Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants

Autores
Gruber, Nadia; Orelli, Liliana Raquel; Minnelli, Cristina; Mangano, Luca; Laudadio, Emiliano; Mobbili, Giovanna; Stipa, Pierluigi
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The potential of nitrones (N-oxides) as therapeutic antioxidants is due to their ability to counteract oxidative stress, mainly attributed to their action as radical scavengers toward C- and O-centered radicals. Among them, nitrones from the amidinoquinoxaline series resulted in interesting derivatives, due to the ease with which it is possible to introduce proper substituents within their structure in order to modulate their lipophilicity. The goal is to obtain lipophilic antioxidants that are able to interact with cell membranes and, at the same time, enough hydrophilic to neutralize those radicals present in a water compartment. In this work, the antioxidant efficacy of a series of amidinoquinoxaline nitrones has been evaluated regarding the oxidation of 2-deoxyribose and lipid peroxidation. The results have been rationalized on the basis of the different possible mechanisms involved, depending on some of their properties, such as lipophilicity, the ability to scavenge free radicals, and to undergo single electron transfer (SET) reactions.
Fil: Gruber, Nadia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Orelli, Liliana Raquel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Minnelli, Cristina. Università Politecnica delle Marche; Italia
Fil: Mangano, Luca. F. Hoffmann-la Roche Ag; Suiza
Fil: Laudadio, Emiliano. Università Politecnica delle Marche; Italia
Fil: Mobbili, Giovanna. Università Politecnica delle Marche; Italia
Fil: Stipa, Pierluigi. Università Politecnica delle Marche; Italia
Materia
ANTIOXIDANTS
NITRONES
SPIN TRAPPING
ROS
DFT
FREE RADICALS
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:11336/150063
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Amidinoquinoxaline-Based Nitrones as Lipophilic AntioxidantsGruber, NadiaOrelli, Liliana RaquelMinnelli, CristinaMangano, LucaLaudadio, EmilianoMobbili, GiovannaStipa, PierluigiANTIOXIDANTSNITRONESSPIN TRAPPINGROSDFTFREE RADICALShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The potential of nitrones (N-oxides) as therapeutic antioxidants is due to their ability to counteract oxidative stress, mainly attributed to their action as radical scavengers toward C- and O-centered radicals. Among them, nitrones from the amidinoquinoxaline series resulted in interesting derivatives, due to the ease with which it is possible to introduce proper substituents within their structure in order to modulate their lipophilicity. The goal is to obtain lipophilic antioxidants that are able to interact with cell membranes and, at the same time, enough hydrophilic to neutralize those radicals present in a water compartment. In this work, the antioxidant efficacy of a series of amidinoquinoxaline nitrones has been evaluated regarding the oxidation of 2-deoxyribose and lipid peroxidation. The results have been rationalized on the basis of the different possible mechanisms involved, depending on some of their properties, such as lipophilicity, the ability to scavenge free radicals, and to undergo single electron transfer (SET) reactions.Fil: Gruber, Nadia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Orelli, Liliana Raquel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Minnelli, Cristina. Università Politecnica delle Marche; ItaliaFil: Mangano, Luca. F. Hoffmann-la Roche Ag; SuizaFil: Laudadio, Emiliano. Università Politecnica delle Marche; ItaliaFil: Mobbili, Giovanna. Università Politecnica delle Marche; ItaliaFil: Stipa, Pierluigi. Università Politecnica delle Marche; ItaliaMDPI2021-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/150063Gruber, Nadia; Orelli, Liliana Raquel; Minnelli, Cristina; Mangano, Luca; Laudadio, Emiliano; et al.; Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants; MDPI; Antioxidants; 10; 8; 8-2021; 1185-11952076-39212076-3921CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3390/antiox10081185info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/2076-3921/10/8/1185info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:50:53Zoai:ri.conicet.gov.ar:11336/150063instacron: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 09:50:53.749CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants
title Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants
spellingShingle Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants
Gruber, Nadia
ANTIOXIDANTS
NITRONES
SPIN TRAPPING
ROS
DFT
FREE RADICALS
