title: Formation of water-soluble pincer silver(I)-carbene complexes: a novel antimicrobial agent.
abstract: 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.
authors.affiliation: Departments of Chemistry and Biology, University of Akron, Akron, Ohio 44325, USA.
authors.forename: Abdulkareem
authors.initials: A
authors.lastname: Melaiye
authors.forename: Richard S
authors.initials: RS
authors.lastname: Simons
authors.forename: Amy
authors.initials: A
authors.lastname: Milsted
authors.forename: Francesco
authors.initials: F
authors.lastname: Pingitore
authors.forename: Chrys
authors.initials: C
authors.lastname: Wesdemiotis
authors.forename: Claire A
authors.initials: CA
authors.lastname: Tessier
authors.forename: Wiley J
authors.initials: WJ
authors.lastname: Youngs
mesh_terms: 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
chemical_list: 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