Synthesis of macroporous polymers with radical scavenging properties by immobilization of polyphenolic compounds

Autores
Arrua, Ruben Dario; Basbus, Juan Felipe; Strumia, Miriam Cristina; Alvarez, Cecilia Ines; Nazareno, Mónica Azucena
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Solid phase radical scavengers have been prepared by the immobilization of antioxidant (AOX) compounds on macroporous polymers. Poly(glycidylmethacrylate- co-trimethylolpropane trimethacrylate) [poly(GMA-TRIM)] and poly(N-acryloyl- tris(hydroxymethyl)aminomethane-co-glycidylmethacrylate-co-N, N′-methylenebisacrylamide) [poly(NAT-GMA-BIS)] were prepared by free radical polymerization using a mixture of dimethylsulfoxide (DMSO)- poly(ethyleneglycol) 6000 (PEG 6000) as a porogenic solvent. The polymers were aminated with ethylenediamine (EDA) and the linkage of the polyphenolic compounds (gallic and caffeic acids) was carried out by two different approaches: through N,N′-dicyclohexylcarbodiimide/4-dimethylaminepyridine (DCC/DMAP) system (one-step method) or through the previous formation of the acyl chloride of the polyphenolic compounds and subsequent amidation reaction (two-step method). The available phenolic groups on the macroporous polymers were determined using the Folin-Ciocalteu method; the radical scavenging properties of the materials prepared were evaluated using the radical species 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and 2,2′-azino-bis-[3- ethylbenzothiazoline-6-sulfonic acid] radical cation (ABTS +). From the results, higher antiradical capacities were obtained with the polymers in which the immobilization of the antioxidant molecules was performed through the two-step method. The polymeric networks prepared in this work yielded up to 13.2 μmol AOX/g of dry polymer, which allowed a quantitative removal of the radicals tested in less than 30 min. © 2012 Elsevier Ltd. All rights reserved.
Fil: Arrua, Ruben Dario. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Basbus, Juan Felipe. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Strumia, Miriam Cristina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Alvarez, Cecilia Ines. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas; Argentina. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; Argentina
Fil: Nazareno, Mónica Azucena. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro de Investigaciones y Transferencia de Santiago del Estero. Universidad Nacional de Santiago del Estero. Centro de Investigaciones y Transferencia de Santiago del Estero; Argentina
Materia
ANTIOXIDANTS
ANTIRADICAL ACTIVITY
MACROPOROUS POLYMERS
PHENOLIC COMPOUNDS
POLYPHENOLS
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:11336/150287
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/150287
network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Synthesis of macroporous polymers with radical scavenging properties by immobilization of polyphenolic compoundsArrua, Ruben DarioBasbus, Juan FelipeStrumia, Miriam CristinaAlvarez, Cecilia InesNazareno, Mónica AzucenaANTIOXIDANTSANTIRADICAL ACTIVITYMACROPOROUS POLYMERSPHENOLIC COMPOUNDSPOLYPHENOLShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Solid phase radical scavengers have been prepared by the immobilization of antioxidant (AOX) compounds on macroporous polymers. Poly(glycidylmethacrylate- co-trimethylolpropane trimethacrylate) [poly(GMA-TRIM)] and poly(N-acryloyl- tris(hydroxymethyl)aminomethane-co-glycidylmethacrylate-co-N, N′-methylenebisacrylamide) [poly(NAT-GMA-BIS)] were prepared by free radical polymerization using a mixture of dimethylsulfoxide (DMSO)- poly(ethyleneglycol) 6000 (PEG 6000) as a porogenic solvent. The polymers were aminated with ethylenediamine (EDA) and the linkage of the polyphenolic compounds (gallic and caffeic acids) was carried out by two different approaches: through N,N′-dicyclohexylcarbodiimide/4-dimethylaminepyridine (DCC/DMAP) system (one-step method) or through the previous formation of the acyl chloride of the polyphenolic compounds and subsequent amidation reaction (two-step method). The available phenolic groups on the macroporous polymers were determined using the Folin-Ciocalteu method; the radical scavenging properties of the materials prepared were evaluated using the radical species 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and 2,2′-azino-bis-[3- ethylbenzothiazoline-6-sulfonic acid] radical cation (ABTS +). From the results, higher antiradical capacities were obtained with the polymers in which the immobilization of the antioxidant molecules was performed through the two-step method. The polymeric networks prepared in this work yielded up to 13.2 μmol AOX/g of dry polymer, which allowed a quantitative removal of the radicals tested in less than 30 min. © 2012 Elsevier Ltd. All rights reserved.Fil: Arrua, Ruben Dario. