In Vitro and In Vivo Investigations into the Carbene Gold Chloride and Thioglucoside Anticancer Drug Candidates NHC-AuCl and NHC-AuSR

Evaluating Ligand Modifications of the Titanocene and Auranofin Moieties for the Development of More Potent Anticancer Drugs

“…Like AF, the two Au(I) compounds enhanced oxidative stress resulting in apoptotic cell death. The molecular modeling results suggested that the thioglucose analogue could be a potential ligand for glucose transporter 1 [111]. Recent efforts have tried to determine whether the thioglucose ligand may be able to facilitate a receptor mediated delivery of AF.…”

“…Like AF, the two Au(I) compounds enhanced oxidative stress resulting in apoptotic cell death. The molecular modeling results suggested that the thioglucose analogue could be a potential ligand for glucose transporter 1 [111]. To further study the role of the thioglucose ligand of the AF analogue, Dada et al studied the replacement of this ligand with other sugars that have been conjugated to anticancer drugs in order to take advantage of the GLUT-mediated cellular uptake, which could potentially lead to a heightened activity [110].…”

Novel derivatives of the antibiotic NHC–Ag(I) drug candidate SBC3: Synthesis, biological evaluation and 109Ag NMR studies

“…Lipophilic character of the stabilising NHC ligand has been shown to be a key characteristic in NHC-Au(I) anticancer compounds [14,21]. Previous research by our group has led to the hypothesis that lipophilic substituents are a large factor by which the antibiotic compound SBC3, a silver(I) complex containing four lipophilic phenyl rings ( Fig.…”

The non-isomorphous crystal structures of NHC—Au—Cl and NHC—Au—Br (NHC is 1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene)

“…These gold monohalides can be transformed into monomeric complexes by ligands such as CO, PPh 3 or Me 2 S; the resulting linear L-Au-Cl species show relatively short Au-Cl distances of 2.261 (6) Å for the CO complex (Jones, 1982), 2.279 (3) Å for the Ph 3 P complex (Baenziger et al, 1976) and 2.288 (2) Å for the Me 2 S complex (Jones & Lautner, 1988). Such ligand-stabilized gold monochloride compounds have been investigated as catalysts (Hashmi & Hutchings, 2006), luminescent materials (Mercs & Albrecht, 2010) and anticancer drugs (Ott, 2009), especially when coordinated to a lipophilic benzyl-substituted N-hetero- (Patil et al, 2011;Kaps et al, 2012;Hackenberg et al, 2013;Walther et al, 2016). Halide exchange is a known process for ligand-stabilized gold monohalide compounds (Sanagawa et al, 2013).…”