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In this paper we describe the synthesis of new <i>N</i>-heterocyclic carbene (NHC) gold(I) derivatives with flavone-derived ligands with a propargyl ether group. The compounds were screened for their antimicrobial and anticancer activities, showing greater activity against bacteria than against colon cancer cells (Caco-2). Complexes [Au(L2b)(IMe)] (<b>1b</b>) and [Au(L2b)(IPr)] (<b>2b</b>) were found to be active against both Gram-positive and Gram-negative strains. The mechanism of action of <b>1b</b> was evaluated by measurement of thioredoxin reductase (TrxR) and dihydrofolate reductase (DHFR) activity, besides scanning electron microscopy (SEM). Inhibition of the enzyme thioredoxin reductase is not observed in either <i>Escherichia Coli</i> or Caco-2 cells; however, DHFR activity is compromised after incubation of <i>E. coli</i> cells with complex <b>1b</b>. Moreover, loss of structural integrity and change in bacterial shape is observed in the images obtained from scanning electron microscopy (SEM) after treatment <i>E. coli</i> cells with complex <b>1b</b>.