title_short Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants
title_full Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants
title_fullStr Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants
title_full_unstemmed Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants
title_sort Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants
dc.creator.none.fl_str_mv Gruber, Nadia
Orelli, Liliana Raquel
Minnelli, Cristina
Mangano, Luca
Laudadio, Emiliano
Mobbili, Giovanna
Stipa, Pierluigi
author Gruber, Nadia
author_facet Gruber, Nadia
Orelli, Liliana Raquel
Minnelli, Cristina
Mangano, Luca
Laudadio, Emiliano
Mobbili, Giovanna
Stipa, Pierluigi
author_role author
author2 Orelli, Liliana Raquel
Minnelli, Cristina
Mangano, Luca
Laudadio, Emiliano
Mobbili, Giovanna
Stipa, Pierluigi
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv ANTIOXIDANTS
NITRONES
SPIN TRAPPING
ROS
DFT
FREE RADICALS
topic ANTIOXIDANTS
NITRONES
SPIN TRAPPING
ROS
DFT
FREE RADICALS
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 potential of nitrones (N-oxides) as therapeutic antioxidants is due to their ability to counteract oxidative stress, mainly attributed to their action as radical scavengers toward C- and O-centered radicals. Among them, nitrones from the amidinoquinoxaline series resulted in interesting derivatives, due to the ease with which it is possible to introduce proper substituents within their structure in order to modulate their lipophilicity. The goal is to obtain lipophilic antioxidants that are able to interact with cell membranes and, at the same time, enough hydrophilic to neutralize those radicals present in a water compartment. In this work, the antioxidant efficacy of a series of amidinoquinoxaline nitrones has been evaluated regarding the oxidation of 2-deoxyribose and lipid peroxidation. The results have been rationalized on the basis of the different possible mechanisms involved, depending on some of their properties, such as lipophilicity, the ability to scavenge free radicals, and to undergo single electron transfer (SET) reactions.
Fil: Gruber, Nadia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Orelli, Liliana Raquel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Minnelli, Cristina. Università Politecnica delle Marche; Italia
Fil: Mangano, Luca. F. Hoffmann-la Roche Ag; Suiza
Fil: Laudadio, Emiliano. Università Politecnica delle Marche; Italia
Fil: Mobbili, Giovanna. Università Politecnica delle Marche; Italia
Fil: Stipa, Pierluigi. Università Politecnica delle Marche; Italia
description The potential of nitrones (N-oxides) as therapeutic antioxidants is due to their ability to counteract oxidative stress, mainly attributed to their action as radical scavengers toward C- and O-centered radicals. Among them, nitrones from the amidinoquinoxaline series resulted in interesting derivatives, due to the ease with which it is possible to introduce proper substituents within their structure in order to modulate their lipophilicity. The goal is to obtain lipophilic antioxidants that are able to interact with cell membranes and, at the same time, enough hydrophilic to neutralize those radicals present in a water compartment. In this work, the antioxidant efficacy of a series of amidinoquinoxaline nitrones has been evaluated regarding the oxidation of 2-deoxyribose and lipid peroxidation. The results have been rationalized on the basis of the different possible mechanisms involved, depending on some of their properties, such as lipophilicity, the ability to scavenge free radicals, and to undergo single electron transfer (SET) reactions.
publishDate 2021
dc.date.none.fl_str_mv 2021-08
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/11336/150063
Gruber, Nadia; Orelli, Liliana Raquel; Minnelli, Cristina; Mangano, Luca; Laudadio, Emiliano; et al.; Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants; MDPI; Antioxidants; 10; 8; 8-2021; 1185-1195
2076-3921
2076-3921
CONICET Digital
CONICET
url http://hdl.handle.net/11336/150063
identifier_str_mv Gruber, Nadia; Orelli, Liliana Raquel; Minnelli, Cristina; Mangano, Luca; Laudadio, Emiliano; et al.; Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants; MDPI; Antioxidants; 10; 8; 8-2021; 1185-1195
2076-3921
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3390/antiox10081185
info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/2076-3921/10/8/1185
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
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
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
_version_ 1842269060475125760
score 13.13397

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