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Xenobiotica
the fate of foreign compounds in biological systems
Volume 29, 1999 - Issue 1
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Research Article

Quantitative studies on the urinary metabolic fate of 2-chloro-4-trifluoromethylaniline in the rat using 19F-NMR spectroscopy and directly coupled HPLCNMR-MS

Pages 77-91 | Published online: 22 Sep 2008

References

  • BOOTH, J. and BOYLAND, E. 1964, The biochemistry of aromatic amines: enzymic N-hydroxylation of arylamines and conversion of arylhydroxylamines into o-aminophenols. Biochemical journal, 91, 362–369.
  • BURLINGAME, A. L., BAILLIE, T. A. and RUSSELL, D. H., 1992, Mass spectrometry. Analytical Chemistry, 64, 467R–502R.
  • BURTON, K. I., EVERETT, J. R., NEWMAN, M. J., PULLEN, F. S., RICHARDS, D. S. and SWANSON, A. G., 1997, On-line liquid chromatography coupled with high field NMR and mass spectrometry (LC-NMR-MS): a new technique for drug metabolite structure elucidation. Journal of Pharmaceutical and Biomedial Analysis, 15, 1903–1912.
  • CUPID, B. C., BEDDELL, C. R., WILSON, I. D., LINDON J. C. and NICHOLSON, J. K., 1996, Quantitative structure-metabolism relationships for substituted benzoates in the rabbit: prediction of urinary excretion of glycine and glucuronide conjugates. Xenobiotica, 26, 157–176.
  • EHLHARDT W. J. and HOWBERT J. J., 1991, Metabolism and disposition of p-chloroaniline in rat, mouse, and monkey. Drug Metabolism and Disposition, 19, 366–369.
  • GHAURI, F. Y., BLACKLEDGE C. A., GLEN, R. C., SWEATMAN, B. C., LINDON J. C., BEDDELL C. R., WILSON, I. D. and NICHOLSON, J. K., 1992a, An approach to a metabolic expert system: structure—metabolism relationships for benzoic acids in the rat. In E. Reid and D. Wilson (eds), Methodological Surveys in Biochemistry and Analysis (Cambridge: Royal Society of Chemistry), pp. 21–28.
  • GHAURI, F. Y., BLACKLEDGE C. A., GLEN, R. C., SWEATMAN, B. C., LINDON J. C., BEDDELL C. R., WILSON, I. D. and NICHOLSON, J. K., 1992b, Quantitative structure-metabolism relationships of substituted benzoic acids in the rat. Computational chemistry, NMR spectroscopy and computer pattern recognition studies. Biochemical Pharmacology, 44, 1935–1946.
  • HOLMES, E., SWEATMAN, B. C., BOLLARD, M., BLACKLEDGE, C. A., BEDDELL, C. R., WILSON, I. D., LINDON, J. C. and NICHOLSON, J. K., 1995, Prediction of urinary sulphate and glucuronide excretion of substituted phenols in the rat using quantitative structure—metabolism relationships. Xenobiotica, 25, 1269–1281.
  • HOLT, R. M., NEWMAN, M. J., PULLEN, F. S., RICHARDS, D. S. and SWANSON, A. G., 1997, High-performance liquid chromatography/NMR spectrometry/mass spectrometry: further advances in hyphenated technology. Journal of Mass Spectrometry, 32, 64–70.
  • KADLUBAR, F. F., MILLER, J. A. and MILLER, E. C., 1977, Hepatic microsomal N-glucuronidation and nucleic acid binding of N-hydroxy arylamines in relation to urinary bladder carcinogenesis. Cancer Research, 37, 805–814.
  • KIESE, M. and LENK, W., 1971, Metabolites of 4-chloroaniline and chloroacetanilides produced by rabbits and pigs. Biochemical Pharmacology, 20, 379–391.
  • LINDON, J. C., NICHOLSON, J. K. and WILSON, I. D., 1996, Direct coupling of chromatographic separations to NMR spectroscopy. Progress in Nuclear Magnetic Resonance Spectroscopy, 29, 1–49.
  • MUTLIB, A. E., STRUPCZEWSKI, J. T. and CHESSON S. M., 1995, Application of hyphenated LC/NMR and LC/MS techniques in rapid identification of in vitro and in vivo metabolites of iloperidone. Drug Metabolism and Disposition, 23, 951–964.
  • PULLEN, F. S., SWANSON, A. G., NEWMAN, M. J. and RICHARDS, D. S., 1995, 'On-line' liquid chromatography/nuclear magnetic resonance mass spectrometry. A powerful spectroscopic tool for the analysis of mixtures of pharmaceutical interest. Rapid Communications in Mass Spectrometry, 9, 1003–1006.
  • RADOMSKI, J. L., 1979, The primary aromatic amines: their biological properties and structure-activity relationships. Annual Reviews in Pharmacological Toxicology 19, 129–157.
  • RADOMSKI, J. L., HEARN, W. L., RADOMSKI, T., MORENO, H. and SCOTT, W. E., 1977, Isolation of the glucuronic acid conjugate of N-hydroxy-4-aminobiphenyl from dog urine and its mutagenic activity. Cancer Research, 37, 1757–1762.
  • SCARFE, G. B., WILSON, I. D., SPRAUL, M., HOFMANN, M., BRAUMANN U., LION, J. C. and NICHOLSON, J. K., 1997, Application of directly coupled high performance liquid chromato-graphy—nuclear magnetic resonance—mass spectrometry to the detection and characterisation of the metabolites of 2-bromo-4-trifluoromethylaniline in rat urine. Analytical Communications, 34, 37–39.
  • SCARFE, G. B., WRIGHT, B., CLAYTON, E., TAYLOR, S., WILSON, I. D., LINDON, J. C. and NICHOLSON, J. K., 1998, '9 F-NMR and directly coupled HPLC-NMR-MS investigations into the metabolism of 2-bromo-4-trifluoromethylaniline in the rat: urinary excretion balance study without the use of radiolabelling. Xenobiotka, 28,373–388.
  • SHocKcoR, J. P., UNGER, S. E., WILSON, I. D., FOXALL, P. J. D., NICHOLSON, J. K. and LINDON, J. C., 1996, Combined HPLC, NMR spectroscopy, and ion-trap mass spectrometry with application to the detection and characterization of xenobiotic and endogenous metabolites in human urine. Analytical Chemistry, 68,4431–4435.
  • STERNSON, L. A. and GAMMANS, R. E., 1974, A mechanistic study of aromatic hydroxylamine rearrangement in the rat. Bioorganic Chemistry, 4,58–63.
  • WADE, K. E., TROKE, J., MACDONALD, C. M., WILSON, I. D. and NICHOLSON, J. K., 1988, NMR studies of the metabolism of trifluoromethylaniline. In E. Reid, J. D. Robinson and I. D. Wilson (eds), Bioanalysis of Drugs and Metabolites (New York: Plenum) pp. 383–388.
  • WILSON, I. D., MACDONALD, C. M., FROMSON, J. M., TROKE, J. A. and HILLBECK, D., 1985, Species differences in the metabolism of ' C-p-trifluoromethylaniline : production of an oxanilic acid as the major metabolite by the rat. Biochemical Pharmacology, 34,2025–2028.

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