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Richard O. Recknagel, Eric A. Glende
10.1002/cphy.cp090138
Source: Supplement 26: Handbook of Physiology, Reactions to Environmental Agents
Originally published: 1977
Published online: January 2011
Full Article on Wiley Online Library
The sections in this article are:
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Figure 1. Peroxidation of a polyenoic long‐chain fatty acid. |
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Figure 2. Hypothetical destruction of cytochrome P‐450 through direct attack by toxic metabolites of CCl4. |
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Figure 3. Hypothetical destruction of cytochrome P‐450 through indirect attack by toxic products of lipid peroxidation. |
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Figure 4. Cytochrome P‐450 and in vitro metabolism of CCl4. Left panel: Note no loss of cytochrome P‐450 during anaerobic conversion of CCl4 to CHCl3, and note also the absence of lipid peroxidation. Right panel: Note substantial loss of cytochrome P‐450 when lipid peroxidation occurs. |
| References | |
| 1. | Aaes‐Jorgensen, E. Autoxidation of fatty compounds in living tissue, biological antioxidants. In: Autoxidation and Antioxidants, edited by W. O. Lundberg. New York: Wiley, 1962, vol. ii, p. 1045‐1093. |
| 2. | Alfin‐Slater, R. B., and R. S. Morris. Vitamin E and lipid metabolism. Adv. Lipid Res. 1: 183–210, 1963. |
| 3. | Arstila, A. U., M. A. Smith, and B. F. Trump. Microsomal lipid peroxidation: morphological characterization. Science 175: 530–533, 1972. |
| 4. | Ashworth, C. T., F. J. Luibel, E. Sanders, and N. Arnold. Hepatic cell degeneration: correlation of fine structure with chemical and histochemical changes in hepatic cell injury produced by carbon tetrachloride in rats. Arch. Pathol. 75: 212–225, 1963. |
| 5. | Aust, S. D., D. L. Roerig, and T. C. Pederson. Evidence for superoxide generation by NADPH‐cytochrome reductase of rat liver microsomes. Biochem. Biophys. Res. Commun. 47: 1133–1137, 1972. |
| 6. | Bacq, Z. M. Chemical Protection Against Ionizing Radiation. Springfield, III.: Thomas, 1965. (Am. Lecture in Living Chemistry Ser.). |
| 7. | Bartley, W., Lipids of intracellular organelles. In: Metabolism and Physiological Significance of Lipids, edited by R. M. C. Dawson and D. N. Rhodes. New York: Wiley, 1964, p. 369‐381. |
| 8. | Bassi, M. Electron microscopy of rat liver after carbon tetrachloride poisoning. Exptl. Cell Res. 20: 313–323, 1960. |
| 9. | Bateman, L. Olefin oxidation. Quart. Rev., London 8: 147‐167, 1954. |
| 10. | Bunyan, J., J. Green, E. E. Edwin, and A. T. Diplock. Studies on vitamin E. 5. Lipid peroxidation in dialuric acid‐induced hemolysis of vitamin E‐deficient erythrocytes. Biochem. J. 76: 47–51, 1960. |
| 11. | Burdino, E., E. Gravela, G. Ugazio, V. Vannini, and A. Calligaro. Initiation of free radical reactions and hepatotoxicity in rats poisoned with carbon tetrachloride or bromotrichloromethane. Agents and Actions 4: 244–253, 1973. |
| 12. | Butler, T. C. Reduction of carbon tetrachloride in vivo and reduction of carbon tetrachloride and chloroform in vitro by tissues and tissue homogenates. J. Pharmacol. Exptl. Therap. 134: 311–319, 1961. |
| 13. | Carlson, G. P. Protective effect of methylmercury hydroxide on carbon tetrachloride induced hepatotoxicity. Federation Proc. 33: 228, 1974. |
| 14. | Castro, J. A., M. I. Diaz Gomez, E. C. deFerregra, C. R. deCastro, N. D'Acosta, and O. M. DeFenos. Carbon tetrachloride effect on rat liver and adrenals related to their mixed function oxygenase content. Biochem. Biophys. Res. Commun. 47: 315–321, 1972. |
