Relationship between hydrocarbon structure and induction of P450: effects on protein levels and enzyme activities

References

• Bakke O. M., Scheline R. R. Hydroxylation of aromatic hydrocarbons in the rat. Toxicology and Applied Pharmacology 1970; 16: 691–700
   PubMed Web of Science ®Google Scholar
• Blake M. S., Johnston K. H., Russell-Jones G. J., Gotschlich E. C. A rapid, sensitive method for detection of alkaline phosphatase-conjugated anti-antibody on Western blots. Analytical Biochemistry 1984; 136: 175–179
   PubMed Web of Science ®Google Scholar
• Carlone M. F., Fouts J. R. In vitro metabolism of p-xylene by rabbit lung and liver. Xenobiotica 1974; 4: 705–715
   Web of Science ®Google Scholar
• Chapman D. E., Moore T. J., Michener S. R., Powis G. Metabolism and covalent binding of (C14)toluene by human and rat liver microsomal fractions and liver slices. Drug Metabolism and Disposition 1990; 18: 929–936
   PubMed Web of Science ®Google Scholar
• Cochin J., Axelrod J. Biochemical and pharmacological changes in the rat following chronic administration of morphine, nalorphine and normorphine. Journal of Pharmacology and Experimental Therapeutics 1959; 125: 105–110
   PubMed Web of Science ®Google Scholar
• Cohr K. H., Stokholm J. Toluene: a toxicologic review. Scandinavian Journal of Work and Environmental Health 1979; 5: 71–90
   PubMed Web of Science ®Google Scholar
• El Masry A. M., Smith J. N., Williams R. T. The metabolism of alkylbenzenes: n-propylbenzene and n-butylbenzene with further observations on ethylbenzene. Biochemical Journal 1956; 64: 50–56
   PubMed Web of Science ®Google Scholar
• Elovaara E., Engstrom K., Vainio H. Metabolism and disposition of simultaneously inhaled m-xylene and ethylbenzene in the rat. Toxicology and Applied Pharmacology 1984; 75: 466–478
   PubMed Web of Science ®Google Scholar
• Fishbein L. An overview of environmental and toxicological aspects of aromatic hydrocarbons I. Benzene. Science and the Total Environment 1984; 40: 189–218
   PubMed Web of Science ®Google Scholar
• Fishbein L. An overview of environmental and toxicological aspects of aromatic hydrocarbons II. Toluene. Science and the Total Environment 1985a; 42: 267–288
   PubMed Web of Science ®Google Scholar
• Fishbein L. An overview of environmental and toxicological aspects of aromatic hydrocarbons III. Xylene. Science and the Total Environment 1985b; 43: 165–183
   PubMed Web of Science ®Google Scholar
• Fishbein L. An overview of environmental and toxicological aspects of aromatic hydrocarbons IV. Ethylbenzene. Science and the Total Environment 1985c; 44: 269–287
   PubMed Web of Science ®Google Scholar
• Gonzalez F. J. The molecular biology of cytochrome P450s. Pharmacological Review 1989; 40: 243–288
   Web of Science ®Google Scholar
• Gonzalez F. J. Molecular genetics of the P-450 superfamily. Pharmacological Therapeutics 1990; 45: 1–38
   PubMed Web of Science ®Google Scholar
• Hanzilik R. P., Hogberg K., Judson C. M. Microsomal hydroxylation of specifically deuterated monosubstituted benzenes. Evidence for direct aromatic hydroxylation. Biochemistry 1984; 23: 3048–3055
   Google Scholar
• Imaoka S., Funae Y. Induction of cytochrome P450 isozymes in rat liver by methyl n-alkyl ketones and n-alkylbenzenes. Effects of hydrophobicity of inducers on inducibility of cytochrome P450. Biochemical Pharmacology 1991; 42S: 143–150
   Google Scholar
• Imai Y., Ito A., Sato R. Evidence for two forms of P450 hemoprotein in microsomal membranes. Journal of Biochemistry (Tokyo) 1966; 60: 417–428
