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.
Highlights
Cisplatin was used as an anticancer drug for many years, and it is still one of the most used ones, despite its numerous issues with drug resistance and side effects [1,2]
As Auranofin presents a phosphine ligand, it is reasonable to assume that this ligand could be substituted with an N-heterocyclic carbene (NHC) ligand, as NHCs are rapidly substituting phosphine ligands given the higher stability of the resulting complexes; as for phosphine ligands, for NHC ones it Molecules 2020, 25, 3850; doi:10.3390/molecules25173850
We report on the synthesis of dinuclear Au(I)–NHC complexes with incorporated acetylated glucopyranose moieties and on their antiproliferative activity
Summary
Cisplatin was used as an anticancer drug for many years, and it is still one of the most used ones, despite its numerous issues with drug resistance and side effects [1,2] These issues require more research to find a valid transition metal-based alternative to cisplatin. In this regard, metal complexes with N-heterocyclic carbene ligands (NHC) [3,4,5] are attracting increasing attention from the bioinorganic scientific community; these complexes are especially interesting due to their high stability imparted by the strength of the M–NHC bond, such that it appears reasonable that the structure of these complexes remains unchanged and stable under physiological conditions [6,7,8,9,10,11,12]. As Auranofin presents a phosphine ligand, it is reasonable to assume that this ligand could be substituted with an NHC ligand, as NHCs are rapidly substituting phosphine ligands given the higher stability of the resulting complexes; as for phosphine ligands, for NHC ones it Molecules 2020, 25, 3850; doi:10.3390/molecules25173850 www.mdpi.com/journal/molecules
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