1H and 19F-nmr spectroscopic studies on the metabolism and urinary excretion of mono- and disubstituted phenols in the rat

Xenobiotica

Volumn 26, Issue 3, 1996, Pages 255-273

  Bollard, M E ^a   Holmes, E ^a   Blackledge, C A ^a   Lindon, J C ^b   Wilson, I D ^c   Nicholson, J K ^a  

^a UNIVERSITY OF LONDON   (United Kingdom)

^b WELLCOME RESEARCH LABORATORIES   (United Kingdom)

^c ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOL DERIVATIVE; FLUORINE; PROTON;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; GLUCURONIDATION; MALE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT; STRUCTURE ACTIVITY RELATION; SULFATION; URINARY EXCRETION; XENOBIOTIC METABOLISM; ANIMAL; METABOLISM; METHODOLOGY; SPRAGUE DAWLEY RAT; URINE;

ANIMALS; FLUORINE; MAGNETIC RESONANCE SPECTROSCOPY; MALE; PHENOLS; PROTONS; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0029666249     PISSN: 00498254     EISSN: None     Source Type: Journal    
DOI: 10.3109/00498259609046706     Document Type: Article

References (26)

1. ABOU-EL-MAKAREM, M. M., MILLBURN, P., SMITH, R. L., and WILLIAMS, R. T., 1967, Biliary excretion of foreign compounds. Biochemical Journal 105, 1289-1293.
2. BETEILLE, J. P., LOPEZ, A., BON, M., MALET-MARTINO, C., and MARTINO, R., 1985, Simultaneous assay of organic fluorine compounds in biologicasl fluids by fluorine-19 nuclear magnetic resonance spectrometry over a large spectral width: application to fluoropyrimidines. Analytica Chimica Acta 17, 225-231.
3. 19F NMR spectroscopy study of the metabolites of flucloxacillin in rat urine. Journal of Pharmaceutics and Pharmacology, 37, 869-873.
4. FREIGENBAUM, J., and NEUBERG, C. A., 1941, Simplified method for the preparation of aromatic sulfuric acid esters. Journal of the American Chemical Society 63, 3529-3530.
5. 1H-NMR spectroscopy. Journal of Pharmaceutical and Biomedical Analysis, 8, 939-944.
6. GHAURI, F. Y., BLACKLEDGE, C. A., GLEN, R. C., LINDON, J. C., BEDDELL, C. R., WILSON, I. D., and NICHOLSON, J. K., 1992, Quantitative structure-metabolism relationships for substituted benzoic acids in the rat: computational chemistry, NMR spectroscopy and pattern recognition studies. Biochemical Pharmacology, 44, 1935-1946.
7. GIBSON, G. G., and SKETT, P., 1986, Pharmacological and toxicological aspects of drug metabolism. In Introduction to Drug Metabolism (eds G. G. Gibson and P. Skett (Glasgow: Chapman & Hall), pp. 175-198.
8. HIROM, P. C., MILLBURN, P., SMITH, R. L., and WILLIAMS, R. T., 1972, Species variation in the threshold molecular-weight factor for the biliary excretion of organic anions. Biochemical Journal, 129, 1071-1077.
9. HOLMES, E., BOLLARD, M. E., BLACKLEDGE, C. A., BEDDELL, C. R., WILSON, I. D., LINDON, J. C., and NICHOLSON, J. K., 1995, Quantitative-structure-metabolism relationships for substituted phenols in the rat: prediction of urinary sulphate and glucuronide conjugate excretion. Xenobiotica, 25, 1269-1282.
10. MALET-MARTINO, M. C., and MARTINO, R., 1989, Application of nuclear magnetic resonance spectroscopy to drug metabolism studies. Xenobiotica, 19, 583-607.
11. MULDER, G. J., and BLEEKE, B., 1975, UDP glucuronyltransferase and phenolsulphotransferase from rat liver in vivo and in vitro. Biochemical Pharmacology, 24, 103-107.
12. MULDER, G. J., and SCHOLTENS, E., 1977, Phenol sulphotransferase and uridine diphosphate glucuronyltransferase from rat liver in vivo and in vitro. Biochemical Journal, 165, 553-559.
13. MULDER, G. J., 1984, Sulphation-metabolic aspects. Progress in Drug Metabolism, 8, pp. 35-100.
14. MULDER, G. J., 1990, Competition between conjugations for the same substrate. In Conjugation Reactions in Drug Metabolism, ed. G. J. Mulder (London: Taylor & Francis Ltd), pp. 41-50.
15. NICHOLSON, J. K., and WILSON, I. D., 1989, High resolution proton magnetic resonance spectroscopy of biological fluids. Progress in NMR Spectroscopy, 21, 444-501.
16. PARK, K. B., and KITTERINGHAM, N. R., 1994, Effects of fluorine substitution on drug metabolism: Pharmacological and toxicological implications. Drug Metabolism Reviews, 26, 605-643.
17. 19F-NMR study on the pH-dependent regioselectivity and rate of ortho-hydroxylation of 3-fluorophenol by phenol hydroxylase from Trichlosporon cutaneum: implications for the reaction mechanism. European Journal of Biochemistry, 218, 345-353.
18. RIETJENS, I. M. C. M., and VERVOORT, J., 1989, Microsomal metabolism of fluoroanilines. Xenobiotica, 19, 1297-1305.
19. RIETJENS, I. M. C. M., SOFFER, A. E. M. F., VEEGER, C., and VERVOORT, J., 1993, Regioselectivity of cytochrome P-450 catalysed hydroxylation of fluorobenzenes predicted by calculated frontier orbital substrate characteristics. Biochemistry, 32, 4801-4812.
20. SOFFERS, A. E. M. F., VEEGER, C., and RIETJENS, I. M. C. M., 1994, Influence of the type of halogen substituent on in vivo and in vitro phase II metabolism of 2-fluoro-4-halophenol metabolites formed from 3-halo-fluorobenzenes. Xenobiotica, 24, 759-774.
21. TEMELLINI, A., FRANCHI, M., GIULIANI, L., and PACIFICI, G. M., 1991, Human liver sulphotransferase and UDP-glucuronyltransferase: structure-activity relationship for phenolic substrates. Xenobiotica, 21, 171-177.
22. 19F-NMR method for studies on the in vivo and in vitro metabolism of 2-fluoroaniline. Xenobiotica, 20, 657-670.
23. 1H nuclear magnetic resonance strategies for metabolic studies on fluorinated xenobiotics: application to flurbiprofen ([2-(2-fluoro-4-biphenyl)propionic acid). Journal of Pharmaceutical and Biomedical Analysis, 8, 401-410.
24. WEITERING, J. G., KRIJGSHELD, K. R., and MULDER, G. J., 1979, The availability of inorganic sulphate as a rate limiting factor in the sulphate conjugation of xenobiotics in the rat: sulphation and glucuronidation of phenol. Biochemical Pharmacology, 28, 757-762.
25. WILSON, I. D., and NICHOLSON, J. K., 1987. Solid phase extraction chromatography and NMR spectrometry for the identification and isolation of drug metabolites in urine. Annals of Chemistry, 59, 2830-2832.
26. WILSON, I. D., and NICHOLSON, J. K., 1988, Solid phase extraction chromatography and NMR spectroscopy (SPEC-NMR) for the rapid identification of drug metabolites in urine. Journal of Pharmaceutical and Biomedical Analysis, 6, 151-165.