Proline Interaction with Trichloromethyl and Tri-Chloromethyl Peroxyl Free Radicals in a Model System: Studies about The Nature of the Reaction Products Formed

References

• Ansari G. A., Moslen M. T., Reynolds E. S. Evidence for in vivo covalent binding of CC13 derived from CC14 to cholesterol of rat liver. Biochem. Pharmacol 1982; 31: 3509–3510
   PubMed Web of Science ®Google Scholar
• Bolarin D. M., Barker K., Fuller G. C. Enzyme markers of collagen synthesis in carbon tetrachloride-induced fibrosis and during colchicine modification of CCl4-induced liver injury. Exp. Mol. Pathol. 1987; 46: 145–152
   PubMed Web of Science ®Google Scholar
• Camps J., Bargallo T., Gimenez A., Alie J., Caballeria J., Pares A., Joven J., Masana L., Rodes J. Relationship between hepatic lipid peroxidation and fibrogenesis in carbon tetrachloride-treated rats: Effects of zinc administration. Clin. Sci. 1992; 83: 695–700
   PubMed Web of Science ®Google Scholar
• Castro de C. R., Bernacchi A. S., Villarruel M. C, Fernandez G., Castro J. A. Carbon tetrachloride activation by highly purified liver mitochondrial preparations. Agents Actions 1984; 15: 664–667
   PubMedGoogle Scholar
• Castro G. D., Díaz Gómez M. I., Castro J. A. Species differences in the interaction between CC14 reactive metabolites and liver DNA and nuclear protein fractions. Carcinogenesis 1989a; 10: 289–294
   PubMed Web of Science ®Google Scholar
• Castro G. D., Díaz Gómez M. I., Castro J. A. Dimethyl-disulfide formation during trichloromethyl radicals attack on methionine. Biochem. Pharmacol. 1989b; 38: 4145–4147
   PubMed Web of Science ®Google Scholar
• Castro G. D., Castro J. A. Cytosine attack by free radicals arising from bromotrichloromethane in the presence of benzoyl peroxide catalyst. A mass spectrometric study. Terat. Carcing. Mutag. 1993; 13: 235–245
   PubMedGoogle Scholar
• Castro G. D., Díaz Gómez M. I., Castro J. A. Interaction of trichloromethyl free radicals with phenylalanine. Arch. Toxicol. 1991; 65: 340–343
   PubMed Web of Science ®Google Scholar
• Castro G. D., Simpson J. T., Castro J. A. Interaction of trichloromethyl free radicals with thymine in a model system. A mass spectrometric study. Chem.-Biol. Interact. 1994; 90: 13–22
   PubMed Web of Science ®Google Scholar
• Castro J. A. Mechanistical studies and prevention of free radical cell injury. Proc. 9th. (IUPHAR) Intl. Congress Pharmacol. Macmillan Press, London 1984; 2: 243–250
   Google Scholar
• Castro J. A. Prevention of chemically induced liver injury. Toxic Interactions Between Chemicals. Mechanisms and Effects, R. S. Goldstein, W. Hewitt, J. B. Hook. Academic Press, New York 1990; 233–257
   Google Scholar
• Castro J. A., Sasame H. A., Sussman H., Gillette J. R. Diverse effects of SKF525A and antioxidants on carbon tetrachloride-induced changes in liver microsomal P450 content and ethylmorphine metabolism. Life Sci. 1968; 7: 129–136
   PubMed Web of Science ®Google Scholar
• Chofkier M., Lyche K. D., Filip M. Increased production of collagen in vivo by hepatocytes and nonparenchymal cells in rats with carbon tetrachloride-induced hepatic fibrosis. Hepatology 1988; 8: 808–814
   PubMed Web of Science ®Google Scholar
• Darnell J., Lodish H., Baltimore D. Molecular Cell Biology. Scientific American Books, New York 1986; 973–977
   Google Scholar
• Dean R. T., Wolff S. P., McElligott M. A. Histidine and proline are important site of free radical damage to proteins. Free Rod. Res. Commun. 1989; 7: 97–103
   PubMed Web of Science ®Google Scholar
• Dianzani M. U. The role of free radicals in liver damage. Proc. Nut. Soc 1987; 46: 43–52
   PubMed Web of Science ®Google Scholar
• Díaz Gómez M. I., Castro J. A. Covalent binding of carbon tetrachloride metabolites to liver nuclear DNA, proteins and lipids. Toxicol. Appl. Pharmacol. 1980; 56: 199–206
   PubMed Web of Science ®Google Scholar
• Díaz Gómez M. I., Castro J. A. Reaction of trichloromethyl free radicals with deoxyribonucleic acid bases. Res. Commun. Chem. Pathol. Pharmacol. 1981; 32: 147–153
   PubMedGoogle Scholar
• Ehrinpreis M. N., Giambrone M. A., Rojkind M. Liver proline oxidase activity and collagen synthesis in rats with cirrhosis induced by carbon tetrachloride. Biochim. Biophys. Acta 1980; 629: 184–193
