Please use this identifier to cite or link to this item: https://www.arca.fiocruz.br/handle/icict/16565
Title: Molecular hybridization as a powerful tool towards multitarget quinoidal systems: synthesis, trypanocidal and antitumor activities of naphthoquinone-based 5-iodo-1,4-disubstituted-, 1,4- and 1,5-disubstituted-1,2,3-triazoles
Authors: Bahia, Samara Ben B. B
Reis, Wallace J.
Jardim, Guilherme A. M.
Souto, Francielly T.
Simone, Carlos A. de
Gatto, Claudia C.
Menna-Barreto, Ruben F. S.
Castro, Solange L. de
Cavalcanti, Bruno C.
Pessoa, Claudia
Araujo, Mara H.
Silva Júnior, Eufrânio N. da
Affilliation: Universidade Federal de Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.
Universidade Federal de MInas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.
Universidade Federal de MInas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.
Universidade Federal de MInas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.
Universidade de São Paulo. Instituto de Física. Departamento de Física e Informática. São Paulo, SP, Brasil.
Universidade de Brasília. Instituto de Química. Brasília, DF, Brasil.
Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Rio de Janeiro, RJ, Brasil.
Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Rio de Janeiro, RJ, Brasil.
Universidade Federal do Ceará. Departamento de Fisiologia e Farmacologia. Fortaleza, CE, Brasil.
Universidade Federal do Ceará. Departamento de Fisiologia e Farmacologia. Fortaleza, CE, Brasil.
Universidade Federal de Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.
Universidade Federal de Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.
Abstract: Quinonoid compounds based on 5-iodo-1,4-disubstituted-, 1,4- and 1,5-disubstituted-1,2,3-triazoles were synthesized using simple methodologies and evaluated against T. cruzi, the etiological agent of Chagas disease, and cancer cell lines PC3, HCT-116, HL-60, MDA-MB-435 and SF-295. The cytotoxic potential of the lapachones was also assayed against peripheral blood mononuclear cells (PBMC). Two compounds 6 and 12 were identified as potential hits against T. cruzi. β-Lapachone-based 1,5-disubstituted-1,2,3-triazole (12) displayed an IC50/24 h = 125.1 μM, similar to benznidazole, the standard drug. Compound 12 was also more active than the precursor β-lapachone against the cancer cell lines. These compounds acting as multitarget quinoidal systems could provide promising new leads for the development of trypanocidal and/ or anticancer drugs.
Keywords: Chagas Disease
T. cruzi
cancer cell lines
naphthoquinone
triazoles
keywords: Doença de Chagas
Trypanosoma cruzi
Linhas celulares de câncer
Naftoquinona
triazoles
Issue Date: 2016
Publisher: The Royal Society of Chemistry
Citation: BAHIA, Samara Ben B. B. et al. Molecular hybridization as a powerful tool towards multitarget quinoidal systems: synthesis, trypanocidal and antitumor activities of naphthoquinone-based 5-iodo-1,4-disubstituted-, 1,4- and 1,5-disubstituted-1,2,3-triazoles. Med. Chem. Commun., v.7, n.1555, 10p, 2016.
DOI: 10.1039/c6md00216a
ISSN: 2040-2503
Copyright: restricted access
Appears in Collections:IOC - Artigos de Periódicos

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