| 15. | Castro, J. A., H. A. Sasame, H. Sussman, and J. R. Gillette. Diverse effects of SKF‐525A and anti‐oxidants on carbon tetrachloride induced changes in liver microsomal P450 content and ethylmorphine metabolism. Life Sci., Part 1 7: 129–136, 1968. |
| 16. | Cawthorne, M. A., J. Bunyan, M. V. Sennitt, and J. Green. Vitamin E and hepatotoxic agents. 3. Vitamin E, synthetic antioxidants and carbon tetrachloride toxicity in the rat. Brit. J. Nutr. 24: 357–384, 1970. |
| 17. | Chaplin, M. N., and G. J. Mannering. Role of phospholipids in the hepatic microsomal drug‐metabolizing system. Mol. Pharmacol. 6: 631–640, 1970. |
| 18. | Christophersen, B. O. Oxidation of reduced glutathione by subcellular fractions of rat liver. Biochem. J. 100: 95–101, 1966. |
| 19. | Christophersen, B. O. Formation of monohydroxy‐polyenic fatty acids from lipid peroxides by a glutathione peroxidase. Biochim. Biophys. Acta 164: 35–46, 1968. |
| 20. | Christophersen, B. O. The inhibitory effect of reduced glutathione on the lipid peroxidation of the microsomal fraction and mitochondria. Biochem. J. 106: 515–522, 1968. |
| 21. | Cignoli, E. V., and J. A. Castro. Effect of inhibitors of drug metabolizing enzymes on carbon tetrachloride hepatotoxicity. Toxicol. Appl. Pharmacol. 18: 625–637, 1971. |
| 22. | Cignoli, E. V., and J. A. Castro. Lipid peroxidation, necrosis and the in vivo depression of liver glucose‐6‐phosphatase by carbon tetrachloride. Exptl. Mol. Pathol. 14: 43–56, 1971. |
| 23. | Clark, J. M., and C. J. Lambertsen. Pulmonary oxygen toxicity: a review. Pharmacol. Rev. 23: 37–133, 1971. |
| 24. | Cleveland, P. D., and E. A. Smuckler. Effect of CCl4, dimethylnitrosamine and thioacetamide on hepatic DPNH and TPNH cytochrome c reductase. Proc. Soc. Exptl. Biol. Med. 120: 808–810, 1965. |
| 25. | Commoner, B., J. J. Heise, B. B. Lippincott, R. E. Norberg, J. V. Passomeau, and J. Townsend. Biological activity of free radicals. Science 126: 57–63, 1957. |
| 26. | Comporti, M., and G. A. Rita. Effect of some cations on the in vitro inactivation by heat and by CCl4 of microsomal glucose‐6‐phosphatase. Ital. J. Biochem. 15: 178–188, 1966. |
| 27. | Dahle, L. K., E. G. Hill, and R. T. Holman. The thiobarbituric acid reaction and the autoxidations of polyunsaturated fatty acid methyl esters. Arch. Biochem. Biophys. 98: 253–261, 1962. |
| 28. | Dambrauskas, T., and H. H. Cornish. Effect of pretreatment of rats with carbon tetrachloride on tolerance development. Toxicol. Appl. Pharmacol. 17: 83–97, 1970. |
| 29. | Davies, H. C., and R. E. Davies. Biochemical aspects of oxygen poisoning. In: Handbook of Physiology. Respiration, edited by W. O. Fenn and H. Rahn. Washington, D.C.: Am. Physiol. Soc., 1965, sect. 3, vol. ii, chapt. 40, p. 1047‐1058. |
| 30. | DeMatteis, F., and R. G. Sparks. Iron‐dependent loss of liver cytochrome P‐450 heme in vivo and in vitro. FEBS Letters 29: 141–144, 1973. |
| 31. | Desai, I. D., P. L. Sawant, and A. L. Tappel. Peroxidative and radiation damage to isolated lysosomes. Biochim. Biophys. Acta 86: 277–285, 1964. |
| 32. | Dodge, J. T., G. Cohen, H. J. Kayden, and G. B. Phillips. Peroxidative hemolysis of red blood cells from patients with abetalipoproteinemia (acanthocytosis). J. Clin. Invest. 46: 357–368, 1967. |
| 33. | Duling, B. R., and R. M. Berne. Longitudinal gradients in periarteriolar oxygen tension: A possible mechanism for participation of oxygen in local regulation of blood flow. Circulation Res. 27: 669–678, 1970. |
| 34. | Duterea, S. M., W. L. Byrne, and M. C. Ganoza. Studies on the phospholipid requirement of glucose‐6‐phosphatase. J. Biol. Chem. 243: 2216–2228, 1968. |
| 35. | Fee, J. A., and H. D. Teitelbaum. Evidence that superoxide dismutase plays a role in protecting red cells against peroxidative hemolysis. Biochem. Biophys. Res. Commun. 49: 150–158, 1972. |
