Electrochemical evidence of nitrate release from the nitrooxy compound 4-((nitrooxy) methyl)-3-nitrobenzoic acid and its antinociceptive and anti-inflammatory activities in mice

Alysson Vinícius Braga; Ivo Souza Ferraz Melo; Armando da Silva Cunha Júnior; Isabela da Costa César; Marília Oliveira Fonseca Goulart; Renata Barbosa de Oliveira; Márcio de Matos Coelho; Renes Resende Machado; Roger Ryuler Lisboa da Silva; Ianny Bandeira Rodrigues; Gabriel Vitor de Lima Marques; Andre Felippe de Almeida Xavier; Anastacio Boane; Mayara Rodrigues Brandão de Paiva; Pedro Henrique Cavalcanti Franco; Felipe Fernandes Rodrigues

Electrochemical evidence of nitrate release from the nitrooxy compound 4-((nitrooxy) methyl)-3-nitrobenzoic acid and its antinociceptive and anti-inflammatory activities in mice

Detalhes bibliográficos
Autor(a) principal:	Alysson Vinícius Braga
Data de Publicação:	2021
Outros Autores:	Ivo Souza Ferraz Melo, Armando da Silva Cunha Júnior, Isabela da Costa César, Marília Oliveira Fonseca Goulart, Renata Barbosa de Oliveira, Márcio de Matos Coelho, Renes Resende Machado, Roger Ryuler Lisboa da Silva, Ianny Bandeira Rodrigues, Gabriel Vitor de Lima Marques, Andre Felippe de Almeida Xavier, Anastacio Boane, Mayara Rodrigues Brandão de Paiva, Pedro Henrique Cavalcanti Franco, Felipe Fernandes Rodrigues
Tipo de documento:	Artigo
Idioma:	eng
Título da fonte:	Repositório Institucional da UFMG
Texto Completo:	https://doi.org/10.1016/j.biopha.2020.110913 http://hdl.handle.net/1843/56504 https://orcid.org/0000-0003-1349-9413
Resumo:	CNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico

Metadados do item

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spelling	2023-07-17T20:30:09Z2023-07-17T20:30:09Z2021-0113311091311https://doi.org/10.1016/j.biopha.2020.1109130753-3322http://hdl.handle.net/1843/56504https://orcid.org/0000-0003-1349-9413CNPq - Conselho Nacional de Desenvolvimento Científico e TecnológicoOutra AgênciaConsidering the many biological activities of nitric oxide (NO), some lines of research focused on the modulation of these activities through the provision of this mediator by designing and synthesizing compounds coupled with an NO donor group. Thus, the objectives of the present study were to carry out an electrochemical investigation of the nitrooxy compound 4-((nitrooxy) methyl)-3-nitrobenzoic acid (1) and evaluate its activities and putative mechanisms in experimental models of pain and inflammation. Voltammetric studies performed in aprotic medium (mimetic of membranes) showed important electrochemical reduction mechanisms: nitroaromatic reduction, self-protonation, and finally reductive elimination, which leads to nitrate release. Systemic admin istration of the nitrooxy compound (1) inhibited the nociceptive response induced by heat and the tactile hypersensitivity