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Nitrogen-Based Diazeniumdiolates: Versatile Nitric Oxide-Releasing Compounds for Biomedical Research and Potential Clinical Applications

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Larry K. Keefer

The Chemistry Section, Laboratory of Comparative Carcinogenesis, National Cancer Institute, Frederick, MD 21702-5946

Joseph E. Saavedra

Intramural Research Support Program, SAIC, National Cancer Institute, Frederick, MD 21702-5946

J. Chem. Educ., 2002, 79 (12), p 1427

DOI: 10.1021/ed079p1427

Publication Date (Web): December 1, 2002

Abstract

Nitric oxide-generating ions of the nitrogen-diazeniumdiolate class with the general structure R¹R²N-[N(O)NO]¹ have been prepared by exposing primary, secondary, and polyamines to nitric oxide (NO). The resulting complexes regenerate bioactive NO at physiological pH with half-lives ranging from 2 seconds to 20 hours. An important goal in our research is to deliver NO to a specific organ or cell type where it is needed without affecting other NO-sensitive parts of the anatomy. By taking advantage of the remarkable chemical versatility of diazeniumdiolates, we have developed general strategies to prepare either tissue-selective NO donor drugs or materials containing NO delivery agents that can be physically placed near the target sites. Inhibition of blood coagulation, induction of penile erection, relief of pulmonary hypertension, and reversal of cerebral vasospasm are a few examples of their potential clinical applications.