Abstract
N-Heterocyclic carbene gold(I) complexes derived from 1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene (NHC*) represent a promising class of anticancer drugs. Complexes of the type NHC*-Au-L (L = Br−, I−, C≡C-R) and [NHC*-Au-L]+ (L = NHC*, PPh3) have been synthesised. The X-ray crystal structures of all gold(I) complexes are presented; aurophilic interactions were observed in five of the complexes. The anticancer activity was assessed via MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide)-based proliferation assays against the human colon carcinoma cell line HCT-116wt and the multidrug-resistant human breast carcinoma cell line MCF-7topo. Most complexes showed good cytotoxicity with IC50 values in the low micromolar range, while excellent sub-micromolar activity was observed for 2c, 3a and 3b. Generally, the activity of the ligands studied was as follows: carbene > phosphine > alkyne > halide, with an exception for the highly active iodido derivative 2c.
Highlights
IntroductionN-heterocyclic carbenes (NHCs) are desirable due to their high stability, versatility and lipophilicity [3]
In recent years, N-heterocyclic carbenes (NHCs) have been at the forefront of anticancer drug development [1,2].NHCs are desirable due to their high stability, versatility and lipophilicity [3]
They have demonstrated cytotoxic properties [4,5]. This is unsurprising as they are structurally analogous to the natural product Lepidiline A (Figure 1), a biologically active alkaloid isolated from Lepidium meyenii, the Peruvian maca root [6]
Summary
NHCs are desirable due to their high stability, versatility and lipophilicity [3]. They have demonstrated cytotoxic properties [4,5]. This is unsurprising as they are structurally analogous to the natural product Lepidiline A (Figure 1), a biologically active alkaloid isolated from Lepidium meyenii, the Peruvian maca root [6]. The structure of Lepidiline A (1,3-dibenzyl-4,5-dimethylimidazolium chloride) has been adapted to afford. 1,3-dibenzyl-4,5-diphenylimidazolium bromide (Figure 1, 1), the ancillary ligand present in the series of gold(I) complexes in this work. The refinement of NHCs has resulted in many cytotoxic
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