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Compound Information

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

Figure: AcOM-PYRRO/NO Structure

  1. Category Information
  2. Nickname: AcOM-PYRRO/NO
  3. CAS Registry Number: 259686-42-5
  4. Molecular Formula: C7H13N3O4
  5. Molecular Weight: 203
  6. Half-life at pH 7.4 and 37oC:
  7. Moles of NO/Mole of Compound: 2 in presence of porcine liver esterase
  8. Solubility: very soluble in organic solvents
  9. UV Spectrum

          λmax(nm):

          ε(mM-1cm-1):
     

    256 in H2O

    7.8
  10. X-Ray Crystallographic Data:
  11. Special Comments: Cell penetrant NO prodrug, that is metabolically activated by esterases. Possesses antileukemic activity in vitro. Inhibited by oxidized LDL-induced apotosis in cultured endothelial cells.

Reference and Patent Information

Reference TypeKeywordsReferenceText
Biological  Saavedra, J. E.; Shami, P. J.; Wang, L. Y.; Davies, K. M.; Booth, M. N.; Citro, M. L.; Keefer, L. K. Esterase-sensitive nitric oxide donors of the diazeniumdiolate family: In vitro antileukemic activity. J. Med. Chem. 2000, 43, 261-269. Pubmed Abstract
Biological  Kotamraju, S.; Hogg, N.; Joseph, J.; Keefer, L. K.; Kalyanaraman, B. Inhibition of oxidized low-density lipoprotein-induced apoptosis in endothelial cells by nitric oxide. Peroxyl radical scavenging as an antiapoptotic mechanism. J. Biol. Chem. 2001, 276, 17316-17323. Pubmed Abstract
Chemical  Saavedra, J. E.; Shami, P. J.; Wang, L. Y.; Davies, K. M.; Booth, M. N.; Citro, M. L.; Keefer, L. K. Esterase-sensitive nitric oxide donors of the diazeniumdiolate family: In vitro antileukemic activity. J. Med. Chem. 2000, 43, 261-269. Pubmed Abstract
Patent  Keefer, L. K.; Dunams, T. M.; Saavedra, J. E. Oxygen-substituted derivatives of nucleophile-nitric oxide adducts as nitric oxide donor prodrugs. U.S. Patent 5,366,997, November 22, 1994. Patent 5366997 Full Text
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