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaFil: Basbus, Juan Felipe. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Strumia, Miriam Cristina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Alvarez, Cecilia Ines. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas; Argentina. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; ArgentinaFil: Nazareno, Mónica Azucena. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro de Investigaciones y Transferencia de Santiago del Estero. Universidad Nacional de Santiago del Estero. Centro de Investigaciones y Transferencia de Santiago del Estero; ArgentinaElsevier Science2012-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/150287Arrua, Ruben Dario; Basbus, Juan Felipe; Strumia, Miriam Cristina; Alvarez, Cecilia Ines; Nazareno, Mónica Azucena; Synthesis of macroporous polymers with radical scavenging properties by immobilization of polyphenolic compounds; Elsevier Science; Reactive & Functional Polymers; 72; 11; 11-2012; 807-8131381-5148CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.reactfunctpolym.2012.07.017info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S1381514812002143info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:51:07Zoai:ri.conicet.gov.ar:11336/150287instacron: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:34982025-10-15 14:51:07.334CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of macroporous polymers with radical scavenging properties by immobilization of polyphenolic compounds
title Synthesis of macroporous polymers with radical scavenging properties by immobilization of polyphenolic compounds
spellingShingle Synthesis of macroporous polymers with radical scavenging properties by immobilization of polyphenolic compounds
Arrua, Ruben Dario
ANTIOXIDANTS
ANTIRADICAL ACTIVITY
MACROPOROUS POLYMERS
PHENOLIC COMPOUNDS
POLYPHENOLS
title_short Synthesis of macroporous polymers with radical scavenging properties by immobilization of polyphenolic compounds
title_full Synthesis of macroporous polymers with radical scavenging properties by immobilization of polyphenolic compounds
title_fullStr Synthesis of macroporous polymers with radical scavenging properties by immobilization of polyphenolic compounds
title_full_unstemmed Synthesis of macroporous polymers with radical scavenging properties by immobilization of polyphenolic compounds
title_sort Synthesis of macroporous polymers with radical scavenging properties by immobilization of polyphenolic compounds
dc.creator.none.fl_str_mv Arrua, Ruben Dario
Basbus, Juan Felipe
Strumia, Miriam Cristina
Alvarez, Cecilia Ines
Nazareno, Mónica Azucena
author Arrua, Ruben Dario
author_facet Arrua, Ruben Dario
Basbus, Juan Felipe
Strumia, Miriam Cristina
Alvarez, Cecilia Ines
Nazareno, Mónica Azucena
author_role author
author2 Basbus, Juan Felipe
Strumia, Miriam Cristina
Alvarez, Cecilia Ines
Nazareno, Mónica Azucena
author2_role author
author
author
author
dc.subject.none.fl_str_mv ANTIOXIDANTS
ANTIRADICAL ACTIVITY
MACROPOROUS POLYMERS
PHENOLIC COMPOUNDS
POLYPHENOLS
topic ANTIOXIDANTS
ANTIRADICAL ACTIVITY
MACROPOROUS POLYMERS
PHENOLIC COMPOUNDS
POLYPHENOLS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Solid phase radical scavengers have been prepared by the immobilization of antioxidant (AOX) compounds on macroporous polymers. Poly(glycidylmethacrylate- co-trimethylolpropane trimethacrylate) [poly(GMA-TRIM)] and poly(N-acryloyl- tris(hydroxymethyl)aminomethane-co-glycidylmethacrylate-co-N, N′-methylenebisacrylamide) [poly(NAT-GMA-BIS)] were prepared by free radical polymerization using a mixture of dimethylsulfoxide (DMSO)- poly(ethyleneglycol) 6000 (PEG 6000) as a porogenic solvent. The polymers were aminated with ethylenediamine (EDA) and the linkage of the polyphenolic compounds (gallic and caffeic acids) was carried out by two different approaches: through N,N′-dicyclohexylcarbodiimide/4-dimethylaminepyridine (DCC/DMAP) system (one-step method) or through the previous formation of the acyl chloride of the polyphenolic compounds and subsequent amidation reaction (two-step method). The available phenolic groups on the macroporous polymers were determined using the Folin-Ciocalteu method; the radical scavenging properties of the materials prepared were evaluated using the radical species 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and 2,2′-azino-bis-[3- ethylbenzothiazoline-6-sulfonic acid] radical cation (ABTS +). From the results, higher antiradical capacities were obtained with the polymers in which the immobilization of the antioxidant molecules was performed through the two-step method. The polymeric networks prepared in this work yielded up to 13.2 μmol AOX/g of dry polymer, which allowed a quantitative removal of the radicals tested in less than 30 min. © 2012 Elsevier Ltd. All rights reserved.