| 36. | Findlay, G. M., H. H. Draper, and J. G. Bergan. Metabolism of 1‐ 14C‐methyl linoleate hydroperoxide in the rabbit. Lipids 5: 970–975, 1970. |
| 37. | Gerschman, R., The biological effects of increased oxygen tension. In: Man's Dependence on the Earthly Atmosphere, edited by K. E. Schaefer. New York: Macmillan, 1958, p. 171. |
| 38. | Gerschman, R., Biological effects of oxygen. In: Oxygen in the Animal Organism, edited by F. Dickens and E. Neil. New York: Macmillan, 1964, p. 475‐494. |
| 39. | Gerschman, R., D. L. Gilbert, S. W. Nye, P. Dwyer, and W. O. Fenn. Oxygen poisoning and X‐irradiation: a mechanism in common. Science 119: 623–626, 1954. |
| 40. | Ghoshal, A. K., and R. O. Recknagel. On the mechanism of carbon tetrachloride hepatotoxicity: Co‐incidence of loss of glucose‐6‐phosphatase activity with peroxidation of microsomal lipid. Life Sci. 4: 2195–2209, 1965. |
| 41. | Glende, E. A., Jr.. Carbon tetrachloride‐induced protection against carbon tetrachloride toxicity: Role of the liver microsomal drug‐metabolizing system. Biochem. Pharmacol. 21: 1697–1702, 1972. |
| 42. | Glende, E. A., Jr.. On the mechanism of carbon tetrachloride toxicity — coincidence of loss of drug metabolizing activity with peroxidation of microsomal lipid. Biochem. Pharmacol. 21: 2131–2138, 1972. |
| 43. | Glende, E. A., Jr., and R. O. Recknagel. Biochemical basis for the in vitro pro‐oxidant action of carbon tetrachloride. Exptl. Mol. Pathol. 11: 172–185, 1969. |
| 44. | Glende, E. A., Jr., and R. O. Recknagel. Microsomal electron transport and in vitro CCl4‐induced lipoperoxidation. Federation Proc. 29: 755, 1970. |
| 45. | Glende, E. A., Jr., and R. O. Recknagel. The relationship between liver microsomal carbon tetrachloride metabolism, lipid peroxidation and cytochrome P‐450 content. Federation Proc. 33: 219, 1974. |
| 46. | Goldstein, B. D., R. D. Buckley, R. Cardenas, and O. J. Balchum. Ozone and vitamin E. Science 169: 605–606, 1970. |
| 47. | Goldstein, B. D., C. Lodi, C. Collinson, and O. J. Balchum. Ozone and lipid peroxidation. Arch. Environ. Health 18: 631–635, 1969. |
| 48. | Graham, A. B., and G. C. Wood. The phospholipid‐dependence of UDP‐glucuronyltransferase. Biochem. Biophys. Res. Commun. 37: 567–575, 1969. |
| 49. | Gram, T. E., and J. R. Fouts. Effect of α‐tocopherol upon lipid peroxidation and drug metabolism in hepatic microsomes. Arch. Biochem. Biophys. 114: 331–335, 1966. |
| 50. | Greene, F. E., B. Strippe, and J. R. Gillette. The effect of carbon tetrachloride on heme components and ethylmor phine metabolism in rat liver microsomes. Biochem. Pharmacol. 18: 1531–1533, 1969. |
| 51. | Green, J., Vitamin E and the biological antioxidant theory. In: Vitamin E and Its Role in Cellular Metabolism, edited by P. P. Nair and H. J. Kayden. New York: NY Acad. Sci., 1972, p. 29‐44. (Annals NY Acad. Sci., vol. 203.). |
| 52. | Green, J., and J. Bunyan. Vitamin E and the biological antioxidant theory. Nutr. Abstr. Rev. 39: 321–345, 1969. |
| 53. | Green, J., J. Bunyan, M. A. Cawthorne, and A. T. Diplock. Vitamin E and hepatotoxic agents. 1. Carbon tetrachloride and lipid peroxidation in the rat. Brit. J. Nutr. 23: 297–307, 1969. |
| 54. | Gross, S., and D. K. Melhorn. Vitamin E, red cell lipids and red cell stability in prematurity. In: Vitamin E and Its Role in Cellular Metabolism, edited by P. P. Nair and H. J. Kayden. New York: NY Acad. Sci., 1972, p. 141‐162. (Annals NY Acad. Sci., vol. 203.). |
| 55. | Haugaard, N. Cellular mechanisms of oxygen toxicity. Physiol. Rev. 48: 311–373, 1968. |
| 56. | Haurowitz, F., and P. Schwerin. Hämin‐Katalysen in Grenzflächen‐Film zwischen Wasser und Ölphase. Enzymologia 9: 193–197, 1940. |
| 57. | Haurowitz, F., P. Schwerin, and M. Jensen. Destruction of hemin and hemoglobin by the action of unsaturated fatty acids and oxygen. J. Biol. Chem. 140: 353–359, 1951. |
