ESR and HPLC-EC analysis of ethanol oxidation to 1-hydroxyethyl radical: Rapid reduction and quantification of POBN and PBN nitroxides

Free Radical Biology and Medicine

Volumn 25, Issue 4-5, 1998, Pages 536-545

  Stoyanovsky, Detcho A ^a   Cederbaum, Arthur I ^a  

^a MOUNT SINAI SCHOOL OF MEDICINE   (United States)

Author keywords

1 Hydroxyethyl radical; Catalase; CYP2E1; Electrochemical; ESR; Ethanol; Free radicals; HPLC; Live r; Microsomes; PBN; POBN; SOD

Indexed keywords

1 HYDROXYETHYL RADICAL; ALCOHOL; ASCORBIC ACID; CATALASE; CYTOCHROME P450; HYDROXYLAMINE; NITROXIDE; PYRAZOLE; RADICAL; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG;

ALCOHOL OXIDATION; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; ELECTROCHEMICAL DETECTION; ELECTRON SPIN RESONANCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIVER MICROSOME; NONHUMAN; PRIORITY JOURNAL; RAT; REDUCTION;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 CYP2E1; ELECTRON SPIN RESONANCE SPECTROSCOPY; ETHANOL; KINETICS; MICROSOMES, LIVER; NITROGEN OXIDES; OXIDATION-REDUCTION; RATS; RATS, SPRAGUE-DAWLEY; SPIN LABELS;

ANIMALIA; CERVIDAE; PEROMYSCUS;

EID: 0032171255     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(98)00081-1     Document Type: Article

References (47)

