Compound Information

Compound Name: O²-(Acetoxymethyl) 1-(N, N-Diethylamino)diazen-1-ium-1,2-diolate

Figure: AcOM-DEA/NO Structure

Category Information
Nickname: AcOM-DEA/NO
CAS Registry Number: 213768-16-2
Molecular Formula: C₇H₁₅N₃O₄
Molecular Weight: 205
Half-life at pH 7.4 and 37^oC:
Moles of NO/Mole of Compound: 2 in presence of esterases
Solubility: Soluble in organic solvents, sparingly soluble in water.
UV Spectrum

λ_max(nm):

ε(mM^-1cm^-1):

230 in H₂O

7.6
X-Ray Crystallographic Data:
Special Comments: Cell penetrant NO prodrug. Metabolically activated by esterase. Possesses antileukemic activity in vitro in HL-60 and U937 human leukemia cell lines. Inhibited oxidized LDL-induced apoptosis in cultured endothelial cells. This compound is known to be commercially available.

Reference Type	Keywords	Reference	Text
Biological	Antileukemic	Saavedra, J. E.; Shami, P. J.; Wang, L. Y.; Davies, K. M.; Booth, M. N.; Citro, M. L.; and 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	Antioxidant	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.; and 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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