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Gold(I) Complexes with a Quinazoline Carboxamide Alkynyl Ligand: Synthesis, Cytotoxicity, and Mechanistic Studies. | LitMetric
A series of gold(I) complexes with the general formula [Au()()] (=4-phenyl--(prop-2-yn-1-yl)quinazoline-2-carboxamide, =PPh (triphenylphosphine), ; TPA (1,3,5-triaza-7-phosphaadamantane), , and Me-imy (1,3-dimethylimidazol-2-ylidene), ) were synthesized and fully characterized by spectroscopic methods. The alkynyl ligand belongs to the quinazoline carboxamide class of ligands that are known to bind to the translocator protein (TSPO) at the outer mitochondrial membrane. and exert cytotoxic effects in bladder cancer cells with IC values in the low micromolar range. Further mechanistic analysis indicated that the two complexes both act by inducing reactive oxygen species and caspase-mediated apoptosis. The complexes inhibit thioredoxin reductase, an established target of anticancer gold(I) complexes. Docking studies confirmed that after ligand exchange the free ligand can interact with the TSPO binding site.
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