Synthesis, cytotoxicity and anti-cancer activity of new alkynyl-gold(i) complexes

Abstract

Alkynyl(triphenylphosphine)gold(i) complexes carrying variously substituted propargylic amines have been synthesized and fully characterized in solution and solid state. High levels of toxicity (i.e. micromolar range) were recognized for a series of cancer cell lines with particular emphasis on HT29, IGROV1, HL60 and I407. In particular the lead compound 3ab was identified as the most active compound in all cell lines (IC50: 1.7-7.9 μM).

The anticancer effect related to disturbances in redox balance on Caco-2 cells caused by an alkynyl gold(I) complex

“…On the other hand, GSR lack of this a selenylsulfide/selenothiol motif and in consequence the access of drugs in general, and [Au(C CPh)(PTA)] in particular, to the active centre might be hamper, impeding drug inhibition. The inhibition of TrxR activity has been also found in different alkynyl gold(I) derivatives reported previously [89][90][91][92][93]. These results suggest a selectivity of gold alkynyl compounds towards TrxR over other related enzymes such as GSR, as it was previously described in the literature by Meyer et al [93].…”

Small molecule inhibitors of mammalian thioredoxin reductase as potential anticancer agents: An update

“…As shown in Table , complexes 108–110 showed IC 50 values more than two orders of magnitude higher than the control drug auranofin. In addition, complexes 111 and 112 displayed a strong inhibition of TrxR with submicromolar potency and remarkable cytotoxicity (Table ) . A cobaltoceniumethynyl gold (I) complex ( 113 , Figure C) was reported by Ott and co‐workers in 2016, which triggered efficient cytotoxic effects in tumor cells (Table ) and inhibited TrxR activity with an IC 50 value of 0.11 μM …”

Gold and platinum alkynyl complexes for biomedical applications

“…Coordination of the triphenylphosphane gold moiety to propargylic amine ligands (complexes 12-14, Fig. 3) led to a family of derivatives, 43 in which the presence of different substituents on the nitrogen atom modulates their overall cytotoxic properties. Therefore, the most effective in inhibiting cell growth in HT29 human colorectal carcinoma, IGROV1 human ovarian carcinoma and HL60 promyelocytic leukemia cell line, were both complexes 13a and 13d with para-substituted benzene sulfonamide unit.…”