Synthesis of 1,2,3-triazole-containing methoxylated cinnamides and their antileishmanial activity against the leishmania braziliensis species

Página do item simplificado
dc.creatorFabíola Suelen dos Santos
dc.creatorRossimiriam Pereira de Freitas
dc.creatorCamila Simões de Freitas
dc.creatorDébora Vasconcelos Costa Mendonça
dc.creatorDaniela Pagliara Lage
dc.creatorGrasiele de Sousa Vieira Tavares
dc.creatorAmanda Sanchez Machado
dc.creatorVivian Tamieti Martins
dc.creatorAdilson Vidal Costa
dc.creatorVagner Tebaldi de Queiroz
dc.creatorMariana Belizario de Oliveira
dc.creatorFabrício Marques de Oliveira
dc.creatorLuciana Maria Ribeiro Antinarelli
dc.creatorElaine Soares Coimbra
dc.creatorEduardo Jorge Pilau
dc.creatorGeovane Perez da Silva
dc.creatorEduardo Antonio Ferraz Coelho
dc.creatorRóbson Ricardo Teixeira
dc.date.accessioned2025-02-12T21:28:47Z
dc.date.accessioned2025-09-09T00:27:15Z
dc.date.available2025-02-12T21:28:47Z
dc.date.issued2023-08-07
dc.format.mimetypepdf
dc.identifier.doihttps://doi.org/10.3390/ph16081113
dc.identifier.issn1424-8247
dc.identifier.urihttps://hdl.handle.net/1843/80006
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofPharmaceuticals
dc.rightsAcesso Aberto
dc.subjectLeishmania braziliensis
dc.subjectLeishmaniose
dc.subjectReações químicas
dc.subject.otherTegumentary leishmaniasis
dc.subject.otherLeishmania braziliensis
dc.subject.otherClick chemistry
dc.subject.otherCinnamic acid derivatives
dc.subject.otherCuAAC
dc.titleSynthesis of 1,2,3-triazole-containing methoxylated cinnamides and their antileishmanial activity against the leishmania braziliensis species
dc.typeArtigo de periódico
local.citation.epage20
local.citation.issue8
local.citation.spage1
local.citation.volume16
local.description.resumoLeishmaniasis is a group of infectious diseases caused by protozoan parasites that belong to the genus Leishmania. Currently, there is no human vaccine, and the available treatments are associated with toxicity, high cost, and the emergence of resistant strains. These factors highlight the need to identify new antileishmanial candidates. In this study, we synthesized twenty-four methoxylated cinnamides containing 1,2,3-triazole fragments and evaluated their antileishmanial activity against the Leishmania braziliensis species, which is the main etiological agent responsible for American Tegumentary Leishmaniasis (ATL). The cinnamides were synthetically prepared using nucleophilic acyl substitution and copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) reactions. The compounds were characterized using infrared, nuclear magnetic resonance, and high-resolution mass spectrometry techniques. We performed preliminary studies to evaluate the biological activity of these compounds against L. braziliensis promastigotes and axenic amastigotes. Compound 28, N-((1-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-1H-1,2,3-triazole-4-yl) methyl)-3,4-dimethoxy cinnamide, demonstrated relevant antileishmanial activity with low toxicity in murine cells. The selectivity index values for this compound were superior compared with data obtained using amphotericin B. Furthermore, this cinnamide derivative reduced the infection percentage and number of recovered amastigotes in L. braziliensis-infected macrophages. It also induced an increase in reactive oxygen species production, depolarization of the mitochondrial potential, and disruption of the parasite membrane. Taken together, these findings suggest that this synthetic compound holds potential as an antileishmanial candidate and should be considered for future studies in the treatment of ATL.
local.identifier.orcidhttps://orcid.org/0000-0001-6974-3724
local.identifier.orcidhttps://orcid.org/0000-0001-7882-215X
local.identifier.orcidhttps://orcid.org/0000-0001-7628-1871
local.identifier.orcidhttps://orcid.org/0000-0002-8710-9265
local.identifier.orcidhttps://orcid.org/0000-0001-5055-4915
local.identifier.orcidhttps://orcid.org/0000-0002-7968-8586
local.identifier.orcidhttps://orcid.org/0000-0002-8170-125X
local.identifier.orcidhttps://orcid.org/0000-0002-5341-2151
local.identifier.orcidhttps://orcid.org/0000-0002-6379-3840
local.identifier.orcidhttps://orcid.org/0000-0002-5183-1141
local.identifier.orcidhttps://orcid.org/0000-0003-1005-278X
local.identifier.orcidhttps://orcid.org/0000-0002-9175-3520
local.identifier.orcidhttps://orcid.org/0009-0001-5700-4251
local.identifier.orcidhttps://orcid.org/0000-0002-6681-9014
local.identifier.orcidhttps://orcid.org/0000-0003-3181-1108
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://www.mdpi.com/1424-8247/16/8/1113

Arquivos

Pacote original

Agora exibindo 1 - 1 de 1
Imagem de Miniatura
Nome:
Synthesis of 1,2,3-triazole-containing methoxylated cinnamides and their antileishmanial activity against the leishmania braziliensis species.pdf
Tamanho:
10.82 MB
Formato:
Adobe Portable Document Format
Baixar

Licença do pacote

Agora exibindo 1 - 1 de 1
Imagem de Miniatura
Nome:
License.txt
Tamanho:
1.99 KB
Formato:
Plain Text
Descrição:
Baixar

Coleções

Artigo de Periódico

Logo UFMG