| 58. | Hayaishi, O. (editor)., Oxygenases. New York: Academic Press, 1962. |
| 59. | Hochstein, P., and L. Ernster. ADP‐activated lipid peroxidation coupled to the TPNH oxidase system of microsomes. Biochem. Biophys. Res. Commun. 12: 388–394, 1963. |
| 60. | Hochstein, P., and L. Ernster. Microsomal peroxidation of lipids and its possible role in cellular injury. In: Cellular Injury, edited by A. V. S. deReuck and J. Knight. Boston: Little, Brown, 1964, p. 123‐134. (Ciba Foundation Symposium.). |
| 61. | Hoffsten, P. E., F. E. Hunter, Jr., J. M. Gebicki, and J. Weinstein. Formation of “lipid peroxide” under conditions which lead to swelling and lysis of rat liver mitochondria. Biochem. Biophys. Res. Commun. 7: 276–280, 1962. |
| 62. | Högberg, J., A. Bergstrand, and S. V. Jakobsson. Lipid peroxidation of rat liver microsomes: Its effect on the microsomal membrane and some membrane‐bound microsomal enzymes. European J. Biochem. 37: 51–59, 1973. |
| 63. | Holman, R. T. Autoxidation of fats and related substances. Progr. Chem. Fats Lipids 2: 51, 1954. |
| 64. | Horgan, V. J., J. S. L. Philpot, B. W. Porter, and D. B. Roodyn. Toxicity of autoxidized squalene and linoleic acid, or of simpler peroxides, in relation to toxicity of radiation. Biochem. J. 67: 551–558, 1957. |
| 65. | Horwitt, M. K. Role of vitamin E, selenium, and polyunsaturated fatty acids in clinical and experimental muscle disease. Federation Proc. 24: 68–72, 1965. |
| 66. | Hrycay, E. G., and P. J. O'Brien. Cytochrome P‐450 as a microsomal peroxidase utilizing a lipid peroxide substrate. Arch. Biochem. Biophys. 147: 14–27, 1971. |
| 67. | Hrycay, E. G., and P. J. O'Brien. The peroxidase nature of cytochrome P‐420 utilizing a lipid peroxide substrate. Arch. Biochem. Biophys. 147: 28–35, 1971. |
| 68. | Hunter, F. E., Jr., A. Scott, P. E. Hoffsten, J. M. Gebicki, and A. Schneider. Studies on the mechanism of swelling, lysis and disintegration of isolated liver mitochondria exposed to mixtures of oxidized and reduced glutathione. J. Biol. Chem. 239: 614–621, 1964. |
| 69. | Hunter, F. E., Jr., A. Scott, P. E. Hoffsten, F. Guerra, J. Weinstein, A. Schneider, B. Schultz, J. Fink, L. Ford, and E. Smith. Studies on the mechanism of ascorbate‐induced swelling and lysis of isolated liver mitochondria. J. Biol. Chem. 239: 604–613, 1964. |
| 70. | Hunter, F. E., Jr., A. Scott, J. Weinstein, and A. Schneider. Effects of phosphate, arsenate, and other substances on swelling and lipid peroxide formation when mitochondria are treated with oxidized and reduced glutathione. J. Biol. Chem. 239: 622–630, 1964. |
| 71. | Jacobson, M., W. Levin, A. Y. H. Lu, A. H. Conney, and R. Kuntzman. The rate of pentobarbital and acetanilide metabolism by liver microsomes: A function of lipid peroxidation and degradation of cytochrome P‐450 heme. Drug. Metab. Disposition 1: 766–777, 1973. |
| 72. | Jerrett, S. A., D. Jefferson, and C. E. Mengel. Seizures, H2O2 formation and lipid peroxides in brain during exposure to oxygen under high pressure. Aerospace Med. 44: 40–44, 1973. |
| 73. | Kamataki, T., and H. Kitagawa. Effects of lipid peroxidation on activities of drug‐metabolizing enzymes in liver microsomes of rats. Biochem. Pharmacol. 22: 3199–3207, 1973. |
| 74. | Koch, R. R., E. A. Glende, Jr., and R. O. Recknagel. Hepatotoxicity of bromotrichloromethane. Gastroenterology 65: 553, 1973. |
| 75. | Koch, R. R., E. A. Glende, Jr., and R. O. Recknagel. Hepatotoxicity of bromotrichloromethane: Bond dissociation energy and lipoperoxidation. Biochem. Pharmacol. 23: 2907‐2915, 1974. |
| 76. | Kokatnur, M. G., J. G. Bergan, and H. H. Draper. Observations on the decomposition of hemin by fatty acid hydroperoxides. Proc. Soc. Exptl. Biol. Med. 123: 314–317, 1966. |
