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Compound Information

Compound Name: O2-Vinyl 1-(Pyrrolidin-1-yl)diazen-1-ium-1,2-diolate

Compound

Figure: V-PYRRO/NO Structure

  1. Category Information
  2. Nickname: V-PYRRO/NO
  3. CAS Registry Number: 179344-98-0
  4. Molecular Formula: C6H11N3O2
  5. Molecular Weight: 157
  6. Half-life at pH 7.4 and 37oC:
  7. Moles of NO/Mole of Compound: 2
  8. Solubility: 5 mg/mL of water at 25oC; 12 mg/mL of 10% aqueous ethanol; 1 g/mL of DMSO
  9. UV Spectrum

          λmax(nm):

          ε(mM-1cm-1):      

    268 in H2O

    9.7
  10. X-Ray Crystallographic Data:
  11. Special Comments: Metabolically activated for NO release by cytochrome P450. V-PYRRO/NO proved hepatoprotective in various in vivo liver injury models. It also protected the kidneys from acetaminophen toxicity in mice. This compound is known to be commercially available.

Reference and Patent Information

Reference TypeKeywordsReferenceText
Biological  Shokolenko, I.; Oberyszyn, T. M.; D^Ambrosio, S. M.; Saavedra, J. E.; Keefer, L. K.; LeDoux, S. P.; Wilson, G. L.; Robertson, F. M. Protection of human keratinocyte mtDNA by low-level nitric oxide. Nitric Oxide 2001, 5, 555-560. Pubmed Abstract
Biological  Kim, Y. M.; Kim, T. H.; Chung, H. T.; Talanian, R. V.; Yin, X. M.; Billiar, T. R. Nitric oxide prevents tumor necrosis factor α-induced rat hepatocyte apoptosis by the interruption of mitochondrial apoptotic signaling through S-nitrosylation of caspase-8. Hepatology 2000, 32, 770-778. Pubmed Abstract
BiologicalCYP-Mediated Metabolism Inami, K.; Nims, R. W.; Srinivasan, A.;Citro, M. L.; Saavedra, J. E.; Cederbaum, A. I.; Keefer, L. K. Metabolism of a liver-selective nitric oxide-releasing agent, V-PYRRO/NO, by human microsomal cytochromes P450. Nitric Oxide 2006, Mar 16, [Epub ahead of print] Pubmed Abstract
BiologicalHepatoprotection Saavedra, J. E.; Billiar, T. R.; Williams, D. L.; Kim, Y. M.; Watkins, S. C.; Keefer, L. K. Targeting nitric oxide (NO) delivery in vivo. Design of a liver-selective NO donor prodrug that blocks tumor necrosis factor-alpha-induced apoptosis and toxicity in the liver. J. Med. Chem. 1997, 40, 1947-1954. Pubmed Abstract
BiologicalHepatoprotection (transplantation model) Ricciardi, R.; Foley, D. P.; Quarfordt, S. H.; Saavedra, J. E.; Keefer, L. K.; Wheeler, S. M.; Donohue, S. E.; Callery, M. P.; Meyers, W. C. V-PYRRO/NO: an hepato-selective nitric oxide donor improves porcine liver hemodynamics and function after ischemia reperfusion. Transplantation 2001, 71, 193-198. Pubmed Abstract
BiologicalMitigates Arsenic Toxicity in Cultured Liver Cells Qu, W.; Liu, J.; Fuquay, R.; Saavedra, J. E.; Keefer, L. K.; Waalkes, M. P. The nitric oxide prodrug, V-PYRRO/NO, mitigates arsenic-induced liver cell toxicity and apoptosis. Can. Lett. 2007, 256 (2), 238-245. Pubmed Abstract
BiologicalPharmacokinetics Stinson, S. F.; House, T.; Bramhall, C.; Saavedra, J. E.; Keefer, L. K.; Nims, R. W. Plasma pharmacokinetics of a liver-selective nitric oxide-donating diazeniumdiolate in the male C57BL/6 mouse. Xenobiotica 2002, 32, 339-347. Pubmed Abstract
BiologicalProtection of Kidney from Acetominophen Toxicity Li, C.; Liu, J.; Saavedra, J. E.; Keefer, L. K.; Waalkes, M. P. The nitric oxide donor, V-PYRRO/NO, protects against acetaminophen-induced nephrotoxicity in mice. Toxicology 2003, 189 (3), 173-180. Pubmed Abstract
BiologicalProtection of Liver from Acetominophen Toxicity Liu, J.; Li, C.; Waalkes, M. P.; Clark, J.; Myers, P.; Saavedra, J. E.; Keefer, L. K. The nitric oxide donor, V-PYRRO/NO, protects against acetaminophen-induced hepatotoxicity in mice. Hepatology 2003, 37 (2), 324-333. Pubmed Abstract
BiologicalProtection of Liver from Endotoxin Liu, J.; Saavedra, J. E.; Lu, T.; Song, J.G.; Clark, J.; Waalkes, M. P.; Keefer, L. K. O2-Vinyl 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate protection against D-galactosamine/ endotoxin-induced hepatoxicity in mice: genomic analysis using microarrays. J. Pharmacol. Exp. Ther. 2002, 300, 18-25. Pubmed Abstract
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