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Chemical Compound Review:

DEPMPO 5-diethoxyphosphoryl-5- methyl-1-oxido-3,4...

Synonyms: ACMC-209dfq, ANW-21684, CTK8B0891, AKOS015839002, AC1L3P3Z, ...

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Disease relevance of Diethyl (3,4-dihydro-2-methyl-2H-pyrrol-2-yl)phosphonate N-oxide

Cellular toxicity, pharmacokinetics, and the in vitro and in vivo stability of the SO3*- spin adduct of the spin trap, 5-diethoxyphosphoryl-5-methyl-1-pyrroline-n-oxide (DEPMPO), was investigated, and the results were compared with those of the widely used spin trap 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) [1].

High impact information on Diethyl (3,4-dihydro-2-methyl-2H-pyrrol-2-yl)phosphonate N-oxide

The mechanism of superoxide generation by endothelial nitric oxide synthase (eNOS) was investigated by the electron spin resonance spin-trapping technique using 5-diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide [2].
Here, we demonstrate using electron spin resonance spin-trapping with 5-diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide that pterin-free nNOS generates superoxide from the reductase and the oxygenase domain by a calcium/calmodulin-dependent mechanism [3].
In the present study we compared the effects on AChE activity of four free radical spin traps PBN, alpha-(4-pyridil-1)-N-tert-butyl nitrone (POBN), N-tert-butyl-alpha-(2-sulfophenyl)-nitrone (S-PBN) and 5-diethoxyphosphoryl-5-methyl-1-pyrroline-N-oxide (DEPMPO) [4].
Electroparamagnetic resonance (EPR) with the O(2)(-) spin trap 5-diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide demonstrated that formation of superoxide anion was increased more than 2-fold in the failing (P < .001 vs. nonfailing) myocardium [5].
The importance of protein kinase C, phospholipase C, and phospholipase D for elevation of respiratory burst was also demonstrated by the EPR experiments using the spin trap 5-diethoxyphosphoryl-5-methyl-1-pyrroline-N-oxide (DEPMPO) [6].

Anatomical context of Diethyl (3,4-dihydro-2-methyl-2H-pyrrol-2-yl)phosphonate N-oxide

PP lymphoid cells were purified and stimulated with phorbol 12-myristate 13-acetate in the presence of spin trap 5-diethoxyphosphoryl-5-methyl-1-pyrroline-N-oxide (DEPMPO) [7].

Associations of Diethyl (3,4-dihydro-2-methyl-2H-pyrrol-2-yl)phosphonate N-oxide with other chemical compounds

With DMPO or 5-diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide (DEPMPO) adducts were detected with carbon-centered lipid radical, with acyl radical, and with the hydroxyl radical [8].

Gene context of Diethyl (3,4-dihydro-2-methyl-2H-pyrrol-2-yl)phosphonate N-oxide

Superoxide production of eNOS and the rate constants for trapping of superoxide by MTHF were determined with electron paramagnetic resonance using 5-diethoxyphosphoryl-5-methyl-1-pyrroline-N-oxide (DEPMPO) as spin trap for superoxide [9].

References

Evaluation of DEPMPO as a spin trapping agent in biological systems. Liu, K.J., Miyake, M., Panz, T., Swartz, H. Free Radic. Biol. Med. (1999) [Pubmed]
Superoxide generation by endothelial nitric oxide synthase: the influence of cofactors. Vásquez-Vivar, J., Kalyanaraman, B., Martásek, P., Hogg, N., Masters, B.S., Karoui, H., Tordo, P., Pritchard, K.A. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
Tetrahydrobiopterin-dependent inhibition of superoxide generation from neuronal nitric oxide synthase. Vásquez-Vivar, J., Hogg, N., Martásek, P., Karoui, H., Pritchard, K.A., Kalyanaraman, B. J. Biol. Chem. (1999) [Pubmed]
Atypical effect of some spin trapping agents: reversible inhibition of acetylcholinesterase. Milatovic, D., Radic, Z., Zivin, M., Dettbarn, W.D. Free Radic. Biol. Med. (2000) [Pubmed]
Increased reactive oxygen species production and functional alterations in antioxidant enzymes in human failing myocardium. Sam, F., Kerstetter, D.L., Pimental, D.R., Mulukutla, S., Tabaee, A., Bristow, M.R., Colucci, W.S., Sawyer, D.B. J. Card. Fail. (2005) [Pubmed]
The effects of aliphatic (n-nonane), naphtenic (1,2, 4-trimethylcyclohexane), and aromatic (1,2,4-trimethylbenzene) hydrocarbons on respiratory burst in human neutrophil granulocytes. Myhre, O., Vestad, T.A., Sagstuen, E., Aarnes, H., Fonnum, F. Toxicol. Appl. Pharmacol. (2000) [Pubmed]
Priming of Peyer's patch lymphoid cells by hemorrhagic shock and resuscitation to produce superoxide radical. Chamulitrat, W., Miller, H.I., McDonough, K.H. Shock (1999) [Pubmed]
Lipid radicals: properties and detection by spin trapping. Stolze, K., Udilova, N., Nohl, H. Acta Biochim. Pol. (2000) [Pubmed]
Folic acid reverts dysfunction of endothelial nitric oxide synthase. Stroes, E.S., van Faassen, E.E., Yo, M., Martasek, P., Boer, P., Govers, R., Rabelink, T.J. Circ. Res. (2000) [Pubmed]

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