Diazeniumdiolates as Research Tools

Our laboratory has developed an extensive library of diazeniumdiolates. Their preparation is based on a Lewis acid-base reaction. We use the Lewis acid (electron acceptor) property of nitric oxide (NO) to react it with a number of nucleophiles (electron donors) to generate adducts that release NO under physiological conditions. The chemical name of this class of compounds is "diazeniumdiolate."

Diazeniumdiolate salts are generally obtained as white powders, insoluble in most organic solvents, relatively stable at room temperature, but they release NO at predictable rates and extents upon dissolution in physiological media. Diazeniumdiolates may release up to 2 moles of NO per mole of compound. This quality has made them very useful research tools as reliable and stable sources of NO to probe into its protective or toxicological roles (view scheme.)

Depending upon the nucleophile used to prepare the ionic diazeniumdiolate, we obtain carbon-based diazeniumdiolates, nitrogen-based diazeniumdiolates, or polymer-based diazeniumdiolates:

C-based diazeniumdiolates
N-based Diazeniumdiolates
Polymer-based Diazeniumdiolates
Potential Clinical Applications