| 77. | Leach, S. J. The mechanism of enzymic oxidoreduction. Advan. Enzymol. 15: 1–47, 1954. |
| 78. | Levin, W., M. Jacobson, and R. Kuntzman. Incorporation of radioactive‐d‐aminolevulinic acid into microsomal cytochrome P450: Selective breakdown of the hemoprotein by allylisopropylacetamide and carbon tetrachloride. Arch. Biochem. Biophys. 148: 262–269, 1972. |
| 79. | Levin, W., A. Y. H. Lu, M. Jacobson, R. Kuntzman, J. L. Poyer, and P. B. McCay. Lipid peroxidation and the degradation of cytochrome P‐450 heme. Arch. Biochem. Biophys. 158: 842–852, 1973. |
| 80. | Lucy, J. A., Functional and structural aspects of biological membranes: A suggested structural role for vitamin E in the control of membrane permeability and stability. In: Vitamin E and Its Role in Cellular Metabolism, edited by P. P. Nair and N. J. Kayden. New York: NY Acad. Sci., 1972, p. 4‐11. (Annals NY Acad. Sci., vol. 203.). |
| 81. | Lumper, L., Z. Aubrzycki, and H. Standinger. Inacktivierung mikrosomaler Enzyme durch Phospholipase D. Hoppe‐Seyler's Z. Physiol. Chem. 350: 163, 1969. |
| 82. | Lundberg, W. O. (editor)., Autoxidation and Antioxidants. New York: Wiley, 1961‐1962, 2 vols. |
| 83. | Mageli, O. L., and C. S. Sheppard. Organic peroxides and peroxy compounds — general description. In: Organic Peroxides, edited by D. Swern. New York: Wiley, 1970, vol. 1, p. 1‐104. |
| 84. | Marks, J. Critical appraisal of the therapeutic value of α‐tocopherol. Vitamins Hormones 20: 573–598, 1962. |
| 85. | Martonosi, A., J. Donley, and R. A. Halpin. Sarcoplasmic reticulum. III. The role of phospholipids in the adenosine triphosphatase activity and Ca++ transport. J. Biol. Chem. 243: 61–70, 1968. |
| 86. | May, H. E., and P. B. McCay. Reduced triphosphopyridine nucleotide oxidase‐catalyzed alterations of membrane phospholipids. I. Nature of the lipid alterations. J. Biol. Chem. 243: 2288–2295, 1968. |
| 87. | May, H. E., and P. B. McCay. Reduced triphosphopyridine nucleotide oxidase‐catalyzed alterations of membrane lipids. II. Enzymic properties and stoichiometry. J. Biol. Chem. 243: 2296–2305, 1968. |
| 88. | McCord, J. M., and I. Fridovich. Superoxide dismutase: an enzymic function for erythrocuprein. J. Biol. Chem. 244: 6049–6055, 1969. |
| 89. | McCord, J. M., B. B. Keele, Jr., and I. Fridovich. An enzyme‐based theory of obligate anaerobiosis. Proc. Natl. Acad. Sci. US 68: 1024–1027, 1971. |
| 90. | McLean, A. E. M. The effect of diet and vitamin E on liver injury due to carbon tetrachloride. Brit. J. Exptl. Pathol. 48: 632–636, 1967. |
| 91. | McLean, A. E. M. Effect of hexane and carbon tetrachloride on microsomal cytochrome (P450). Biochem. Pharmacol. 16: 2030–2033, 1967. |
| 92. | McMillan, G. R., and J. G. Calvert. Gas phase photo‐oxidation. Oxidation Combust. Rev. 1: 84–135, 1965. |
| 93. | Mengel, C. E., and H. E. Kann, Jr.. Effect of in vivo hyperoxia on erythrocytes. III. In vivo peroxidation of erythrocyte lipid. J. Clin. Invest. 45: 1150–1157, 1966. |
| 94. | Mengel, C. E., H. E. Kann, Jr., and W. D. Meriwether. Studies of paroxysmal nocturnal hemoglobinuria erythrocytes. Increased lysis and lipid peroxide formation by hydrogen peroxide. J. Clin. Invest. 46: 1715–1723, 1967. |
| 95. | Menzel, D. B. Toxicity of ozone, oxygen, and radiation. Ann. Rev. Pharmacol. 10: 379–394, 1970. |
| 96. | Menzel, D. B. (editor)., Symposium on pollution and lung biochemistry. Arch. Internal Med. 128: 48–117, 1971. |
| 97. | Michaelis, L. Some aspects of reversible step reactions. Advan. Enzymol. 9: 1–23, 1949. |
| 98. | Mickel, H. S., and J. Horbar. The effect of peroxidized arachidonic acid upon human platelet aggregation. Lipids 9: 68–71, 1974. |
| 99. | Nair, P. P., and H. J. Kayden (editors)., Vitamin E and Its Role in Cellular Metabolism. New York: NY Acad. Sci., 1972, p. 1‐247. (Annals NY Acad. Sci., vol. 203.). |
