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Compound Information

Compound Name: 1-{N-[3-Aminopropyl]-N-[4-(3-aminopropylammoniobutyl)]}diazen-1-ium-1,2-diolate

Compound

Figure: SPER/NO Structure

  1. Category Information
  2. Nickname: SPER/NO
  3. CAS Registry Number: 136587-13-8
  4. Molecular Formula: C10H26N6O2.H2O
  5. Molecular Weight: 280
  6. Half-life at pH 7.4 and 37oC: 10-90 min
  7. Moles of NO/Mole of Compound: 2
  8. Solubility: Water
  9. UV Spectrum

          λmax(nm):

          ε(mM-1cm-1):      

    252 in pH 7.4 phosphate buffer

    8.5
  10. X-Ray Crystallographic Data:
  11. Special Comments: Dissociates to bioactive spermine and NO in aqueous solutions or culture media with a somewhat variable half-life (10-90 min) that depends on concentration and other medium effects. This compound is known to be commercially available.

Reference and Patent Information

Reference TypeKeywordsReferenceText
Biological  Sarkar, R.; Meinberg, E. G.; Stanley, J. C.; Gordon, D.; Webb, R. C. Nitric oxide reversibly inhibits the migration of cultured vascular smooth muscle cells. Circ. Res. 1996, 78, 225-230. Pubmed Abstract
BiologicalAntioxidant Goss, S. P.; Hogg, N.; Kalyanaraman, B. The antioxidant effect of spermine NONOate in human low-density lipoprotein. Chem. Res. Toxicol. 1995, 8, 800-806. Pubmed Abstract
BiologicalAntioxidant Hogg, N.; Struck, A.; Goss, S. P.; Santanam, N.; Joseph, J.; Parthasarathy, S.; Kalyanaraman, B. Inhibition of macrophage-dependent low density lipoprotein oxidation by nitric-oxide donors. J. Lipid Res. 1995, 36, 1756-1762. 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
BiologicalAntiplatelet Diodati, J. G.; Quyyumi, A. A.; Hussain, N.; Keefer, L. K. Complexes of nitric oxide with nucleophiles as agents for the controlled biological release of nitric oxide: Antiplatelet effect. Thromb. Haemostasis 1993, 70, 654-658. Pubmed Abstract
BiologicalCytostasis Yin, Z. L.; Dusting, G. J. A nitric oxide donor (spermine-NONOate) prevents the formation of neointima in rabbit carotid artery. Clin. Exp. Pharmacol. Physiol. 1997, 24, 436-438. 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
BiologicalVasodilation Diodati, J. G.; Quyyumi, A. A.; Keefer, L. K. Complexes of nitric oxide with nucleophiles as agents for the controlled biological release of nitric oxide: hemodynamic effect in the rabbit. J. Cardiovasc. Pharmacol. 1993, 22, 287-292. Pubmed Abstract
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
Chemical  Davies, K. M.; Wink, D. A.; Saavedra, J. E.; Keefer, L. K. Chemistry of the diazeniumdiolates. 2. Kinetics and mechanisms of dissociation in aqueous solution. J. Am. Chem. Soc. 2001, 123, 5473-5481. Pubmed Abstract
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