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Compound Information

Compound Name: 1-[N-(3-Ammoniopropyl)-N-(n-propyl)amino]diazen-1-ium-1,2-diolate

Compound

Figure: PAPA/NO (also NOC-15) Structure

  1. Category Information
  2. Nickname: PAPA/NO (also NOC-15)
  3. CAS Registry Number: 146672-58-4, 199666-32-5
  4. Molecular Formula: C6H16N4O2
  5. Molecular Weight: 176
  6. Half-life at pH 7.4 and 37oC:
  7. Moles of NO/Mole of Compound: 2
  8. Solubility: basic solutions
  9. UV Spectrum

          λmax(nm):

          ε(mM-1cm-1):      

    250 in 0.01 M NaOH

    8.1
  10. X-Ray Crystallographic Data:
  11. Special Comments: A reagent for producing reliable fluxes of NO in aqueous solutions or culture media with an intermediate half-life (about 15 min). This compound is known to be commercially available.

Reference and Patent Information

Reference TypeKeywordsReferenceText
BiologicalAntileukemic Shami, P. J.; Sauls, D. L.; Weinberg, J. B. Schedule and concentration-dependent induction of apoptosis in leukemia cells by nitric oxide. Leukemia 1998, 12, 1461-1466. Pubmed Abstract
BiologicalAntimicrobial Ogawa, R.; Pacelli, R.; Espey, M. G.; Miranda, K. M.; Friedman, N.; Kim, S. M.; Cox, G.; Mitchell, J. B.; Wink, D. A.; Russo, A. Comparison of control of Listeria by nitric oxide redox chemistry from murine macrophages and NO donors: insights into Listeriocidal activity of oxidative and nitrosative stress. Free Radical Biol. Med. 2001, 30, 268-276. Pubmed Abstract
BiologicalAntioxidant Korytowski W.; Zareba M.; Girotti A.W. Inhibition of free radical-mediated cholesterol peroxidation by diazeniumdiolate-derived nitric oxide: effect of release rate on mechanism of action in a membrane system. Chem. Res. Toxicol. 2000, 13, 1265-1274. Pubmed Abstract
BiologicalAntioxidant Goss, S. P.; Hogg, N.; Kalyanaraman, B. The effect of nitric oxide release rates on the oxidation of human low density lipoprotein. J. Biol. Chem. 1997, 272, 21647-21653. Pubmed Abstract
BiologicalCytostasis Mooradian, D. L.; Hutsell, T. C.; Keefer, L. K. Nitric oxide (NO) donor molecules: effect of NO release rate on vascular smooth muscle cell proliferation in vitro. J. Cardiovasc. Pharmacol. 1995, 25, 674-678. Pubmed Abstract
BiologicalErectile Function Champion, H. C.; Bivalacqua, T. J.; Wang, R.; Kadowitz, P. J.; Keefer, L. K.; Saavedra, J. E.; Hrabie, J. A.; Doherty, P. C.; Hellstrom, W. J. G. Induction of penile erection by intracavernosal and transurethral administration of novel nitric oxide donors in the cat. J. Urol. 1999, 161, 2013-2019. Pubmed Abstract
BiologicalGlutathionylation of Proteins Townsend, D. M.; Findlay, V. J.; Fazilev, F.; Ogle, M.; Fraser, J.; Saavedra, J. E.; Ji, X.; Keefer, L. K.; Tew, K.D. A glutathione S-transferase p-activated prodrug causes kinase activation concurrent with S-glutathionylation of proteins. Mol. Pharmacol. 2006, 69 (2), 501-508. Pubmed Abstract
Chemical  Hrabie, J. A.; Klose, J. R.; Wink, D. A.; Keefer, L. K. New nitric oxide-releasing zwitterions derived from polyamines. J. Org. Chem. 1993, 58, 1472-1476.
Chemical  Keefer, L. K.; Nims, R. W.; Davies, K. M.; Wink, D. A. "NONOates" (1-substituted diazen-1-ium-1,2-diolates) as nitric oxide donors: Convenient nitric oxide dosage forms. Methods Enzymol. 1996, 268, 281-293. Pubmed Abstract
Patent  Keefer, L. K.; Hrabie, J. A. Complexes of nitric oxide with polyamines. U.S. Patent 5,155,137, October 13, 1992. Patent 5155137 Full Text
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