and paw edema induced by carrageenan in mice. The activities in the models of inflammatory pain and edema were associated with reduced neutrophil recruitment and production of inflammatory cytokines, such as interleukin (IL)-1β, IL-6, tumor necrosis factor-α and CXCL-1, and increased production of IL-10. Concluding, electrochemical analysis revealed unequivocally that electron transfer at the nitro group of the nitrooxy com pound (1) results in the cleavage of the organic nitrate, potentially resulting in the generation of NO. This electrochemical mechanism may be compared to a biochemical electron-transfer mediated nitrate release that, by appropriate in vivo bioreduction (enzymatic or not) would lead to NO production. Compound (1) exhibits activities in models of inflammatory pain and edema that may be due to reduced recruitment of neutrophils and production of inflammatory cytokines and increased production of IL-10. These results reinforce the interest in the investigation of NO donor compounds as candidates for analgesic and anti-inflammatory drugs.engUniversidade Federal de Minas GeraisUFMGBrasilFAR - DEPARTAMENTO DE PRODUTOS FARMACÊUTICOSFARMACIA - FACULDADE DE FARMACIAICX - DEPARTAMENTO DE QUÍMICABiomedicine & PharmacotherapyFarmáciaQuímicaFarmáciaQuímicaElectrochemical evidence of nitrate release from the nitrooxy compound 4-((nitrooxy) methyl)-3-nitrobenzoic acid and its antinociceptive and anti-inflammatory activities in miceinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttps://www.sciencedirect.com/science/article/pii/S0753332220311057?via%3DihubAlysson Vinícius BragaIvo Souza Ferraz MeloArmando da Silva Cunha JúniorIsabela da Costa CésarMarília Oliveira Fonseca GoulartRenata Barbosa de OliveiraMárcio de Matos CoelhoRenes Resende MachadoRoger Ryuler Lisboa da SilvaIanny Bandeira RodriguesGabriel Vitor de Lima MarquesAndre Felippe de Almeida XavierAnastacio BoaneMayara Rodrigues Brandão de PaivaPedro Henrique Cavalcanti FrancoFelipe Fernandes Rodriguesapplication/pdfinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFMGinstname:Universidade Federal de Minas Gerais (UFMG)instacron:UFMGLICENSELicense.txtLicense.txttext/plain; charset=utf-82042https://repositorio.ufmg.br/bitstream/1843/56504/1/License.txtfa505098d172de0bc8864fc1287ffe22MD51ORIGINALElectrochemical evidence of nitrate release from the nitrooxy compound 4-((nitrooxy) methyl)-3-nitrobenzoic acid and its antinociceptive and anti-inflammatory activities in mice.pdfElectrochemical evidence of nitrate release from the nitrooxy compound 4-((nitrooxy) methyl)-3-nitrobenzoic acid and its antinociceptive and anti-inflammatory activities in