   PubMed Web of Science ®Google Scholar
• Frank H., Thiel D., Macleod J. Mass spectrometric detection of crosS-linked fatty acids formed during radical-induced lesion of lipid membranes. Biochem. J. 1989; 260: 873–878
   PubMed Web of Science ®Google Scholar
• Galligani L., Lonati-Galligani M., Fuller G. Collagen metabolism in the liver of normal and carbon tetrachloride-treated rats. Biomedicine 1979; 31: 199–201
   PubMedGoogle Scholar
• IARC. IARC Monographs in the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Some Halogenated Hydrocarbons. Lyon, France 1979; Vol 20: 371–389
   Google Scholar
• Lindblad W. J., Fuller G. C. Hepatic collagenase activity during carbon tetrachloride induced fibrosis. Fundam. Appl. Toxicol. 1983; 3: 34–40
   PubMedGoogle Scholar
• Martinez-Hernandez A. The hepatic extracellular matrix II. Electron inmunohistochemical studies in rats with CCl4-induced cirrhosis. Lab. Invest. 1985; 53: 166–186
   PubMed Web of Science ®Google Scholar
• McGee J. O. D., O'Hare R. P., Patrick R. S. Stimulation of collagen biosynthetic pathway by factors isolated from experimentally injured liver. Nature 1973; 243: 121–123
   Web of Science ®Google Scholar
• Myara I., Miech G., Fabre M., Mangeot M., Lemonnier A. Changes in prolinase and prolidase activity during CC14 administration inducing liver cytolysis and fibrosis in rat. Br. J. Exp. Pathol 1987; 68: 7–13
   PubMed Web of Science ®Google Scholar
• Montfort I., Pérez-Tamayo R. Collagenase in experimental carbon tetrachloride cirrhosis of the liver. Am. J. Pathol. 1978; 92: 411–418
   PubMed Web of Science ®Google Scholar
• Okazaki I., Mamyama K. Collagenase activity in experimental hepatic fibrosis. Nature 1974; 252: 49–50
   PubMed Web of Science ®Google Scholar
• Perez-Tamayo R. Cirrhosis of the liver. A reversible disease?. Pathol. Ann. 1979; 14: 183–213
   Google Scholar
• Recknagel R. O. Carbon tetrachloride hepatotoxicity. Pharmacol. Rev. 1967; 19: 145–208
   PubMed Web of Science ®Google Scholar
• Recknagel R. O., Glende E. A., Dolak J. A., Walter R. L. Mechanisms of carbon tetrachloride toxicity. Pharmacol. Ther. 1986; 43: 139–154
   Google Scholar
• Reuber M. D., Glover E. L. Cirrhosis and carcinoma of the liver in male rats given subcutaneous carbon tetrachloride. J. Natl. Cancer. Inst. 1970; 44: 419–427
   PubMed Web of Science ®Google Scholar
• Rojkind M. The extracellular matrix. The Liver: Biology and Pathobiology, I. Arias, H. Popper, D. Schachter, D. A. Shafritz. Raven Press, New York 1982a; 537–548
   Google Scholar
• Rojkind M. Fibrogenesis. The Liver: Biology and Pathobiology, I. Arias, H. Popper, D. Schachter, D. A. Shafritz. Raven Press, New York 1982b; 801–809
   Google Scholar
• Sasame H. A., Castro J. A., Gillette J. R. Studies on the destruction of liver microsomal cytochrome P450 by carbon tetrachloride administration. Biochem. Pharmacol. 1968; 17: 1759–1768
   PubMed Web of Science ®Google Scholar
• Siegel R. C, Chen K. H., Greenspan J. S., Aguiar J. M. Biochemical and inmunochemical study of lysyl oxidase in experimental hepatic fibrosis in the rat. Proc. Natl. Acad. Sci. (USA) 1978; 75: 2945–2949
   PubMed Web of Science ®Google Scholar
• Slater T. F. Activation of carbon tetrachloride: Chemical principles and biological significance. Free Radicals, Lipid Peroxidation and Cancer, D. C. H. McBrien, T. F. Slater. Academic Press, New York 1982; 243–274
   Google Scholar
• Smuckler E. A., Arcasoy M. Structural and functional changes of the endoplasmic reticulum of hepatic parenchymal cells. Int. Rev. Exp. Pathol. 1969; 7: 305–418
   PubMedGoogle Scholar
• USEPA. Health assessment document for carbon tetrachloride. EPA, Washington, DC. 1983, 600/8–82–001
   Google Scholar
• Villarruel M. C, Castro J. A. Reactions of trichloromethyl free radicals with amino acids. Res. Commun. Chem. Pathol. Pharmacol. 1980; 28: 79–85
   PubMedGoogle Scholar
• Von Oettingen W. F. The Halogenated Aliphatic, Olefinic, Cyclic, Aromatic and Aliphatic-Aromatic Hydrocarbons Including the Halogenated Insecticides. Their Toxicity and Potential Dangers. US Department of HEWGPO, Washington, DC 1955; 75–112
   Google Scholar