   PubMed Web of Science ®Google Scholar
• Jerina D. M., Daly J. W. Arene oxides: a new aspect of drug metabolism. Science 1974; 185: 573–582
   PubMed Web of Science ®Google Scholar
• Johansson I., Ingelman-Sundberg M. Benzene metabolism by ethanol-, acetone-, and benzene-inducible cytochrome P-450 (IIE1) in rat and rabbit liver microsomes. Cancer Research 1988; 48: 5387–5390
   PubMed Web of Science ®Google Scholar
• Koop D. R., Crump B. L., Nordblom G. D., Coon M. J. Immunochemical evidence for induction of the alcohol-oxidizing cytochrome P-450 of rabbit liver microsomes by diverse agents: ethanol, imidazole, trichloroethylene, acetone, pyrazole, and isoniazid. Proceedings of the National Academy of Sciences, USA 1985; 82: 4065–4069
   PubMed Web of Science ®Google Scholar
• Koop D. R., Tierney D. J. Multiple mechanisms in the regulation of ethanol-inducible cytochrome P450IIE1. BioEssays 1990; 12: 429–435
   PubMed Web of Science ®Google Scholar
• Koop D. R., Laethem C. L., Schinier G. G. Identification of ethanol-inducible P450 isozyme 3 a (P450IIE1) as a benzene and phenol hydroxylase. Toxicology and Applied Pharmacology 1989; 98: 278–288
   PubMed Web of Science ®Google Scholar
• Layne E. Spectrophotometric and turbidimetric methods for measuring proteins. Methods in Enzymology 1957; 3: 447–454
   Web of Science ®Google Scholar
• Matsumoto T., Koga M., Sata T., Kadoya T., Shigematsu A. The changes of gasoline compounds in blood in a case of gasoline intoxications. Journal of Toxicology and Clinical Toxicology 1992; 30: 653–662
   PubMed Web of Science ®Google Scholar
• Nakajima T., Elovaara E., Park S. S., Gelboin H. V., Hietanen E., Vainio H. Immunochemical characterization of cytochrome P-450 isozymes responsible for benzene oxidation in the rat liver. Carcinogenesis 1989; 10: 1713–1717
   PubMed Web of Science ®Google Scholar
• Nakajima T., Wang R. S., Elovaara E., Park S. S., Gelboin H. V., Hieyanen E., Vainio H. Monoclonal antibody-directed characterization of cytochrome P450 isozymes responsible for toluene metabolism in rat liver. Biochemical Pharmacology 1991; 41: 395–404
   PubMed Web of Science ®Google Scholar
• Nash T. The colorimetric estimation of formaldehyde by means of the Hantzsch reaction. Biochemical Journal 1953; 55: 416–421
   PubMed Web of Science ®Google Scholar
• Netter K. J., Seidel G. An adaptively stimulated O-demethylating system in rat liver microsomes and its kinetic properties. Journal of Pharmacology and Experimental Therapeutics 1964; 146: 61–65
   PubMed Web of Science ®Google Scholar
• Ogan K., Katz E. Liquid chromatographic separation of alkylphenols with fluorescence and ultraviolet detection. Annals of Chemistry 1981; 53: 160–163
   Google Scholar
• Omura T., Sato R. The carbon monoxide-binding pigment of liver microsomes: II. Solubilization, purification, and properties. Journal of Biological Chemistry 1964; 239: 2379–2385
   PubMed Web of Science ®Google Scholar
• Okey A. B. Enzyme induction in the cytochrome P-450 system. Pharmacological Therapeutics 1990; 45: 241–298
   PubMed Web of Science ®Google Scholar
• Pathiratne A., Puyear R. L., Brammer J. D. A comparative study of the effects of benzene, toluene, and xylenes on their in vitro metabolism and drug-metabolizing enzymes in rat liver. Toxicology and Applied Pharmacology 1986; 82: 272–280
   PubMed Web of Science ®Google Scholar
