Spin Trapping of Radical Species Involved in the Propagation of Lipid Peroxidation

  • Gerald M. Rosen
  • Elmer J. Rauckman
  • Eli Finkelstein


Lipid peroxidation is a naturally occurring process involving the generation of free radicals mainly derived from the polyunsaturated fatty acids that are incorporated into the phosphoglycerides of membranes. The peroxidative process has been shown to be a radical chain reactive sequence which has separate initiation, propagation and termination steps.1 Initiation is thought to occur either by a radical addition to a double bond or by abstraction of an allylic hydrogen by a reactive radical. In either case, generation of an appropriate chain initiating radical must preceed the propagation reactions.


Electron Spin Resonance Carbon Tetrachloride Spin Trap Cumene Hydroperoxide Spin Trapping 
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  1. 1.
    J.F. Mead, Free radical mechanisms of lipid damage and consequences for cellular membranes, in: “Free Radicals in Biology”, W.A. Pryor, ed., Vol. I, Academic Press, New York, pp. 51 (1976).Google Scholar
  2. 2.
    E.D. Wills, Lipid peroxidation formation in microsomes, general considerations, Biochem. J. 113: 315 (1969).Google Scholar
  3. 3.
    P. Hochstein and L. Ernsters Evidence for the involvement of iron in the ADP-activated peroxidation of lipids in microsomes and mitochondria, Biochem. Biophys. Res. Commun. 14: 323 (1963).CrossRefGoogle Scholar
  4. 4.
    B.A. Svingen, F.O. O’Neal and S.D. Aust, The role of superoxide and singlet oxygen in lipid peroxidation, Photochem. Photobiol. 28: 803 (1978).CrossRefGoogle Scholar
  5. 5.
    M.M. King, E.K. Lai and P.B. McCay, Singlet oxygen production associated with enzyme-catalyzed lipid peroxidation in liver microsomes, J. Biol. Chem. 250: 6496 (1975).Google Scholar
  6. 6.
    B.A. Svingen, J.A. Buege, F.O. O’Neal and S.D. Aust, The mechanism of NADPH-dependent lipid peroxidation, the propagation of lipid peroxidation, J. Biol. Chem. 254: 5892 (1979).Google Scholar
  7. 7.
    R.O. Recknagel and E.A. Glende, Jr., Carbon tetrachloride hepatoxicity: an example of lethal clevage, CRC Crit. Res. Toxicol. 2: 263 (1973).CrossRefGoogle Scholar
  8. 8.
    G. Sipes, G. Krishna and J.R. Gillette, Bioactivation of carbon tetrachloride, chloroform and bromotrichloromethane: role of cytochrome P-450, Life Sci. 20: 1541 (1977).CrossRefGoogle Scholar
  9. 9.
    J.S.L. Fowler, Carbon tetrachloride metabolism in the rabbit, Brit. J. Pharmacol. 37: 733 (1969).CrossRefGoogle Scholar
  10. 10.
    N.E. Sladik and G.J. Mannering, Induction of drug metabolism II. Qualitative differences in the microsomal N-demethylating systems stimulated by polycyclic hydrocarbons and by phenobarbital, Mol. Pharmacol. 5: 186 (1969).Google Scholar
  11. 11.
    L. Pauling, “The Nature of the Chemical Bond,” Cornell University Press, N.Y., pp. 83 (1960).Google Scholar
  12. 12.
    E. Burdino, E. Gravela, G. Ugazio, V. Vannine and A. Calligaro, Initiation of free radical reactions and hepatotoxicity in rats poisoned with carbon tetrachloride or bromotrichloromethane, Agents Actions 3: 244 (1973).CrossRefGoogle Scholar
  13. 13.
    A. Calligero and V. Vannini, Electron spin resonance study of homolytic cleavage of carbon tetrachloride in rat liver: trichloromethyl free radicals, Pharmacol. Res. Commun. 7: 323 (1975).CrossRefGoogle Scholar
  14. 14.
    K.M. Saucier, Reply to: electron spin resonance study of homolytic cleavage of carbon tetrachloride in rat liver: trichloromethyl free radicals, Pharmacol. Res. Commun. 8: 424 (1976).Google Scholar
  15. 15.
    R.P. Mason, Free radical metabolites of foreign compounds and their toxicological significance, in: “Reviews in Biochemical Toxicology,” E. Hodgson, J.R. Bend and R.M. Philpot, eds., Elsevier/North Holland, New York, pp. 151, (1979).Google Scholar
  16. 16.
    A. Ingall, K.A.K. Lott, T.F. Slater, S. Finch and A. Stier, Metabolic activation of carbon tetrachloride to a free radical product: studies using a spin trap, Biochem. Soc. Trans. 6: 962 (1978).Google Scholar
  17. 17.
    J.L. Poyer, R.A. Floyd; P.B. McCay, E.G. Janzen and E.R. Davis, Spin trapping of the trichloromethyl radical produced during enzymic NADPH oxidation in the presence of carbon tetrachloride or bromotrichloromethane, Biochim. Biophys. Acta 539: 402 (1978).CrossRefGoogle Scholar
  18. 18.
    B. Kalyanaraman, R.P. Mason, E. Perez-Reyes, C.F. Chignell, C.R. Wolff and R.M. Philpot, Characterization of the free radical formed in aerobic microsomal incubations containing carbon tetrachloride, Biochem. Biophys. Res. Commun. 89: 1065 (1979).CrossRefGoogle Scholar
  19. 19.
    E.K. Lai, P.B. McCay, T. Noguchi and K.L. Fong, In vivo spin trapping of trichloromethyl radicals formed from CC14, Biochem. Pharmacol. 28: 2231 (1979).Google Scholar
  20. 20.
    E. Finkelstein, G.M. Rosen and E.J. Rauckman, Spin trapping of superoxide and hydroxyl radical: practical aspects, Arch. Biochem. Biophys. 200: in press (1980).Google Scholar
  21. 21.
    G.M. Rosen and E.J. Rauckman, Spin trapping of the primary radical involved in the activation of the carcinogen, Nhydroxy-2-acetylaminofluorene by cumene hydroperoxide hematin, Mol. Pharmacol. 17: in press (1980).Google Scholar
  22. 22.
    E. Finkelstein, G.M. Rosen, E.J. Rauckman and J. Paxton, Spin trapping of superoxide, Mol. Pharmacol. 16: 676 (1979).Google Scholar
  23. 23.
    E.J. Rauckman, G.M. Rosen, B.B. Kitchell and J.A. Moylan, Oxidation of hydroxylamines to nitroxides by mixed function amine oxidase, in: “Biological Oxidation of Nitrogen,” J.W. Gorrod, ed., Elsevier/North Holland, Amsterdam, pp. 484 (1978).Google Scholar
  24. 24.
    B. Halliwell, Superoxide dependent formation of hydroxyl radicals in the presence of iron chelates, FEBS. Lett. 92: 321 (1978).CrossRefGoogle Scholar
  25. 25.
    J.J.M.C. DeGroot, G.J. Garssen, J.F.G. Vliegenthart and J. Boldingh, The detection of linoleic acid radicals in the anaerobic reaction of lipoxygenase, Biochim. Biophys. Acta. 326: 279 (1973).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1980

Authors and Affiliations

  • Gerald M. Rosen
    • 1
  • Elmer J. Rauckman
    • 1
  • Eli Finkelstein
    • 1
  1. 1.Departments of Pharmacology and SurgeryDuke University Medical CenterDurhamUSA

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