Compound Information

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

Figure: AcOM-PYRRO/NO Structure

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

λ_max(nm):

ε(mM^-1cm^-1):

256 in H₂O

7.8
X-Ray Crystallographic Data:
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 Type	Reference	Text
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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