New glycosidase activated nitric oxide donors: glycose and 3-morphorlinosydnonimine conjugates.
[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.
Cai
T Bill
TB
Department of Biochemistry, The Ohio State University, Columbus, Ohio 43210, USA.
Lu
Dongning
D
Tang
Xiaoping
X
Zhang
Yalong
Y
Landerholm
Megan
M
Wang
Peng George
PG
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
D006027:Glycosides; D020030:Nitric Oxide Donors; D011355:Prodrugs; C002385:linsidomine; D008981:Molsidomine; D006026:Glycoside Hydrolases