Biotransformation of Diethenylbenzenes. I. Identification of the Main Urinary Metabolites of 1,4-Diethenylbenzene in the Rat

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
• Bardoêj Z. Styrene metabolism. Ceskoslovenská Hygiena 1964; 9: 223–239, (in Czech)
   PubMedGoogle Scholar
• Bergemalm‐Rynell K., Steen G. Urinary metabolites of vinyltoluene in the rat. Toxicology and Applied Pharmacology 1982; 62: 19–31
   PubMedGoogle Scholar
• Chasseaud L. F. Conjugation with glutathione and mercapturic acid excretion. Glutathione: Metabolism and Functions, I. M. Arias, W. B. Jakoby. Raven Press, New York 1976; 77–114
   Google Scholar
• Delbressine L. P. C., Ketelaars H. C. J., Seutter‐Berlage F., Smeets F. L. M. Phenaceturic acid, a new urinary metabolite of styrene in the rat. Xenobiotica 1980; 10: 337–342
   PubMed Web of Science ®Google Scholar
• van Doorn R., Leijdekkers Ch. ‐M., Bos R. P., Brouns R. M. E., Henderson P. T. Enhanced excretion of thioethers in urine of operators of chemical waste incinerators. British Journal of Industrial Medicine 1981; 38: 187–190
   PubMedGoogle Scholar
• Duverger‐van Bogaert M., Noel G., Rollman B., Cumps J., Roberfroid M., Mercier M. Determination of oxide synthetase and hydratase activities by a new highly sensitive gas chromatographic method using styrene and styrene oxide as substrates. Biochimical et Biophysica Acta 1978; 526: 77–84
   PubMed Web of Science ®Google Scholar
• El‐Masri A. M., Smith J. N., Williams R. T. Studies on detoxication. The metabolism of alkylbenzenes: phenylacetylene and phenylethylene (styrene). Biochemical Journal 1958; 68: 199–204, Environmental Health Criteria, 26: Styrene, pp. 12–14 (Geneva: World Health Organisation), (1983)
   PubMedGoogle Scholar
• Hamer G. K., Peat J. R., Reynolds W. F. Investigations of substituent effects by nuclear magnetic resonance spectroscopy and all‐valence electron molecular orbital calculations. I. 4‐Substituted styrenes. Canadian Journal of Chemistry 1973; 51: 897–910
   Web of Science ®Google Scholar
• Heinonen T. H. H. Metabolism of vinyltoluene in the rat: Effect of induction and inhibition of the cytochrome P‐450. Biochemical Pharmacology 1984; 33: 321–328
   Google Scholar
• James L. D., White D. A. The metabolism of phenethyi bromide, styrene and styrene oxide in the rabbit and rat. Biochemical Journal 1967; 104: 914–921
   PubMed Web of Science ®Google Scholar
• Leibman K. C. Metabolism and toxicity of styrene. Environmental Health Perspectives 1975; 11: 115–119
   PubMedGoogle Scholar
• Leibman K. C., Ortiz E. Oxidation of styrene in liver microsomes. Biochemical Pharmacology 1969; 18: 552–554
   PubMed Web of Science ®Google Scholar
• Linhart I., Šmejkal J. Changes in the excretion of endogeneous glycine conjugates as a possible artifact in toxicological experiments. Archives of Toxicology 1987; 61: 83–85
   PubMedGoogle Scholar
• Linnainmoa K., Meretoja T., Sorsa M., Vainio H. Cytogenetic effects of styrene and styrene oxide on human lymphocytes and Allium cepa. Scandinavian Journal of Work and Environmental Health 1978; 4(Suppl. 2)156–162
   PubMedGoogle Scholar
• Maltoni O., Failla G., Kassapidis G. First experimental demonstration of the carcinogenic effects of styrene oxide. Long‐term bioassays on Sprague‐Dawley rats by oral administration 1979; 70: 358–362
   Google Scholar
• Ohtsuji H., Ikeda M. The metabolism of styrene in rat and the stimulatory effect of phenobarbital. Toxicology and Applied Pharmacology 1971; 18: 321–328
   PubMed Web of Science ®Google Scholar
• Seutter‐Berlage F., van Dorp H. L., Kosse H. G. J., Henderson P. T. Urinary mercapturic acid excretion as a biological parameter of exposure to alkylating agents. International Archives of Occupational and Environmental Health 1977; 39: 45–51
   PubMed Web of Science ®Google Scholar
• Seutter‐Berlage F., Delbressine L. P. C., Smeets F. L. M., Ketelaars H. C. J. Identification of three sulphur‐containing urinary metabolites of styrene in the rat. Xenobiotica 1978; 8: 413–418
   PubMed Web of Science ®Google Scholar
• Sharief Y., Brown A. M., Backer L. C., Campbell J. A., Westbrook‐Collins B. Sister chromatid exchange and chromosome aberation analyses in mice after in vivo exposure to acrylonitrile, styrene, or butadiene monoxide. Environmental Mutagenetics 1986; 8: 439–448
   PubMedGoogle Scholar
• Šmejkal J., Kopecký J., Linhart I. Preparation of pure 1,4‐divinylbenzene. Zeitschrift für Chemie 1986; 26: 397–398, (in German)
   Google Scholar
• Tamura N., Takahashi K., Shirai N., Kawazoe Y. Studies on chemical carcinogens. XXI. Quantitative structure‐mutagenicity relationship among substituted styrene oxides. Chemical and Pharmaceutical Bulletins 1982; 30: 1393–1400
   PubMedGoogle Scholar
• Touchstone J. C., Dobbins M. R. Practise of Thin Layer Chromatography. John Wiley, New York, Chichester, Brisbane, Toronto 1978; 174, 179, 184
   Google Scholar
• Vainio H. Vinyl chloride and vinyl benzene (styrene) metabolism, mutagenicity and carcinogenicty. Chemico‐Biological Interactions 1978; 22: 117–124
   PubMed Web of Science ®Google Scholar
• Watabe T., Ozawa N., Yoshikawa K. The metabolism of styrene, racemic (R)‐(+), and (S)‐( — )phenyloxiranes in the rat. Journal of Pharmacobio.‐Dynamics 1982; 5: 129–133
   PubMedGoogle Scholar
• Yagen B., Hernandez O., Bend J. R., Cox R. H. Synthesis and relative stereochemistry of the benzylic thioether diastereomers formed from glutathione and styrene oxide. Bioorganic Chemistry 1981; 10: 299–310
   Web of Science ®Google Scholar