mice.pdfapplication/pdf40307340https://repositorio.ufmg.br/bitstream/1843/56504/2/Electrochemical%20evidence%20of%20nitrate%20release%20from%20the%20nitrooxy%20compound%204-%28%28nitrooxy%29%20methyl%29-3-nitrobenzoic%20acid%20and%20its%20antinociceptive%20and%20anti-inflammatory%20activities%20in%20mice.pdf85673c906f7c0162243199831ae5d5c2MD521843/565042023-07-17 17:30:10.02oai:repositorio.ufmg.br:1843/56504TElDRU7vv71BIERFIERJU1RSSUJVSe+/ve+/vU8gTu+/vU8tRVhDTFVTSVZBIERPIFJFUE9TSVTvv71SSU8gSU5TVElUVUNJT05BTCBEQSBVRk1HCiAKCkNvbSBhIGFwcmVzZW50Ye+/ve+/vW8gZGVzdGEgbGljZW7vv71hLCB2b2Pvv70gKG8gYXV0b3IgKGVzKSBvdSBvIHRpdHVsYXIgZG9zIGRpcmVpdG9zIGRlIGF1dG9yKSBjb25jZWRlIGFvIFJlcG9zaXTvv71yaW8gSW5zdGl0dWNpb25hbCBkYSBVRk1HIChSSS1VRk1HKSBvIGRpcmVpdG8gbu+/vW8gZXhjbHVzaXZvIGUgaXJyZXZvZ++/vXZlbCBkZSByZXByb2R1emlyIGUvb3UgZGlzdHJpYnVpciBhIHN1YSBwdWJsaWNh77+977+9byAoaW5jbHVpbmRvIG8gcmVzdW1vKSBwb3IgdG9kbyBvIG11bmRvIG5vIGZvcm1hdG8gaW1wcmVzc28gZSBlbGV0cu+/vW5pY28gZSBlbSBxdWFscXVlciBtZWlvLCBpbmNsdWluZG8gb3MgZm9ybWF0b3Mg77+9dWRpbyBvdSB277+9ZGVvLgoKVm9j77+9IGRlY2xhcmEgcXVlIGNvbmhlY2UgYSBwb2zvv710aWNhIGRlIGNvcHlyaWdodCBkYSBlZGl0b3JhIGRvIHNldSBkb2N1bWVudG8gZSBxdWUgY29uaGVjZSBlIGFjZWl0YSBhcyBEaXJldHJpemVzIGRvIFJJLVVGTUcuCgpWb2Pvv70gY29uY29yZGEgcXVlIG8gUmVwb3NpdO+/vXJpbyBJbnN0aXR1Y2lvbmFsIGRhIFVGTUcgcG9kZSwgc2VtIGFsdGVyYXIgbyBjb250Ze+/vWRvLCB0cmFuc3BvciBhIHN1YSBwdWJsaWNh77+977+9byBwYXJhIHF1YWxxdWVyIG1laW8gb3UgZm9ybWF0byBwYXJhIGZpbnMgZGUgcHJlc2VydmHvv73vv71vLgoKVm9j77+9IHRhbWLvv71tIGNvbmNvcmRhIHF1ZSBvIFJlcG9zaXTvv71yaW8gSW5zdGl0dWNpb25hbCBkYSBVRk1HIHBvZGUgbWFudGVyIG1haXMgZGUgdW1hIGPvv71waWEgZGUgc3VhIHB1YmxpY2Hvv73vv71vIHBhcmEgZmlucyBkZSBzZWd1cmFu77+9YSwgYmFjay11cCBlIHByZXNlcnZh77+977+9by4KClZvY++/vSBkZWNsYXJhIHF1ZSBhIHN1YSBwdWJsaWNh77+977+9byDvv70gb3JpZ2luYWwgZSBxdWUgdm9j77+9IHRlbSBvIHBvZGVyIGRlIGNvbmNlZGVyIG9zIGRpcmVpdG9zIGNvbnRpZG9zIG5lc3RhIGxpY2Vu77+9YS4gVm9j77+9IHRhbWLvv71tIGRlY2xhcmEgcXVlIG8gZGVw77+9c2l0byBkZSBzdWEgcHVibGljYe+/ve+/vW8gbu+/vW8sIHF1ZSBzZWphIGRlIHNldSBjb25oZWNpbWVudG8sIGluZnJpbmdlIGRpcmVpdG9zIGF1dG9yYWlzIGRlIG5pbmd177+9bS4KCkNhc28gYSBzdWEgcHVibGljYe+/ve+/vW8gY29udGVuaGEgbWF0ZXJpYWwgcXVlIHZvY++/vSBu77+9byBwb3NzdWkgYSB0aXR1bGFyaWRhZGUgZG9zIGRpcmVpdG9zIGF1dG9yYWlzLCB2b2Pvv70gZGVjbGFyYSBxdWUgb2J0ZXZlIGEgcGVybWlzc++/vW8gaXJyZXN0cml0YSBkbyBkZXRlbnRvciBkb3MgZGlyZWl0b3MgYXV0b3JhaXMgcGFyYSBjb25jZWRlciBhbyBSZXBvc2l077+9cmlvIEluc3RpdHVjaW9uYWwgZGEgVUZNRyBvcyBkaXJlaXRvcyBhcHJlc2VudGFkb3MgbmVzdGEgbGljZW7vv71hLCBlIHF1ZSBlc3NlIG1hdGVyaWFsIGRlIHByb3ByaWVkYWRlIGRlIHRlcmNlaXJvcyBlc3Tvv70gY2xhcmFtZW50ZSBpZGVudGlmaWNhZG8gZSByZWNvbmhlY2lkbyBubyB0ZXh0byBvdSBubyBjb250Ze+/vWRvIGRhIHB1YmxpY2Hvv73vv71vIG9yYSBkZXBvc2l0YWRhLgoKQ0FTTyBBIFBVQkxJQ0Hvv73vv71PIE9SQSBERVBPU0lUQURBIFRFTkhBIFNJRE8gUkVTVUxUQURPIERFIFVNIFBBVFJPQ++/vU5JTyBPVSBBUE9JTyBERSBVTUEgQUfvv71OQ0lBIERFIEZPTUVOVE8gT1UgT1VUUk8gT1JHQU5JU01PLCBWT0Pvv70gREVDTEFSQSBRVUUgUkVTUEVJVE9VIFRPRE9TIEUgUVVBSVNRVUVSIERJUkVJVE9TIERFIFJFVklT77+9TyBDT01PIFRBTULvv71NIEFTIERFTUFJUyBPQlJJR0Hvv73vv71FUyBFWElHSURBUyBQT1IgQ09OVFJBVE8gT1UgQUNPUkRPLgoKTyBSZXBvc2l077+9cmlvIEluc3RpdHVjaW9uYWwgZGEgVUZNRyBzZSBjb21wcm9tZXRlIGEgaWRlbnRpZmljYXIgY2xhcmFtZW50ZSBvIHNldSBub21lKHMpIG91IG8ocykgbm9tZXMocykgZG8ocykgZGV0ZW50b3IoZXMpIGRvcyBkaXJlaXRvcyBhdXRvcmFpcyBkYSBwdWJsaWNh77+977+9bywgZSBu77+9byBmYXLvv70gcXVhbHF1ZXIgYWx0ZXJh77+977+9bywgYWzvv71tIGRhcXVlbGFzIGNvbmNlZGlkYXMgcG9yIGVzdGEgbGljZW7vv71hLgo=Repositório