National Institutes of Health, a Component of the US Dept. of Health & Human Services

Christian Bogdan

Larry K Keefer

Joseph E Saavedra

William G Rice

Xinhua Ji

Aloka Srinivasan

Provided are O-glycosylated 1-substituted diazen-1-ium-1,2-diolates (O-glycosylated diazeniumdiolates) having the formula:in which R is a saccharide, which is attached to the Oof the compound by the anomeric carbon of a pyranose ring or a furanose ring.

O2-glycosylated 1-substituted diazen-1-ium-1,2-diolates

Diazeniumdiolates, wherein the N position is substituted by an inorganic or organic moiety and the O -oxygen is bound to a substituted or unsubstituted aromatic group, are provided. Also provided are O -glycosylated 1-substituted diazen-1-ium-1,2-diolates (O -glycosylated diazeniumdiolates) and O -substituted 1-&lsqb;(2-carboxylato)pyrrolidin-1-yl&rsqb;diazen-1-ium-1,2-diolates (1-&lsqb;(2-carboxylato)pyrrolidin-1-yl&rsqb;diazeniumdiolates). The O -aryl diazeniumdiolates are stable with respect to the hydrolytic generation of nitric oxide in neutral to acidic solutions and generate nitric oxide in basic or nucleophilic environments or microenvironments. Also provided are compositions, including pharmaceutical compositions, comprising such compounds and methods of using such compounds.

O2-arylated or O2-glycosylated 1-substituted diazen-1-ium-1,2-diolates and O2-substituted 1-&lsqb;(2-carboxylato) pyrrolidin-1-yl&rsqb; diazen-1-ium-1,2-diolates

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Christian Bogdan