Synthesis and Antioxidant Properties of Novel 1,2,3-Triazole-Containing Nitrones

Herein, we report the synthesis and antioxidant capacity of twelve novel 1,2,3-triazole-containing nitrones such as N-(2-(4-aryl-1H-1,2,3-triazol-1-yl)ethylidene)methanamine oxides 8a–f and N-(2-(4-aryl)-1H-1,2,3-triazol-1-yl)ethylidene)-2-methylpropan-2-amine oxides 9a–f, bearing an N-methyl, and a...

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Autores: Hadjipavlou-Litina, Dimitra, Głowacka, Iwona E., Marco-Contelles, José, Piotrowska, Dorota G.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2023
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/306940
Acceso en línea:http://hdl.handle.net/10261/306940
Access Level:acceso abierto
Palabra clave:Antioxidants
oxidative stress
1,2,3-Triazole-containing nitrones
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spelling Synthesis and Antioxidant Properties of Novel 1,2,3-Triazole-Containing NitronesHadjipavlou-Litina, DimitraGłowacka, Iwona E.Marco-Contelles, JoséPiotrowska, Dorota G.Antioxidantsoxidative stress1,2,3-Triazole-containing nitronesHerein, we report the synthesis and antioxidant capacity of twelve novel 1,2,3-triazole-containing nitrones such as N-(2-(4-aryl-1H-1,2,3-triazol-1-yl)ethylidene)methanamine oxides 8a–f and N-(2-(4-aryl)-1H-1,2,3-triazol-1-yl)ethylidene)-2-methylpropan-2-amine oxides 9a–f, bearing an N-methyl, and an N-t-butyl substituent, respectively, at the nitrogen of the nitrone motif. Nitrones 8 and 9 were studied with regard to their antioxidant ability, as well as their ability to inhibit soybean lypoxygenase (LOX), and their in vitro antioxidant activity. For this, we used three different antioxidant assays, such as that featuring the interaction with the water-soluble azo compound AAPH for the inhibition of lipid peroxidation (LP), the competition with the DMSO for scavenging hydroxyl radicals, and the ABTS–decolorization assay. t-Butyl nitrone 9e, bearing the 2,4-difluorophenyl motif, showed a strong LP inhibitory effect (100%), close to the reference compound Trolox (93%), being the most potent LP inhibitor (LPi) of the whole series of tested nitrones. Nitrones 9d, 9e and 9f, bearing the 4-fluorophenyl, 2,4-difluorophenyl, and 4-fluoro-3-methylphenyl motif, respectively, were almost equipotent, and the most potent hydroxyl radical scavengers (~100%), more potent than Trolox (88%), were used as a reference compound. Regarding the LOX inhibition, the most potent inhibitor was the t-butyl substituted nitrone 9f (27 μM), bearing the 4-fluoro-3-methylphenyl motif, being 60-fold less potent than NDGA (0.45 μM), which was used as the standard in this test. The results from the antioxidant determination in the ABTS radical cation (ABTS) decolorization assay were not significant. N-Methyl nitrone 8f, bearing the 4-fluoro-3-methylphenyl motif, was the only promising representative, with a value of 34.3%, followed by nitrone 9f (16%). From the antioxidant analyses, we have identified N-(2-(4-(4-fluoro-3-methylphenyl)-1H-1,2,3-triazol-1-yl)ethylidene)-2-methylpropan-2-amine oxide (9f), bearing t-butyl and 4-fluoro-3-methylphenyl motifs in its structure, as the most balanced and potent antioxidant agent among the tested nitrones, as it was the most potent LOX inhibitor (27 μM), an extremely efficient and potent hydroxyl radical scavenger (99.9%), as well as one of the most potent LPi (87%) and ABTS scavengers (16%).The synthetic part of the project was supported by the Medical University of Lodz internal funds (503/3-014-01/503-31-001)Multidisciplinary Digital Publishing InstituteUniversity of LodzConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2023202320232023info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/306940reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttp://dx.doi.org/10.3390/antiox12010036Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/3069402026-05-22T06:33:51Z
dc.title.none.fl_str_mv Synthesis and Antioxidant Properties of Novel 1,2,3-Triazole-Containing Nitrones
title Synthesis and Antioxidant Properties of Novel 1,2,3-Triazole-Containing Nitrones
spellingShingle Synthesis and Antioxidant Properties of Novel 1,2,3-Triazole-Containing Nitrones
Hadjipavlou-Litina, Dimitra
Antioxidants
oxidative stress
1,2,3-Triazole-containing nitrones
title_short Synthesis and Antioxidant Properties of Novel 1,2,3-Triazole-Containing Nitrones
title_full Synthesis and Antioxidant Properties of Novel 1,2,3-Triazole-Containing Nitrones
title_fullStr Synthesis and Antioxidant Properties of Novel 1,2,3-Triazole-Containing Nitrones
title_full_unstemmed Synthesis and Antioxidant Properties of Novel 1,2,3-Triazole-Containing Nitrones
title_sort Synthesis and Antioxidant Properties of Novel 1,2,3-Triazole-Containing Nitrones
dc.creator.none.fl_str_mv Hadjipavlou-Litina, Dimitra
Głowacka, Iwona E.
