Antimicrobial Properties of Amino-Acid-Derived N-Heterocyclic Carbene Silver Complexes.

Complexes {Ag[NHC Mes,R ]} n (R = H, 2a ; Me, 2b and 2b' ; i Pr, 2c ; i Bu, 2d ), were prepared by treatment of imidazolium precursor compounds [Im Mes,R ] (2-(3-mesityl-1 H -imidazol-3-ium-1-yl)acetate, 1a , ( S )-2- alkyl (3-mesityl-1 H -imidazol-3-ium-1-yl)acetate, 1b - d , and ( R )-2-methyl(3-mesityl-1 H -imidazol-3-ium-1-yl)acetate, 1b' , with Ag 2 O under appropriate conditions. They were characterised by analytical, spectroscopic (IR, 1 H, and 13 C NMR and polarimetry), and X-ray methods ( 2a ). In the solid state, 2a is a one-dimensional coordination polymer, in which the silver(I) cation is bonded to the carbene ligand and to the carboxylate group of a symmetry-related Ag[NHC Mes,H ] moiety. The coordination environment of the silver centre is well described by the DFT study of the dimeric model {Ag[NHC Mes,H ]} 2 . The antimicrobial properties of these complexes were evaluated versus Gram-negative bacteria E. coli and P. aeruginosa . From the observed MIC and MBC values (minimal inhibitory concentration and minimal bactericidal concentration, respectively), complex 2b' showed the best antimicrobial properties (eutomer), which were significantly better than those of its enantiomeric derivative 2b (distomer). Additionally, analysis of MIC and MBC values of 2a - d reveal a clear structure-antimicrobial effect relationship. Antimicrobial activity decreases when the steric properties of the R alkyl group in {Ag[NHC Mes,R ]} n increase.