| 100. | Nitowsky, H. M., K. S. Hsu, and H. H. Gordon. Vitamin E requirements of human infants. Vitamins Hormones 20: 559–571, 1962. |
| 101. | Oberling, C., and C. Rouiller. Les effets de l'intoxication aiguë au tetrachlorine de carbone sur le foie du rat. Ann. Anat. Pathol. 1: 401–427, 1956. |
| 102. | O'Brien, P. J. Intracellular mechanisms for the decomposition of a lipid peroxide by metal ions, heme compounds, and nucleophiles. Can. J. Biochem. 47: 485–492, 1969. |
| 103. | Olcott, H. S., and A. Doleo. Toxicity of fatty acid ester hydroperoxides. Proc. Soc. Exptl. Biol. Med. 114: 820–822, 1963. |
| 104. | Orrenius, S., G. Dallner, and L. Ernster. Inhibition of the TPNH‐linked lipid peroxidation of liver microsomes by drugs undergoing oxidative demethylation. Biochem. Biophys. Res. Commun. 14: 329–334, 1964. |
| 105. | Pauling, L. The Nature of the Chemical Bond and the Structure of Molecules and Crystals (3rd ed.). Ithaca, N.Y.: Cornell Univ. Press, 1960. |
| 106. | Pederson, T. C., and S. D. Aust. NADPH‐dependent lipid peroxidation catalyzed by purified NADPH‐cytochrome c reductase from rat liver microsomes. Biochem. Biophys. Res. Commun. 48: 789–795, 1972. |
| 107. | Pfeifer, P. M., and P. B. McCay. Reduced triphosphopyridine nucleotide oxidase‐catalyzed alterations of membrane phospholipids. V. Use of erythrocytes to demonstrate enzyme‐dependent production of a component with the properties of a free radical. J. Biol. Chem. 246: 6401–6408, 1971. |
| 108. | Pryor, W. A. Free radical pathology. Chem. Eng. News 49: 34–51, 1971. |
| 109. | Rao, K. S., and R. O. Recknagel. Early incorporation of carbon‐labeled carbon tetrachloride into rat liver particulate lipids and proteins. Exptl. Mol. Pathol. 10: 219–228, 1969. |
| 110. | Recknagel, R. O. Carbon tetrachloride hepatoxicity. Pharmacol. Rev. 19: 145–208, 1967. |
| 111. | Recknagel, R. O., and A. K. Ghoshal. Lipoperoxidation as a vector in carbon tetrachloride hepatoxicity. Lab. Invest. 15: 132–148, 1966. |
| 112. | Recknagel, R. O., and A. K. Ghoshal. Quantitative estimation of peroxidative degeneration of rat liver microsomal and mitochondrial lipids after carbon tetrachloride poisoning. Exptl. Mol. Pathol. 5: 413–426, 1966. |
| 113. | Recknagel, R. O., and A. K. Ghoshal. On the chemical reactivity of carbon tetrachloride as the basis of its toxicological action. Progr. Biochem. Pharmacol. 3: 450–461, 1967. |
| 114. | Recknagel, R. O., and E. A. Glende, Jr.. Carbon tetrachloride hepatotoxicity: An example of lethal cleavage. C.R.C. Critical Rev. in Toxicology 2: 263–297, 1973. |
| 115. | Recknagel, R. O., and E. A. Glende, Jr., Lipid peroxidation in acute carbon tetrachloride liver injury. In: Intermediary Metabolism of the Liver, edited by H. Brown and D. F. Hardwick. Springfield, III.: Thomas, 1973, p. 23‐57. |
| 116. | Recknagel, R. O., E. A. Glende, Jr., G. Ugazio, R. R. Koch, and S. Srinivasan. New data in support of the lipoperoxidation theory for carbon tetrachloride liver injury. Israel J. Med. Sci. 4: 301–311, 1974. |
| 117. | Recknagel, R. O., and B. Lombardi. Studies of biochemical changes in subcellular particles of rat liver and their relationship to a new hypothesis regarding the pathogenesis of carbon tetrachloride fat accumulation. J. Biol. Chem. 236: 564–569, 1961. |
| 118. | Reiner, O., S. Athanassopoulos, K. H. Hellmer, R. E. Murray, and H. Uehleke. Bildung von Chloroform aus Tetrachlorkolenstoff in Lebermikrosomen, Lipidperoxidation und Zerstorüng von Cytochrom P‐450. Arch. Toxikol. 29: 219–233, 1972. |
| 119. | Reiner, O., and H. Uehleke. The effect of CCl4 on lipid peroxidation and cytochrome P450 in the endoplasmic reticulum. Naunyn‐Schmiedebergs Arch. Pharmacol. Suppl. 270: R111, 1970. |
