title: Synthesis, ocular effects, and nitric oxide donation of imidazole amidoximes.
abstract: Novel 1-R-imidazole-5-amidoximes and 1-R-5-cyano-imidazole-4-amidoximes (R: H, Me, Bn) were prepared from their corresponding nitriles and were tested for their efficacy to lower intraocular pressure (IOP) in rabbits. The ability of these compounds to donate nitric oxide (NO) was studied by observing the stimulation of formation of cyclic guanosine-3',5'-monophosphate (cGMP) in the incubation of porcine iris-ciliary body. In the incubation experiments, 1-methylimidazole-5-amidoxime and 1(H)-imidazole-4(5)-amidoxime stimulated formation of cGMP indicating NO donating ability of these compounds. 1-Methylimidazole-5-amidoxime lowered IOP significantly after intravitreal injection.
authors.affiliation: Department of Chemistry, University of Joensuu, PO Box 111, 80101 Joensuu, Finland.
authors.forename: L
authors.initials: L
authors.lastname: Oresmaa
authors.forename: H
authors.initials: H
authors.lastname: Kotikoski
authors.forename: M
authors.initials: M
authors.lastname: Haukka
authors.forename: O
authors.initials: O
authors.lastname: Oksala
authors.forename: E
authors.initials: E
authors.lastname: Pohjala
authors.forename: H
authors.initials: H
authors.lastname: Vapaatalo
authors.forename: E
authors.initials: E
authors.lastname: Moilanen
authors.forename: P
authors.initials: P
authors.lastname: Vainiotalo
authors.forename: P
authors.initials: P
authors.lastname: Aulaskari
mesh_terms: D000586:Amination; D000818:Animals; D006152:Cyclic GMP / Q000097:blood; D005123:Eye / Q000187:drug effects* / Q000378:metabolism*; D005260:Female; D007093:Imidazoles / Q000737:chemistry*; D007536:Isomerism; D008297:Male; D015394:Molecular Structure; D009566:Nitrates / Q000737:chemistry; D009569:Nitric Oxide / Q000378:metabolism*; D010091:Oximes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011817:Rabbits; D013329:Structure-Activity Relationship; D013552:Swine
chemical_list: D007093:Imidazoles; D009566:Nitrates; D010091:Oximes; D009569:Nitric Oxide; C029899:imidazole; D006152:Cyclic GMP