Homochiral imidazolium-based dicarboxylate silver(i) compounds: synthesis, characterisation and antimicrobial properties

Abstract

Complexes [Ag(LR)], 2 (LR = 2,2'-(imidazolium-1,3-diyl)di(2-alkylacetate)), were prepared by treatment of compounds HLR, 1, with Ag2O. They were characterised by analytical, spectroscopic (IR, 1H and 13C NMR and polarimetry) and...

Chirality influence on the cytotoxic properties of anionic chiral bis(N-heterocyclic carbene)silver complexes

“…These data suggest a chiralityanticancer correlation. An analogous tendency was recently observed by us in the antimicrobial study of amino acid based carboxylate silver complexes, where a slight different behavior was observed for enantiomerically related complexes [37].…”

“…Initially, we planned the synthesis of bis(carbene) silver complexes 2 by reaction of compounds HL R (1, 2-(1-(carboxyalkyl)-1H-imidazol-3ium-3-yl)carboxylate) with Ag 2 O in methanol. Surprisingly, dicarboxylate silver compounds, [Ag(L R )], were instead obtained, which were characterized as coordination polymeric species in the solid-state [37]. In solution, the C 2 -H group of imidazolium in [Ag(L R )] complexes experienced a fast H -D exchange with D 2 O, which was explained on the basis of the formation of a transient carbene intermediate according to DFT studies [37].…”

“…Surprisingly, dicarboxylate silver compounds, [Ag(L R )], were instead obtained, which were characterized as coordination polymeric species in the solid-state [37]. In solution, the C 2 -H group of imidazolium in [Ag(L R )] complexes experienced a fast H -D exchange with D 2 O, which was explained on the basis of the formation of a transient carbene intermediate according to DFT studies [37]. This prompted us to explore the reactivity of [Ag(L R )] with a base like aqueous sodium hydroxide in a NMR tube.…”

“…Following our interest in the investigation of complexes containing amino acid-derived ligands [32][33][34][35][36] and their medicinal applications [37,38], we decided to explore the preparation of new silver complexes containing chiral NHC R ligands, where NHC R is a N-heterocyclic carbene of 2,2 ′ -(1H-2λ 3 ,3λ 4 -imidazole-1,3-diyl)dicarboxylate type (Scheme 1). Here, we present the synthesis and characterization of new watersoluble silver complexes Na 3 [Ag(NHC R ) 2 ] (R = H, 2a), Na 3 [Ag{(S,S)-NHC R } 2 ] (R = Me, 2b; i Pr, 2c; i Bu, 2d; s Bu, 2e) and Na 3 [Ag{(R,R)-NHC R } 2 ] (R = Me, 2b'; i Pr, 2c').…”

Development of porous silver nanoparticle/polycaprolactone/polyvinyl alcohol coatings for prophylaxis in titanium interconnected samples for dental implants

“…Similar mechanisms are reported for P. aeruginosa 28 . In addition, the authors have also investigated the role of silver as antimicrobial in a recent publication to elucidate its mechanism of action as a potential therapeutic agent [41].…”