Fil: Arrua, Ruben Dario. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Basbus, Juan Felipe. Universidad Nacional de Santiago del Estero. Facultad de Agronomía y Agroindustrias. Instituto de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Strumia, Miriam Cristina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Alvarez, Cecilia Ines. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas; Argentina. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; Argentina
Fil: Nazareno, Mónica Azucena. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro de Investigaciones y Transferencia de Santiago del Estero. Universidad Nacional de Santiago del Estero. Centro de Investigaciones y Transferencia de Santiago del Estero; Argentina
description Solid phase radical scavengers have been prepared by the immobilization of antioxidant (AOX) compounds on macroporous polymers. Poly(glycidylmethacrylate- co-trimethylolpropane trimethacrylate) [poly(GMA-TRIM)] and poly(N-acryloyl- tris(hydroxymethyl)aminomethane-co-glycidylmethacrylate-co-N, N′-methylenebisacrylamide) [poly(NAT-GMA-BIS)] were prepared by free radical polymerization using a mixture of dimethylsulfoxide (DMSO)- poly(ethyleneglycol) 6000 (PEG 6000) as a porogenic solvent. The polymers were aminated with ethylenediamine (EDA) and the linkage of the polyphenolic compounds (gallic and caffeic acids) was carried out by two different approaches: through N,N′-dicyclohexylcarbodiimide/4-dimethylaminepyridine (DCC/DMAP) system (one-step method) or through the previous formation of the acyl chloride of the polyphenolic compounds and subsequent amidation reaction (two-step method). The available phenolic groups on the macroporous polymers were determined using the Folin-Ciocalteu method; the radical scavenging properties of the materials prepared were evaluated using the radical species 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and 2,2′-azino-bis-[3- ethylbenzothiazoline-6-sulfonic acid] radical cation (ABTS +). From the results, higher antiradical capacities were obtained with the polymers in which the immobilization of the antioxidant molecules was performed through the two-step method. The polymeric networks prepared in this work yielded up to 13.2 μmol AOX/g of dry polymer, which allowed a quantitative removal of the radicals tested in less than 30 min. © 2012 Elsevier Ltd. All rights reserved.
publishDate 2012
dc.date.none.fl_str_mv 2012-11
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/11336/150287
Arrua, Ruben Dario; Basbus, Juan Felipe; Strumia, Miriam Cristina; Alvarez, Cecilia Ines; Nazareno, Mónica Azucena; Synthesis of macroporous polymers with radical scavenging properties by immobilization of polyphenolic compounds; Elsevier Science; Reactive & Functional Polymers; 72; 11; 11-2012; 807-813
1381-5148
CONICET Digital
CONICET
url http://hdl.handle.net/11336/150287
identifier_str_mv Arrua, Ruben Dario; Basbus, Juan Felipe; Strumia, Miriam Cristina; Alvarez, Cecilia Ines; Nazareno, Mónica Azucena; Synthesis of macroporous polymers with radical scavenging properties by immobilization of polyphenolic compounds; Elsevier Science; Reactive & Functional Polymers; 72; 11; 11-2012; 807-813
1381-5148
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.reactfunctpolym.2012.07.017
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S1381514812002143
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
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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