Gold(i) complex of N,N′-disubstituted cyclic thiourea with in vitro and in vivo anticancer properties—potent tight-binding inhibition of thioredoxin reductase

Abstract

Coinage metal complexes of an N,N'-disubstituted cyclic thiourea exert significant cytotoxicities to cancer cells and, in particular, the gold(i) thiourea complex exhibits a potent tight-binding inhibition of the anticancer drug target thioredoxin reductase with an inhibitory constant at nanomolar level.

Synthesis and reactivity of N,N′-1,4-diazabutadiene derived borocations

“…12 As reported, it was shown that increasing steric bulk in the ortho position of the aniline led to more challenging reaction conditions. 1f required heating at reflux for 3 days, and was isolated in a low yield (23%), and 1h could not be formed even after 1 week heating at reflux.…”

Recent Advances in Gold(I) Complexes Based Biological Applications

“…Che et al have shown that bis-thiolate derived Au(I) complexes can be attained through the use of thiourea (TU) [24]. …”

Gold amides as anticancer drugs: synthesis and activity studies

“…The precursor ligands featured in complexes 1 and 2 were obtained after esterification of the corresponding amino acids 7 and 8 to their α-amino esters 11 followed by triflation of the primary amine with triflic anhydride ( Fig. 2).…”

“…The L-ligands can be phosphines, N-heterocyclic carbenes (NHCs) or sulfides, whereas the X-ligands range from thiolates, featured notably in the anti-rheumatoid auranofin, bis-triflic amide, chlorides, alkoxides, sulfonates and NHCs. [5][6][7][8][9][10][11][12][13] Previously the structural nature of ligands L and X limited their potential for derivatization and the corresponding complexes exhibited significant cytotoxicity. We have developed two complementary approaches that combine biocompatible ligands with tunable lipophilic groups to provide a platform for anti-cancer drug discovery.…”