| 120. | Reiner, O., and H. Uehleke. Bindung von Tetrachlorkoh‐lenstuff an reduziertes mikrosomales Cytochrom P‐450 und an Häm. Hoppe‐Seyler's Z. Physiol. Chem. 352: 1048–1052, 1971. |
| 121. | Robinson, J. D. Structural changes in microsomal suspensions. III. Formation of lipid peroxides. Arch. Biochem. Biophys. 112: 170–179, 1965. |
| 122. | Robinson, J. D. Interaction between protein sulfhydryl groups and lipid double bonds in biological membranes. Nature 212: 199–200, 1966. |
| 123. | Robinson, M. E. Hemoglobin and methemoglobin as oxidative catalysts. Biochem. J. 18: 255–264, 1924. |
| 124. | Roth, N. G., and H. O. Halvorson. The effect of oxidative rancidity in unsaturated fatty acids on germination of bacterial spores. J. Bacteriol. 63: 429–435, 1952. |
| 125. | Sasame, H. A., J. A. Castro, and J. R. Gillette. Studies on the destruction of liver microsomal cytochrome P‐450 by carbon tetrachloride administration. Biochem. Pharmacol. 17: 1759–1768, 1968. |
| 126. | Schacter, B. A., H. S. Marver, and U. A. Meyer. Hemoprotein catabolism during stimulation of microsomal lipid peroxidation. Biochim. Biophys. Acta 279: 221–227, 1972. |
| 127. | Schacter, B. A., H. S. Marver, and U. A. Meyer. Heme and hemoprotein catabolism during stimulation of microsomal lipid peroxidation. Drug. Metab. Disposition 1: 286–290, 1973. |
| 128. | Schenkman, J. B., H. Remmer, and R. W. Estabrook. Spectral studies of drug interaction with hepatic microsomal cytochrome. Mol. Pharmacol. 3: 113–123, 1967. |
| 129. | Schultz, H. W., E. A. Day, and R. O. Sinnhuber (editors)., Symposium on Foods: Lipids and Their Oxidation. Westport, Conn: Avi, 1962. |
| 130. | Schwarz, K., The cellular mechanisms of vitamin E action: Direct and indirect effects of α‐tocopherol on mitochondrial respiration. In: Vitamin E and Its Role in Cellular Metabolism, edited by P. P. Nair and H. J. Kayden. New York: NY Acad. Sci. 1972, p. 45‐52. (Annals NY Acad. Sci. vol. 203.). |
| 131. | Seawright, A. A., and A. E. M. McLean. The effect of diet on carbon tetrachloride metabolism. Biochem. J. 105: 1055–1060, 1967. |
| 132. | Silver, M. J., W. Hoch, J. J. Kocsis, C. M. Ingerman, and J. B. Smith. Arachidonic acid causes sudden death in rabbits. Science 183: 1085–1087, 1974. |
| 133. | Sladek, N. E., 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: 186–199, 1969. |
| 134. | Slater, T. F. Free Radical Mechanisms in Tissue Injury. London: Pion, 1972. |
| 135. | Slater, T. F., and B. C. Sawyer. The stimulatory effects of carbon tetrachloride on peroxidative reactions in rat liver fractions in vitro. Interaction sites in the endoplasmic reticulum. Biochem. J. 123: 815–821, 1971. |
| 136. | Smuckler, E. A., E. Arrhenius, and T. Hultin. Alterations in microsomal electron transport, oxidative N‐demethylation and azo‐dye cleavage in carbon tetrachloride and dimethylnitrosamine‐induced liver injury. Biochem. J. 103: 55–64, 1967. |
| 137. | Smuckler, E. A., O. A. Iseri, and E. P. Benditt. An intracellular defect in protein synthesis induced by carbon tetrachloride. J. Exptl. Med. 116: 55–72, 1962. |
| 138. | Stokinger, H. E. Ozone toxicology. Arch. Environ. Health 10: 719–731, 1965. |
| 139. | Strobel, H. W., A. Y. H. Lu, J. Heidema, and M. J. Coon. Phosphatidylcholine requirement in the enzymatic reduction of hemoprotein P‐450 and in fatty acid, hydrocarbon, and drug hydroxylations. J. Biol. Chem. 245: 4851–4854, 1970. |
| 140. | Tam, B. K., and P. B. McCay. Reduced triphosphopyridine nucleotide oxidase‐catalyzed alterations of membrane phospholipids. III. Transient formation of phospholipid peroxides. J. Biol. Chem. 245: 2295–2300, 1970. |
| 141. | Tappel, A. L., Biocatalysts: Lipoxidase and hematin compounds. In: Autoxidation and Antioxidants, edited by W. O. Lundberg. New York: Wiley, 1961, vol. 1, p. 325‐366. |
