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- Title
Novel Benzyl- or 4-Cyanobenzyl-Substituted N-Heterocyclic (Bromo)(carbene)silver(I) and (Carbene)(chloro)gold(I) Complexes: Synthesis and Preliminary Cytotoxicity Studies.
- Authors
Patil, Siddappa; Deally, Anthony; Hackenberg, Frauke; Kaps, Leonard; Müller-Bunz, Helge; Schobert, Rainer; Tacke, Matthias
- Abstract
N-Heterocyclic carbene (NHC) complexes bromo(1,3-dibenzyl-1,3-dihydro-2 H-imidazol-2-ylidene)silver(I) ( 2a), bromo[1-(4-cyanobenzyl)-3-methyl-1,3-dihydro-2 H-imidazol-2-ylidene]silver(I) ( 2b), and bromo[1-(4-cyanobenzyl)-3-methyl-1,3-dihydro-2 H-benzimidazol-2-ylidene]silver(I) ( 2c) were prepared by the reaction of 1,3-dibenzyl-1 H-imidazol-3-ium bromide ( 1a), 3-(4-cyanobenzyl)-1-methyl-1 H-imidazol-3-ium bromide ( 1b), and 3-(4-cyanobenzyl)-1-methyl-1 H-benzimidazol-3-ium bromide ( 1c), respectively, with silver(I) oxide. NHC Complexes chloro(1,3-dibenzyl-1,3-dihydro-2 H-imidazol-2-ylidene)gold(I) ( 3a), chloro[1-(4-cyanobenzyl)-3-methyl-1,3-dihydro-2 H-imidazol-2-ylidene]gold(I) ( 3b), and chloro[1-(4-cyanobenzyl)-3-methyl-1,3-dihydro-2 H-benzimidazol-2-ylidene]gold(I) ( 3c) were prepared via transmetallation of corresponding (bromo)(NHC)silver(I) complexes with chloro(dimethylsulfido)gold(I). The complex 3a was characterized in two polymorphic forms by single-crystal X-ray diffraction showing two rotamers in the solid state. The cytotoxicities of all three bromo(NHC)silver(I) complexes and three (chloro)(NHC)gold(I) complexes were investigated through 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2 H-tetrazolium bormide (MTT)-based preliminary in vitro testing on the Caki-1 cell line in order to determine their IC50 values. (Bromo)(NHC)silver(I) complexes 2a- 2c and (chloro)(NHC)gold(I) complexes 3a- 3c were found to have IC50 values of 27±2, 28±2, 34±6, 10±1, 12±5, and 12±3 μ M, respectively, on the Caki-1 cell line.
- Subjects
GOLD compounds; BROMIDES; POLYMORPHISM (Crystallography); X-ray diffraction; CELL lines
- Publication
Helvetica Chimica Acta, 2011, Vol 94, Issue 9, p1551
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201100107