Marco-Contelles, José
Piotrowska, Dorota G.
author Hadjipavlou-Litina, Dimitra
author_facet Hadjipavlou-Litina, Dimitra
Głowacka, Iwona E.
Marco-Contelles, José
Piotrowska, Dorota G.
author_role author
author2 Głowacka, Iwona E.
Marco-Contelles, José
Piotrowska, Dorota G.
author2_role author
author
author
dc.contributor.none.fl_str_mv University of Lodz
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Antioxidants
oxidative stress
1,2,3-Triazole-containing nitrones
topic Antioxidants
oxidative stress
1,2,3-Triazole-containing nitrones
description Herein, we report the synthesis and antioxidant capacity of twelve novel 1,2,3-triazole-containing nitrones such as N-(2-(4-aryl-1H-1,2,3-triazol-1-yl)ethylidene)methanamine oxides 8a–f and N-(2-(4-aryl)-1H-1,2,3-triazol-1-yl)ethylidene)-2-methylpropan-2-amine oxides 9a–f, bearing an N-methyl, and an N-t-butyl substituent, respectively, at the nitrogen of the nitrone motif. Nitrones 8 and 9 were studied with regard to their antioxidant ability, as well as their ability to inhibit soybean lypoxygenase (LOX), and their in vitro antioxidant activity. For this, we used three different antioxidant assays, such as that featuring the interaction with the water-soluble azo compound AAPH for the inhibition of lipid peroxidation (LP), the competition with the DMSO for scavenging hydroxyl radicals, and the ABTS–decolorization assay. t-Butyl nitrone 9e, bearing the 2,4-difluorophenyl motif, showed a strong LP inhibitory effect (100%), close to the reference compound Trolox (93%), being the most potent LP inhibitor (LPi) of the whole series of tested nitrones. Nitrones 9d, 9e and 9f, bearing the 4-fluorophenyl, 2,4-difluorophenyl, and 4-fluoro-3-methylphenyl motif, respectively, were almost equipotent, and the most potent hydroxyl radical scavengers (~100%), more potent than Trolox (88%), were used as a reference compound. Regarding the LOX inhibition, the most potent inhibitor was the t-butyl substituted nitrone 9f (27 μM), bearing the 4-fluoro-3-methylphenyl motif, being 60-fold less potent than NDGA (0.45 μM), which was used as the standard in this test. The results from the antioxidant determination in the ABTS radical cation (ABTS) decolorization assay were not significant. N-Methyl nitrone 8f, bearing the 4-fluoro-3-methylphenyl motif, was the only promising representative, with a value of 34.3%, followed by nitrone 9f (16%). From the antioxidant analyses, we have identified N-(2-(4-(4-fluoro-3-methylphenyl)-1H-1,2,3-triazol-1-yl)ethylidene)-2-methylpropan-2-amine oxide (9f), bearing t-butyl and 4-fluoro-3-methylphenyl motifs in its structure, as the most balanced and potent antioxidant agent among the tested nitrones, as it was the most potent LOX inhibitor (27 μM), an extremely efficient and potent hydroxyl radical scavenger (99.9%), as well as one of the most potent LPi (87%) and ABTS scavengers (16%).
publishDate 2023
dc.date.none.fl_str_mv 2023
2023
2023
2023
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/306940
url http://hdl.handle.net/10261/306940
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv http://dx.doi.org/10.3390/antiox12010036
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute
publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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