Characterization of the high resolution ESR spectra of the methoxyl radical adducts of 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO)

Free Radical Research

Volumn 37, Issue 7, 2003, Pages 705-712

  Dikalov, Sergey ^a   Tordo, Paul ^b   Motten, Ann ^a   Mason, Ronald P ^a  

^a NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Alkoxyl radical; DEPMPO; Oxygen 17; Radical adduct; Spin trap; Superhyperfine structure

Indexed keywords

5 DIETHOXYPHOSPHORYL 5 METHYL 1 PYRROLINE 1 OXIDE; ALCOHOL; METHANOL; OXYGEN RADICAL; PHOSPHATE; PROTON;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; COMPUTER SIMULATION; CONTROLLED STUDY; DIASTEREOISOMER; ELECTRON SPIN RESONANCE; SPECTROSCOPY; SPIN TRAPPING; STRUCTURE ANALYSIS; SYNTHESIS;

ALCOHOLS; COMPUTER SIMULATION; CYCLIC N-OXIDES; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; MAGNETICS; METHANOL; MODELS, CHEMICAL; OXYGEN; PROTEIN ISOFORMS; PROTONS; SPIN LABELS; STEREOISOMERISM;

EID: 0037799808     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.1080/1071576031000097508     Document Type: Article

References (19)

1. Janzen, E.G. and Haire, D.L. (1990) "Two decades of spin trapping", Adv. Free Radic. Chem. 1, 253-295.
2. Janzen, E.G. (1971) "Spin trapping", Acc. Chem. Res. 4, 31-40.
3. Dikalov, S.I. and Mason, R.P. (1999) "Reassignment of organic peroxyl radical adducts", Free Radic. Biol. Med. 27, 864-872.
4. Ledwith, A., Russell, P.J. and Sutcliffe, L.H. (1973) "Alkoxy radical intermediates in the thermal and photochemical oxidation of alcohols", Proc. R. Soc. Lond. A. 332, 151-166.
5. Grossi, L., Strazzari, S., Gilbert, B.C. and Whitwood, A.C. (1998) "Oxiranylcarbinyl radicals from allyloxyl radical cyclization: characterization and kinetic information via ESR spectroscopy", J. Org. Chem. 63, 8366-8372.
6. Kotake, Y. and Janzen, E.G. (1991) "Decay and fate of the hydroxyl radical adduct of.alpha.-phenyl-N-tert-butylnitrone in aqueous media", J. Am. Chem. Soc. 113, 9503-9506.
7. Janzen, E.G., Krygsman, P.H., Lindsay, D.A. and Haire, D.L. (1990) "Detection of alkyl, alkoxyl, and alkyperoxyl radicals from the thermolysis of azobis(isobutyronitrile) by ESR/spin trapping. Evidence for double spin adducts from liquid-phase chromatography and mass spectroscopy", J. Am. Chem. Soc. 112, 8279-8284.
8. Frejaville, C., Karoui, H., Tuccio, B., Le Moigne, F., Culcasi, M., Pietri, S., Lauricella, R. and Tordo, P. (1994) "5-Diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide (DEPMPO) - a new phosphorylated nitrone for the efficient in vitro and in vivo spin-trapping of oxygen-centered radicals", J. Chem. Soc. Chem. Commun. 15, 1793-1794.
9. F. Chalier. PhD Thesis, University of Marseilles, Marseilles, France.
10. Frejaville, C., Karoui, H., Tuccio, B., Le Moigne, F., Culcasi, M., Pietri, S., Lauricella, R. and Tordo, P. (1995) "5-(Diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide-a new efficient phosphorylated nitrone for the in vitro and in vivo spin trapping of oxygen-centered radicals", J. Med. Chem. 38, 258-265.
11. Vasquez-Vivar, J., Hogg, N., Marthasek, P., Karoui, H., Tordo, P., Pritchard, K.A. and Kalyanaraman, B. (1999) "Effect of redox-active drugs on superoxide generation from nitric oxide synthases: biological and toxicological implications", Free Radic. Res. 31, 607-617.
12. Makino, K., Hagiwara, T., Hagi, A., Nishi, M. and Murakami, A. (1990) "Cautionary note for DMPO spin trapping in the presence of iron ion", Biochem. Biophys. Res. Commun. 172, 1073-1080.
13. 4PO) with 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) as spin traps", Biochem. Int. 27, 651-659.
14. Duling, D.R. (1994) "Simulation of multiple isotropic spin-trap ESR spectra", J. Magn. Res. Series B 104, 105-110.
15. Hanna, P.M., Chamulitrat, W. and Mason, R.P. (1992) "When are metal ion-dependent hydroxyl and alkoxyl radical adducts of 5,5-dimethyl-1-pyrroline N-oxide artifacts?", Arch. Biochem. Biophys. 296, 640-644.
16. Kotake, Y., Kuwata, K. and Janzen, E.G. (1979) "Electron spin resonance spectra of diastereomeric nitroxyls produced by spin trapping hydroxyalkyl radicals", J. Phys. Chem. 83, 3024-3029.
17. Dikalov, S.I. and Mason, R.P. (2001) "Spin trapping of polyunsaturated fatty acid-derived peroxyl radicals. Reassignment to alkoxyl radical adducts", Free Radic. Biol. Med. 30, 187-197.
18. Haire, D.L., Oehler, U.M., Goldman, H.D., Dudley, R.L. and Janzen, E.G. (1988) "The 1st H-1 and N-14 ENDOR spectra of an oxygen-centered radical adduct of DMPO-type nitrones", Can. J. Chem. 66, 2395-2402.
19. 17O]Oxygen hyperfine structure for the hydroxyl and superoxide radical adducts of the spin traps DMPO, PBN and 4-POBN", Biochem. Biophys. Res. Commun. 141, 622-628.