de PublicaçõesPUBhttps://repositorio.ufmg.br/oaiopendoar:2023-07-17T20:30:10Repositório Institucional da UFMG - Universidade Federal de Minas Gerais (UFMG)false
dc.title.pt_BR.fl_str_mv	Electrochemical evidence of nitrate release from the nitrooxy compound 4-((nitrooxy) methyl)-3-nitrobenzoic acid and its antinociceptive and anti-inflammatory activities in mice
title	Electrochemical evidence of nitrate release from the nitrooxy compound 4-((nitrooxy) methyl)-3-nitrobenzoic acid and its antinociceptive and anti-inflammatory activities in mice
spellingShingle	Electrochemical evidence of nitrate release from the nitrooxy compound 4-((nitrooxy) methyl)-3-nitrobenzoic acid and its antinociceptive and anti-inflammatory activities in mice Alysson Vinícius Braga Farmácia Química Farmácia Química
title_short	Electrochemical evidence of nitrate release from the nitrooxy compound 4-((nitrooxy) methyl)-3-nitrobenzoic acid and its antinociceptive and anti-inflammatory activities in mice
title_full	Electrochemical evidence of nitrate release from the nitrooxy compound 4-((nitrooxy) methyl)-3-nitrobenzoic acid and its antinociceptive and anti-inflammatory activities in mice
title_fullStr	Electrochemical evidence of nitrate release from the nitrooxy compound 4-((nitrooxy) methyl)-3-nitrobenzoic acid and its antinociceptive and anti-inflammatory activities in mice
title_full_unstemmed	Electrochemical evidence of nitrate release from the nitrooxy compound 4-((nitrooxy) methyl)-3-nitrobenzoic acid and its antinociceptive and anti-inflammatory activities in mice
title_sort	Electrochemical evidence of nitrate release from the nitrooxy compound 4-((nitrooxy) methyl)-3-nitrobenzoic acid and its antinociceptive and anti-inflammatory activities in mice
author	Alysson Vinícius Braga
author_facet	Alysson Vinícius Braga Ivo Souza Ferraz Melo Armando da Silva Cunha Júnior Isabela da Costa César Marília Oliveira Fonseca Goulart Renata Barbosa de Oliveira Márcio de Matos Coelho Renes Resende Machado Roger Ryuler Lisboa da Silva Ianny Bandeira Rodrigues Gabriel Vitor de Lima Marques Andre Felippe de Almeida Xavier Anastacio Boane Mayara Rodrigues Brandão de Paiva Pedro Henrique Cavalcanti Franco Felipe Fernandes Rodrigues
author_role	author
author2	Ivo Souza Ferraz Melo Armando da Silva Cunha Júnior Isabela da Costa César Marília Oliveira Fonseca Goulart Renata Barbosa de Oliveira Márcio de Matos Coelho Renes Resende Machado Roger Ryuler Lisboa da Silva Ianny Bandeira Rodrigues Gabriel Vitor de Lima Marques Andre Felippe de Almeida Xavier Anastacio Boane Mayara Rodrigues Brandão de Paiva Pedro Henrique Cavalcanti Franco Felipe Fernandes Rodrigues