• Prough R. A., Burke M. D., Mayer R. T. Direct fluorometric methods for measuring mixed-function oxidase activity. Methods in Enzymology 1978; 52: 372–377
   PubMedGoogle Scholar
• Pyykkö K. Effects of methylbenzenes on microsomal enzymes in rat liver, kidney, and lung. Biochimica et Biophysica Acta 1980; 633: 1–9
   PubMed Web of Science ®Google Scholar
• Remmer H., Schenkman J. B., Estabrook R. W., Sasame H., Gillette J., Cooper D. Y., Narasimhulu S., Rosenthal O. Drug interaction with hepatic microsomal cytochrome. Molecular Pharmacology 1966; 2: 187–190
   PubMed Web of Science ®Google Scholar
• Ryan D. E., Levin W. Purification and characterization of hepatic microsomal cytochrome P-450. Pharmacology and Therapeutics 1989; 45: 153–239
   Google Scholar
• Saito F. U., Kocsis J. J., Snyder R. Effect of benzene on hepatic drug metabolism and ultrastructure. Toxicology and Applied Pharmacology 1973; 26: 209–217
   PubMed Web of Science ®Google Scholar
• Schellenberg K. A., Hellerman L. Oxidation of reduced diphosphopyridine nucleotide. Journal of Biological Chemistry 1957; 231: 547–556
   Google Scholar
• Sedivec V., Flek J. The absorption, metabolism and excretion of xylenes in man. International Archives of Occupational and Environmental Health 1976; 37: 205–217
   PubMed Web of Science ®Google Scholar
• Sequeira D. J., Eyer C. S., Cawley G. F., Nick T. G., Backes W. L. Ethylbenzene-mediated induction of cytochrome P450 isozymes in male and female rats. Biochemical Pharmacology 1992; 44: 1171–1182
   PubMed Web of Science ®Google Scholar
• ToftÅRd R., Gustafsson J. A. Biotransformation of organic solvents. Scandinavian Journal of Work and Environental Health 1980; 6: 1–18
   Google Scholar
• ToftgÅRd R., Eng T., Haaparanta L., Halpert J. Rat lung and liver cytochrome P-450 isozymes involved in the hydroxylation of n-hexane. Biochemical Pharmacology 1986b; 35: 3733–3738
   PubMed Web of Science ®Google Scholar
• ToftgÅRd R., Haaparanta T., Halpert J. Rat lung and liver cytochrome P-450 isozymes involved in the hydroxylation of m-xylene. Toxicology 1986a; 39: 225–231
   PubMed Web of Science ®Google Scholar
• ToftgÅRd R., Halpert J., Gustafsson J.-Å. Xylene induces a cytochrome P450 isozyme in fat liver similar to the major isozyme induced by phenobarbital. Molecular Pharmacology 1983; 23: 265–271
   PubMed Web of Science ®Google Scholar
• ToftgÅRd R., Nilson O. G. Effects of xylene and xylene isomers on cytochrome F-450 and in vitro enzymatic activities in rat liver, kidney, and lung. Toxicology 1982; 23: 197–212
   PubMed Web of Science ®Google Scholar
• Towbin H., Stailin T., Gordin J. Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets: procedure and some applications. Proceedings of the National Academy of Sciences, USA 1979; 76: 4350–4354
   PubMed Web of Science ®Google Scholar
• Ullrich V., Weber P. The O-dealkylation of 7-ethoxycoumarin by liver microsomes. A direct fluorometric test. Hoppe-Seyler's Zeitschrift für Physiologische Chemie 1972; 353: 1171–1177
   PubMedGoogle Scholar
• Woiwode W., Drysch R., Wodarz K., Weichardt H. Metabolism of toluene in man: gas-chromatographic determination of o-, m-, and p-cresol in urine. Archives of Toxicology 1979; 43: 93–98
   PubMed Web of Science ®Google Scholar
• Yonetani T. Studies on cytochrome c peroxidase. II. Stoichiometry between enzyme, H2O2, and ferrocytochrome c and enzymic determination of extinction coefficients of cytochrome c. Journal of Biological Chemistry 1965; 240: 4509–4514
   PubMedGoogle Scholar