1. Albano E., Tomasi A., Goria-Gatti L., Dianzani M.U. Spin trapping of free radical species produced during the microsomal metabolism of ethanol. Chem. Biol. Interact. 65:1988;223-234.
2. Albano E., Tomasi A., Goria-Gatti L., Poli G., Vannini V., Dianzani M.U. Free radical metabolism of alcohols by rat liver microsomes. Free. Radic. Res. Commun. 3:1987;243-249.
3. Albano E., Tomasi A., Persson J.O., Terelius Y., Goria-Gatti L., Ingelman-Sundberg M., Dianzani M.U. Role of ethanol-inducible cytochrome P450 (P450IIE1) in catalysing the free radical activation of aliphatic alcohols. Biochem. Pharmacol. 41:1991;1895-1902.
4. Reinke L.A., Lai E.K., DuBose C.M., McCay P.B. Reactive free radical generation in vivo in heart and liver of ethanol-fed rats Correlation with radical formation in vitro . Proc. Natl. Acad. Sci. USA. 84:1987;9223-9227.
5. Reinke L.A., Rau J.M., McCay P.B. Possible roles of free radicals in alcoholic tissue damage. Free Radic. Res. Commun. 9:1990;205-211.
6. Reinke L.A., Moore D.R., Hague C.M., McCay P.B. Metabolism of ethanol to 1-hydroxyethyl radicals in rat liver microsomes Comparative studies with three spin trapping agents . Free Radic. Res. Commun. 21:1994;213-222.
7. Rashba-Step J., Turro N.J., Cederbaum A.I. Increased NADPH- and NADH-dependent production of superoxide and hydroxyl radical by microsomes after chronic ethanol treatment. Arch. Biochem. Biophys. 300:1993;401-408.
8. Knecht K.T., Bradford B.U., Mason R.P., Thurman R.G. In vivo formation of a free radical metabolite of ethanol. Mol. Pharmacol. 38:1990;26-30.
9. Moore D.R., Reinke L.A., McCay P.B. Metabolism of ethanol to 1-hydroxyethyl radicals in vivo Detection with intravenous administration of alpha-(4-pyridyl-1-oxide)-n-t-butylnitrone . Mol. Pharmacol. 47:1995;1224-1230.
10. Albano E., Parola M., Comoglio A., Dianzani M.U. Evidence for the covalent binding of hydroxyethyl radicals to rat liver microsomal proteins. Alcohol Alcohol. 28:1993;453-459.
11. Moncada C., Torres V., Varghese G., Albano E., Israel Y. Ethanol-derived immunoreactive species formed by free radical mechanisms. Mol. Pharmacol. 46:1994;786-791.
12. Clot P., Bellomo G., Tabone M., Arico S., Albano E. Detection of antibodies against proteins modified by hydroxyethyl free radicals in patients with alcoholic cirrhosis. Gastroenterology. 108:1995;201-207.
13. Knecht K.T., Thurman R.G., Mason R.P. Role of superoxide and trace transition metals in the production of alpha-hydroxyethyl radical from ethanol by microsomes from alcohol dehydrogenase-deficient deermice. Arch. Biochem. Biophys. 303:1993;339-348.
14. Rao D.N., Yang M.X., Lasker J.M., Cederbaum A.I. 1-Hydroxyethyl radical formation during NADPH- and NADH-dependent oxidation of ethanol by human liver microsomes. Mol. Pharmacol. 49:1996;814-821.
15. Cederbaum A.I. Generation of active oxygen species and their possible role in alcohol hepatotoxicity. Alcohol Alcohol Suppl. 1:1991;291-296.
16. Cederbaum A.I. Oxygen radical generation by microsomes Role of iron and implications for alcohol metabolism and toxicity . Free Radic. Biol. Med. 7:1989;559-567.
17. Ekström G., Ingelman-Sundberg M. Rat liver microsomal NADPH-supported oxidase activity and lipid peroxidation dependent on ethanol-inducible cytochrome P450 (P450IIE1). Biochem. Pharmacol. 38:1989;1313-1318.
18. Ingelman-Sundberg M., Johnsson I. Mechanism of hydroxyl radical formation and ethanol oxidation by ethanol-inducible and other forms of rabbit liver microsomal cytochrome P450. J. Biol. Chem. 259:1984;6447-6458.
19. Reinke L.A., Kotake Y., McKay P.B., Janzen E.G. Spin-trapping studies of hepatic free radicals formed following the acute administration of ethanol to rats In vivo detection of 1-hydroxyethyl radicals with PBN . Free Radic. Biol. Med. 11:1991;31-39.
20. Bernofsky C., Bandara B.M. Spin trapping endogenous radicals in MC-1010 cells Evidence for hydroxyl radical and carbon-centered ascorbyl radical adducts . Mol. Cell. Biochem. 148:1995;155-164.
21. Sentjurc M., Mason R.P. Inhibition of radical adduct reduction and reoxidation of the corresponding hydroxylamines in in vivo spin trapping of carbon tetrachloride-derived radicals. Free Radic. Biol. Med. 13:1992;151-160.
22. Nakagawa K., Ishida S., Yokoyama H., Mori N., Niwa S., Tsuchihashi N. Rapid free radical reduction in the perfused rat liver. Free Radic. Res. 21:1994;169-176.
23. Rosen G.M., Rauckman E. Formation and reduction of a nitroxide radical by liver microsomes. Biochem. Pharmacol. 26:1977;675-678.
24. Iannone A., Tomasi A., Vannini V., Swartz H.M. Metabolism of nitroxide spin labels in subcellular fractions of rat liver II. Reduction in the cytosol . Biochim. Biophys. Acta. 1034:1990;290-293.
