Synthesis and Biological Studies on Dinuclear Gold(I) Complexes with Di-(N-Heterocyclic Carbene) Ligands Functionalized with Carbohydrates

Abstract

The design of novel metal complexes with N-heterocyclic carbene (NHC) ligands that display biological activity is an active research field in organometallic chemistry. One of the possible approaches consists of the use of NHC ligands functionalized with a carbohydrate moiety. Two novel Au(I)–Au(I) dinuclear complexes were synthesized; they present a neutral structure with one bridging diNHC ligand, having one or both heterocyclic rings decorated with a carbohydrate functionality. With the symmetric diNHC ligand, the dicationic dinuclear complex bearing two bridging diNHC ligands was also synthesized. The study was completed by analyzing the antiproliferative properties of these complexes, which were compared to the activity displayed by similar mononuclear Au(I) complexes and by the analogous bimetallic Au(I)–Au(I) complex not functionalized with carbohydrates.

From Au11 to Au13: Tailored Synthesis of Superatomic Di-NHC/PPh3-Stabilized Molecular Gold Nanoclusters

“…Our group has a longstanding experience in the chemistry of dinuclear gold­(I) complexes with di-NHC ligands, − and we envisaged the possibility of exploiting them in an alternative way as reagents for the preparation of novel NHC-stabilized AuNCs (Scheme C). Our synthetic approach involves the use of these complexes, which are more stable and easily manipulated than free di-NHCs, for the chemical modification of preformed AuNCs.…”

Halo complexes of gold(i) containing glycoconjugate carbene ligands: synthesis, characterization, cytotoxicity and interaction with proteins and DNA model systems

“…The complexes displayed IC 50 values in the high micromolar range, lower than those obtained for the related glycoconjugated dinuclear Au( i ) complexes, thus demonstrating an increased cytotoxicity. 57 Some distinctions by changing the halide ligand could be observed. The chloro derivative Au1 exerted a cytotoxic effect on A431 cells, whereas no IC 50 value was reached on HaCaT cells, stating some selectivity of this complex towards cancer cells.…”

“…Recently, a series of analogous di-nuclear Au(I) carbene complexes were designed and studied for their anticancer properties. 57 To further investigate the properties of glycoconjugate anticancer Au(I) NHC complexes, new neutral halo complexes have been synthesized and fully characterized (Au1-Au3 in Scheme 1). The carbene ligand Im-Me is decorated with a glucoside fragment via a triazole linker, easily obtainable through a click chemistry reaction.…”

“…Recently, a series of analogous di-nuclear Au( i ) carbene complexes were designed and studied for their anticancer properties. 57…”

Carbohydrate-based N-heterocyclic carbene-metal complexes: a new avenue for sustainable catalysts in organic transformations

“…The incorporation of these physiologically active residues into the skeleton of NHC-metal complexes may reduce toxicity while increasing biocompatibility and solubility. 32 Carbohydrates have also been employed as key precursors in various other domains including chemoenzymatic reactions, anti-cancer agents, [33][34][35][36] antiproliferative activity, 37 and biobased ionic liquids. [38][39][40] An overview of numerous carbohydrate-based NHC-metal complexes is presented in Fig.…”