Please use this identifier to cite or link to this item: https://www.arca.fiocruz.br/handle/icict/27167
Title: Novel gold(I) complexes with 5-phenyl-1,3,4-oxadiazole-2-thione and phosphine as potential anticancer and antileishmanial agents
Authors: Chaves, Joana Darc Souza
Tunes, Luiza Guimaraes
Franco, Chris Hebert de Jesus
Martins, Thiago
Correa, Charlane Cimini
Murta, Silvane Maria Fonseca
Monte Neto, Rubens Lima
Silva, Heveline
Fontes, Ana Paula Soares
Almeida, Mauro Vieira de
Affilliation: Universidade Federal de Juiz de Fora. Instituto de Ciências Exatas. Departamento de Química. Juiz de Fora, MG, Brazil
Fundaçao Oswaldo Cruz. Instituto Rene Rachou. Belo Horizonte, MG, Brazil
Universidade Federal de Juiz de Fora. Instituto de Ciências Exatas. Departamento de Química. Juiz de Fora, MG, Brazil
Universidade Federal de Minas Gerais. Departamento de Física. Belo Horizonte, MG, Brazil
Universidade Federal de Juiz de Fora. Instituto de Ciências Exatas. Departamento de Química. Juiz de Fora, MG, Brazil
Fundaçao Oswaldo Cruz. Instituto Rene Rachou. Belo Horizonte, MG, Brazil
Fundaçao Oswaldo Cruz. Instituto Rene Rachou. Belo Horizonte, MG, Brazil
Universidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, Brazil
Universidade Federal de Juiz de Fora. Instituto de Ciências Exatas. Departamento de Química. Juiz de Fora, MG, Brazil
Universidade Federal de Juiz de Fora. Instituto de Ciências Exatas. Departamento de Química. Juiz de Fora, MG, Brazil
Abstract: The current anticancer and antileishmanial drug arsenal presents several limitations concerning their specificity, efficacy, costs and the emergence of drug-resistant cells lines, which encourages the urgent need to search for new alternatives. Inspired by the fact that gold(I)-based compounds are promising antitumoral and antileishmanial drug candidates, we synthesized novel gold(I) complexes containing phosphine and 5-phenyl-1,3,4-oxadiazole-2-thione and evaluated their anticancer and antileishmanial activities. Synthesis was performed by reacting 5-phenyl-1,3,4-oxadiazole-2-thione derivatives with chloro(triphenylphosphine)gold(I) and chloro(triethylphosphine)gold(I). The novel compounds were characterized by infrared, Raman, 1H, 13C nuclear magnetic resonance, high-resolution mass spectra, and x-ray crystallography. The coordination of the ligands to gold(I) occurred through the exocyclic sulfur atom. All gold(I) complexes were active at low micromolar or nanomolar range with IC50 values ranging from <0.10 to 1.66 mM against cancer cell lines and from 0.9 to 4.2 mM for Leishmania infantum intra-cellular amastigotes. Compound (6-A) was very selective against murine melanoma B16F10, colon cancer CT26.WT cell lines and L. infantum intracellular amastigotes. Compound (7-B) presented the highest anticancer activity against both cancer cell lines while the promising antileishmanial lead was compound (6-A). Tiethylphosphine gold(I) complexes were more active than the conterparts triphenylphosphine derivatives for both anticancer and antileishmanial activities. Triethylphosphine gold(I) derivatives presented antimony cross-resistance in L. guyanensis demonstrating their potential to be used as chemical tools to better understand mechanisms of drug resistance and action. These findings revealed the anticancer and antileishmanial potential of gold(I) oxadiazole phosphine derivatives.
Keywords: Gold(I) complexes
5-Phenyl-1,3,4-oxadiazole-2-thione
Antitumor activity
Antileishmania
keywords: Complexos de ouro (I)
5-Phenyl-1,3,4-oxadiazole-2-thione
Antitumor activity
antileishmanicidas
Issue Date: 2017
Publisher: Elsevier Masson SAS
Citation: CHAVES, Joana Darc Souza et al. Novel gold(I) complexes with 5-phenyl-1,3,4-oxadiazole-2-thione and phosphine as potential anticancer and antileishmanial agents. European Journal of Medicinal Chemistry, v. 127, p. 727-739, 2017
DOI: 10.1016/j.ejmech.2016.10.052
ISSN: 0223-5234
Copyright: restricted access
Appears in Collections:MG - IRR - Artigos de Periódicos

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