25. Iannone A., Hu H.P., Tomasi A., Vannini V., Swartz H.M. Metabolism of aqueous soluble nitroxides in hepatocytes Effects of cell integrity, oxygen, and structure of nitroxides . Biochim. Biophys. Acta. 991:1989;90-96.
26. Palakodety R.B., Clejan L.A., Krikun G., Feierman D.E., Cederbaum A.I. Characterization and identification of a pyrazole-inducible form of cytochrome P-450. J. Biol. Chem. 263:1988;878-884.
27. Finkelstein E., Rosen G.M., Rauckman E.J. Spin trapping of superoxide and hydroxyl radical Practical aspects . Arch. Biochem. Biophys. 200:1980;1-16.
28. Finkelstein E., Rosen G.M., Rauckman E.J. Production of hydroxyl radical by decomposition of superoxide spin trapped adducts. Mol. Pharmacol. 21:1982;262-265.
29. Saprin A.N., Piette L.H. Spin trapping and its application in the study of lipid peroxidation and free radical production with liver microsomes. Arch. Biochem. Biophys. 180:1977;480-492.
30. Adamic K., Bowman D.F., Gillan T., Ingold K.U. Kinetic applications of EPR spectroscopy I. Self-reactions of diethyl nitroxide radical . J. Am. Chem. Soc. 93:1970;902-908.
31. Bowman D.F., Gillan T., Ingold K.U. Kinetic applications of EPR spectroscopy III. Self-reactions of diethyl nitroxide radical . J. Am. Chem. Soc. 93:1971;6555-6561.
32. Yelinova V.I., Weiner L.M., Slepneva I.A., Levina A.S. Reversible modification of cysteine residues of NADPH-cytochrome P-450 reductase. Biochem. Biophys. Res. Commun. 193:1993;1044-1048.
33. Pou S., Ramos C.L., Gladwellm T., Renksm E., Centram M., Young D., Cohen M.S., Rosen G.M. A kinetic approach to the selection of a sensitive spin trapping system for the detection of hydroxyl radical. Anal. Biochem. 217:1994;76-83.
34. Morris S., Sosnovsky G., Hui B., Huber C.O., Swartz H.M. Chemical and electrochemical reduction of cyclic nitroxides (nitroxyls). J. Pharm. Sci. 80:1991;149-152.
35. Roberts J.S. Hydroxylamine derivatives. Barton D., Ollis W.D., Sutherland I.O. Comprehensive organic chemistry. Vol. 2:1979;228-245 Pergamon Press, LTD, Oxford.
36. Jaffe H.H. The ultraviolet spectra of substituted pyridine 1-oxides and their conjugate acids. J. Am. Chem. Soc. 77:1955;4451-4453.
37. Towell J., Kalyanaraman B. Detection of radical adducts of 5,5-dimethyl-1-pyrroline N-oxide by the combined use of high-performance liquid chromatography with electrochemical detection and electron spin resonance. Anal. Biochem. 196:1991;111-119.
38. Pritsos C.A., Constantinides P.P., Tritton T.R., Heimbrook D.C., Sartorelli A. Use of high-performance liquid chromatography to detect hydroxyl and superoxide radicals generated from mitomycin C. Anal. Biochem. 150:1985;294-299.
39. Stoyanovsky D.A., Goldman R., Jonnalagadda S.S., Day B.W., Claycamp H.G., Kagan V.E. Detection and characterization of the electron paramagnetic resonance-silent glutathionyl-5,5-dimethyl-1-pyrroline N-oxide adduct derived from redox cycling of phenoxyl radicals in model systems and HL-60 cells. Arch. Biochem. Biophys. 330:1996;3-11.
40. Iwahashi H., Parker C.E., Mason R.P., Tomer K.B. Combined liquid chromatography/electron paramagnetic resonance spectrometry/electrospray ionization mass spectrometry for radical identification. Anal. Chem. 64:1992;2244-2252.
41. Winston G.W., Cederbaum A.I. Evidence for two ethanol oxidizing pathways in reconstituted mixed-function oxidase systems. Pharmacol. Biochem. Behav. 18:1983;189-194.
42. Krikun G., Cederbaum A.I. Increased microsomal oxidation of alcohols after pyrazole preatment and its similarities to the induction by ethanol consumption. Biochim. Biophys. Acta. 801:1984;131-137.
43. Krikun G., Feierman D.E., Cederbaum A.I. Rat liver microsomal induction of the oxidation of drugs, alcohols and SDS-gel profiles after in vivo treatment with pyrazole and 4-methylpyrazole. J. Pharmacol. Exp. Therapeut. 237:1986;1012-1019.
44. Tanner A.R., Bantock I., Hinks L., Lloyd B., Turner N.R., Wright R. Depressed selenium and vitamin E levels in an alcoholic population Possible relationship to hepatic injury through increased lipid peroxidation . Dig. Dis. Sci. 31:1986;1307-1312.
45. Bjorneboe G.E., Bjorneboe A., Hagen B.F., Morland J., Drevon C.A. Acute and chronic effects of ethanol on secretion of alpha-tocopherol from primary cultures of rat hepatocytes. Biochim. Biophys. Acta. 918:1987;236-241.
46. Hirano T., Kaplowitz N., Tsukamoto H., Kamimura S., Fernandez-Checa J.C. Hepatic mitochondrial glutathione depletion and progression of experimental alcoholic liver disease in rats. Hepatology. 16:1992;1423-1427.
47. Stoyanovsky D.A., Wu D., Cederbaum A.I. Interaction of 1-hydroxylethyl radical with glutathione, ascorbic acid and α-tocopherol. Free Radic. Biol. Med. 26:1998;132-138.