| 142. | Tappel, A. L., Vitamin E and selenium as inhibitors in in vivo lipid oxidation. In: Symposium on Foods: Lipids and Their Oxidation, edited by H. W. Schultz, E. A. Day, and R. O. Sinnhuber. Westport, Conn.: Avi, 1962, p. 367‐386. |
| 143. | Tappel, A. L. Vitamin E as the biological lipid antioxidant. Vitamins Hormones 20: 493–510, 1962. |
| 144. | Tappel, A. L. Free‐radical lipid peroxidation damage and its inhibition by vitamin E and selenium. Federation Proc. 24: 73–78, 1965. |
| 145. | Tappel, A. L., Reactions of vitamin E, ubiquinol, and selenoamino acids, and protection of oxidant‐labile enzymes. In: The Fat‐Soluble Vitamins, edited by H. F. DeLuca and J. W. Suttie. Madison: Univ. of Wisconsin Press, 1970, p. 369‐373. |
| 146. | Tappel, A. L., Vitamin E and free radical peroxidation of lipids. In: Vitamin E and Its Role in Cellular Metabolism, edited by P. P. Nair and H. J. Kayden. New York: NY Acad. Sci. 1972, p. 12‐28. (Annals NY Acad. Sci., vol. 203.). |
| 147. | Tappel, A. L., and H. Zalkin. Lipid peroxidation in isolated mitochondria. Arch. Biochem. Biophys. 80: 326–332, 1959. |
| 148. | Taylor, D. W. The effects of vitamin E and methylene blue on the manifestation of oxygen poisoning in the rat. J. Physiol. London 131: 200–206, 1956. |
| 149. | Thomas, H. V., P. K. Mueller, and R. L. Lyman. Lipoperoxidation of lung lipids in rats exposed to nitrogen dioxide. Science 159: 532–534, 1967. |
| 150. | Tsen, C. C., and H. B. Collier. The protective action of tocopherol against hemolysis of rat erythrocytes by dialuric acid. Can. J. Biochem. Physiol. 38: 957–964, 1960. |
| 151. | Uehleke, H., K. H. Hellmer, and S. Tabarelli. Binding of 14CCl4 to microsomal proteins in vitro and formation of CHCl3 by reduced liver microsomes. Xenobiotica 3: 1–11, 1973. |
| 152. | Uehleke, H., F. Schnitger, and K. H. Hellmer. Verhalten verschiedener mikrosomaler Frempstoff‐Oxidationen nach Inaktivierung von Cytochrom P‐450 durch UV‐Bestrahlung oder durch Desoxycholatehandlung. Hoppe‐Seyler's Z. Physiol. Chem. 351: 1475–1484, 1970. |
| 153. | Ugazio, G., R. R. Koch, and R. O. Recknagel. Protection against lethal doses of CCl4 by prior CCl4 administration. Gastroenterology 60: 188, 1971. |
| 154. | Ugazio, G., R. R. Koch, and R. O. Recknagel. Mechanism of protection against carbon tetrachloride by prior carbon tetrachloride administration. Exptl. Mol. Pathol. 16: 281–285, 1972. |
| 155. | Ugazio, G., R. R. Koch, and R. O. Recknagel. Reversibility of liver damage in rats rendered resistant to CCl4 by prior CCl4 administration: Bearing on the lipoperoxidation hypothesis. Exptl. Mol. Pathol. 18: 281–289, 1973. |
| 156. | Vitamin E as a biological antioxidant. Dairy Council Digest 42: 19‐22, 1971. |
| 157. | Whalen, W. J. Intracellular PO2 in heart and skeletal muscle. Physiologist 14: 69–82, 1971. |
| 158. | Wills, E. D. Lipid peroxide formation in microsomes. Relationship of hydroxylation to lipid peroxide formation. Biochem. J. 113: 333–341, 1969. |
| 159. | Wills, E. D. Effects of lipid peroxidation on membranebound enzymes of the endoplasmic reticulum. Biochem. J. 123: 983–991, 1971. |
| 160. | Wills, E. D., and A. E. Wilkinson. Release of enzymes from lyosomes by irradiation and the relation of lipid peroxide formation to enzyme release. Biochlem. J. 99: 657–666, 1966. |
| 161. | Winter, P. M., and G. Smith. The toxicity of oxygen. Anesthesiology 37: 210–241, 1972. |
| 162. | Witting, L. A. Lipid peroxidation in vivo. J. Am. Oil. Chemists Soc. 42: 908–913, 1965. |
| 163. | Witting, L. A., Intermediary metabolism of vitamin E. In: The Biochemistry Assay, and Nutritional Value of Vitamin E. Chicago: Assoc. Vitamin Chem., 1969. |
| 164. | Witting, L. A. Interrelationship of polyunsaturated fatty acids and antioxidants in vivo. Progr. Chem. Fats Lipids 9: 519–553, 1970. |
