Novel gold(I) complexes with 5-phenyl-1,3,4-oxadiazole-2-thione and phosphine as potential anticancer and antileishmanial agents

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 p...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2017-02, Vol.127, p.727-739
Main Authors: Chaves, Joana Darc S., Tunes, Luiza Guimarães, de J. Franco, Chris Hebert, Francisco, Thiago Martins, Corrêa, Charlane Cimini, Murta, Silvane M.F., Monte-Neto, Rubens Lima, Silva, Heveline, Fontes, Ana Paula S., de Almeida, Mauro V.
Format: Article
Language:English
Subjects:
5-Phenyl-1,3,4-oxadiazole-2-thione
Antileishmania
Antimony - pharmacology
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antiprotozoal Agents - chemistry
Antiprotozoal Agents - pharmacology
Antitumor activity
Cell Line, Tumor
Drug Design
Drug Resistance - drug effects
Gold - chemistry
Gold(I) complexes
Humans
Leishmania infantum - drug effects
Organogold Compounds - chemistry
Organogold Compounds - pharmacology
Oxadiazoles - chemistry
Phosphines - chemistry
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Summary: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
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2016.10.052