Formation of water-soluble pincer silver(I)-carbene complexes: a novel antimicrobial agent.
Silver(I)-2,6-bis(ethanolimidazolemethyl)pyridine hydroxide (4a) and silver(I)-2,6-bis(propanolimidazolemethyl)pyridine hydroxide (4b) are water-soluble silver(I)-carbene complexes that were synthesized in high yield by reacting silver(I) oxide with N-substituted pincer ligands 3 (a = 2,6-bis(ethanolimidazoliummethyl)pyridine diiodide, b = 2,6-bis(propanolimidazoliummethylpyridine)pyridine dibromide). The X-ray crystal structure of 4a is a one-dimensional linear polymer, whereas the mass spectroscopy confirms a monomer in the gas phase. A change in the anion of 4a from a hydroxide to a hexafluorophosphate formed a silver(I)-carbene complex 4c that is dimeric in structure and insoluble in water. The bactericidal activities of the water-soluble silver(I)-carbene complexes were found to be improved over that of silver nitrate.
Melaiye
Abdulkareem
A
Departments of Chemistry and Biology, University of Akron, Akron, Ohio 44325, USA.
Simons
Richard S
RS
Milsted
Amy
A
Pingitore
Francesco
F
Wesdemiotis
Chrys
C
Tessier
Claire A
CA
Youngs
Wiley J
WJ
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D019281:Dimerization; D004926:Escherichia coli / Q000187:drug effects; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012995:Solubility; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship; D014867:Water
D000900:Anti-Bacterial Agents; D007093:Imidazoles; D009942:Organometallic Compounds; D011725:Pyridines; C483199:silver(I)-2,6-bis(ethanolimidazolemethyl)pyridine hydroxide; C483200:silver(I)-2,6-bis(propanolimidazolinemethyl)pyridine hydroxide; D014867:Water