title: New glycosidase activated nitric oxide donors: glycose and 3-morphorlinosydnonimine conjugates.
abstract: [reaction: see text] To achieve site specific delivery of nitric oxide (NO), a new class of glycosidase activated NO donors has been developed. Glucose, galactose, and N-acetylneuraminic acid were covalently coupled to 3-morphorlinosydnonimine (SIN-1), a mesoionic heterocyclic NO donor, via a carbamate linkage at the anomeric position. The beta-glycosides were successfully prepared for these conjugates, while the alpha-glycosidic compounds were very unstable. The new stable sugar-NO conjugates could release NO in the presence of glycosidases. Such NO prodrugs may be used as enzyme activated NO donors in biomedical research.
authors.affiliation: Department of Biochemistry, The Ohio State University, Columbus, Ohio 43210, USA.
authors.forename: T Bill
authors.initials: TB
authors.lastname: Cai
authors.forename: Dongning
authors.initials: D
authors.lastname: Lu
authors.forename: Xiaoping
authors.initials: X
authors.lastname: Tang
authors.forename: Yalong
authors.initials: Y
authors.lastname: Zhang
authors.forename: Megan
authors.initials: M
authors.lastname: Landerholm
authors.forename: Peng George
authors.initials: PG
authors.lastname: Wang
mesh_terms: D002384:Catalysis; D006026:Glycoside Hydrolases / Q000378:metabolism*; D006027:Glycosides / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D008981:Molsidomine / Q000031:analogs & derivatives* / Q000737:chemistry; D020030:Nitric Oxide Donors / Q000138:chemical synthesis* / Q000378:metabolism; D011355:Prodrugs / Q000737:chemistry
chemical_list: D006027:Glycosides; D020030:Nitric Oxide Donors; D011355:Prodrugs; C002385:linsidomine; D008981:Molsidomine; D006026:Glycoside Hydrolases