardo Antonio; Natera, Jose Eduardo; Pajares, Adriana Mabel; Gambetta, Carolina; Sancho, Matias Israel; et al.; Cyclodextrine-nanoencapsulation of niclosamide: Water solubility and meaningful enhancement of visible-light—Mediated sensitized photodegradation of the drug; Elsevier Science Sa; Journal of Photochemistry and Photobiology A: Chemistry; 348; 11-2017; 295-304
1010-6030
CONICET Digital
CONICET
url http://hdl.handle.net/11336/38557
identifier_str_mv Gatica, Eduardo Antonio; Natera, Jose Eduardo; Pajares, Adriana Mabel; Gambetta, Carolina; Sancho, Matias Israel; et al.; Cyclodextrine-nanoencapsulation of niclosamide: Water solubility and meaningful enhancement of visible-light—Mediated sensitized photodegradation of the drug; Elsevier Science Sa; Journal of Photochemistry and Photobiology A: Chemistry; 348; 11-2017; 295-304
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/S1010603017306457
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2017.08.015
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
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science Sa
publisher.none.fl_str_mv Elsevier Science Sa
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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