| Abstract
| - The enediamine tautomer of a variety of substituted amidine free bases reacts with nitric oxide(NO) to produce compounds containing a carbon-bound diazeniumdiolate [R1R2R3C−N(O)NO-]functional group (previously called “nitrosohydroxylamines”). The new reaction has been shown tobe quite general, although the nature of the products does vary. Amidines containing more thanone replaceable hydrogen produce polydiazeniumdiolates as intermolecular salts, while those inwhich only one diazeniumdiolation can occur provide zwitterionic salts. These diazeniumdiolatedamidines are shown to be useful NO donor compounds which undergo very slow spontaneousdissociation on dissolution in pH 7.4 phosphate buffer to produce mixtures of NO and nitrous oxidecontaining mostly NO. The most advantageous manifestation of the new discovery is the preparationof the monodiazeniumdiolated amidine zwitterions. Reaction of the medically relevant α-adrenergicagonists tetrahydrozoline and idazoxan produced monodiazeniumdiolated amidine zwitterions fromwhich NO release was observed for up to 28 days and showed little sign of ending. The reactionshould be applicable to a variety of pharmaceutical agents, including NO synthase inhibitors,antitumor agents, and antibacterials.
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