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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dc.creatorAlysson Vinícius Braga
dc.creatorIvo Souza Ferraz Melo
dc.creatorArmando da Silva Cunha Júnior
dc.creatorIsabela da Costa César
dc.creatorMarília Oliveira Fonseca Goulart
dc.creatorRenata Barbosa de Oliveira
dc.creatorMárcio de Matos Coelho
dc.creatorRenes Resende Machado
dc.creatorRoger Ryuler Lisboa da Silva
dc.creatorIanny Bandeira Rodrigues
dc.creatorGabriel Vitor de Lima Marques
dc.creatorAndre Felippe de Almeida Xavier
dc.creatorAnastacio Boane
dc.creatorMayara Rodrigues Brandão de Paiva
dc.creatorPedro Henrique Cavalcanti Franco
dc.creatorFelipe Fernandes Rodrigues
dc.date.accessioned2023-07-17T20:30:09Z
dc.date.accessioned2025-09-08T22:57:43Z
dc.date.available2023-07-17T20:30:09Z
dc.date.issued2021-01
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipOutra Agência
dc.format.mimetypepdf
dc.identifier.doihttps://doi.org/10.1016/j.biopha.2020.110913
dc.identifier.issn0753-3322
dc.identifier.urihttps://hdl.handle.net/1843/56504
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofBiomedicine & Pharmacotherapy
dc.rightsAcesso Aberto
dc.subjectFarmácia
dc.subjectQuímica
dc.subject.otherFarmácia
dc.subject.otherQuímica
dc.titleElectrochemical evidence of nitrate release from the nitrooxy compound 4-((nitrooxy) methyl)-3-nitrobenzoic acid and its antinociceptive and anti-inflammatory activities in mice
dc.typeArtigo de periódico
local.citation.epage11
local.citation.spage110913
local.citation.volume133
local.description.resumoConsidering 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.
local.identifier.orcidhttps://orcid.org/0000-0003-1349-9413
local.publisher.countryBrasil
local.publisher.departmentFAR - DEPARTAMENTO DE PRODUTOS FARMACÊUTICOS
local.publisher.departmentFARMACIA - FACULDADE DE FARMACIA
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://www.sciencedirect.com/science/article/pii/S0753332220311057?via%3Dihub

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