author2_role	author author author author author author author author author author author author author author author
dc.contributor.author.fl_str_mv	Alysson Vinícius Braga Ivo Souza Ferraz Melo Armando da Silva Cunha Júnior Isabela da Costa César Marília Oliveira Fonseca Goulart Renata Barbosa de Oliveira Márcio de Matos Coelho Renes Resende Machado Roger Ryuler Lisboa da Silva Ianny Bandeira Rodrigues Gabriel Vitor de Lima Marques Andre Felippe de Almeida Xavier Anastacio Boane Mayara Rodrigues Brandão de Paiva Pedro Henrique Cavalcanti Franco Felipe Fernandes Rodrigues
dc.subject.por.fl_str_mv	Farmácia Química
topic	Farmácia Química Farmácia Química
dc.subject.other.pt_BR.fl_str_mv	Farmácia Química
description	CNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
publishDate	2021
dc.date.issued.fl_str_mv	2021-01
dc.date.accessioned.fl_str_mv	2023-07-17T20:30:09Z
dc.date.available.fl_str_mv	2023-07-17T20:30:09Z
dc.type.status.fl_str_mv	info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv	info:eu-repo/semantics/article
format	article
status_str	publishedVersion
dc.identifier.uri.fl_str_mv	http://hdl.handle.net/1843/56504
dc.identifier.doi.pt_BR.fl_str_mv	https://doi.org/10.1016/j.biopha.2020.110913
dc.identifier.issn.pt_BR.fl_str_mv	0753-3322
dc.identifier.orcid.pt_BR.fl_str_mv	https://orcid.org/0000-0003-1349-9413
url	https://doi.org/10.1016/j.biopha.2020.110913 http://hdl.handle.net/1843/56504 https://orcid.org/0000-0003-1349-9413
identifier_str_mv	0753-3322
dc.language.iso.fl_str_mv	eng
language	eng
dc.relation.ispartof.pt_BR.fl_str_mv	Biomedicine & Pharmacotherapy
dc.rights.driver.fl_str_mv	info:eu-repo/semantics/openAccess
eu_rights_str_mv	openAccess
dc.format.none.fl_str_mv	application/pdf
dc.publisher.none.fl_str_mv	Universidade Federal de Minas Gerais
dc.publisher.initials.fl_str_mv	UFMG
dc.publisher.country.fl_str_mv	Brasil
dc.publisher.department.fl_str_mv	FAR - DEPARTAMENTO DE PRODUTOS FARMACÊUTICOS FARMACIA - FACULDADE DE FARMACIA ICX - DEPARTAMENTO DE QUÍMICA
publisher.none.fl_str_mv	Universidade Federal de Minas Gerais
dc.source.none.fl_str_mv	reponame:Repositório Institucional da UFMG instname:Universidade Federal de Minas Gerais (UFMG) instacron:UFMG
instname_str	Universidade Federal de Minas Gerais (UFMG)
instacron_str	UFMG
institution	UFMG
reponame_str	Repositório Institucional da UFMG
collection	Repositório Institucional da UFMG
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Electrochemical evidence of nitrate release from the nitrooxy compound 4-((nitrooxy) methyl)-3-nitrobenzoic acid and its antinociceptive and anti-inflammatory activities in mice

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