Occurrence of the NIH shift upon the cytochrome P450-catalyzed in vivo and in vitro aromatic ring hydroxylation of fluorobenzenes

Chemical Research in Toxicology

Volumn 11, Issue 5, 1998, Pages 503-512

  Koerts, Janneke ^a   Soffers, Ans E M F ^a   Vervoort, Jacques ^a   De Jager, Adrie ^a,b   Rietjens, Ivonne M C M ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b Department of Molecular Physics ^*

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; EPOXIDE; FLUOROBENZENE;

ANIMAL EXPERIMENT; ARTICLE; CATALYSIS; CONJUGATION; DATA ANALYSIS; FLUORINATION; HALOGENATION; HYDROXYLATION; MALE; MICROSOME; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; RAT; URINALYSIS;

ANIMALS; CHEMISTRY, PHYSICAL; CYTOCHROME P-450 ENZYME SYSTEM; CYTOSOL; FLUOROBENZENES; GLUTATHIONE; HYDROXYLATION; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MICROSOMES, LIVER; MIXED FUNCTION OXYGENASES; RATS; RATS, WISTAR; TRICHOSPORON;

EID: 0031777752     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx980053i     Document Type: Article

References (42)

1. Guroff, G., Daly, J. W., Jerina, D. M., Renson, J., Witkop, B., and Udenfriend, S. (1967) Hydroxylation-induced migration: The NIH shift. Science 157, 1524-1530.
2. Daly, J. W., Jerina, D. M., and Witkop, B. (1972) Arene oxides and the NIH shift: The metabolism, toxicity and carcinogenicity of aromatic compounds. Experientia 28, 1129-1264.
3. Jerina, D. M., and Daly, J. W. (1974) Arene oxides: A new aspect of drug metabolism. Science 185, 573-582.
4. Korzekwa, K., Trager, W., Gouterman, M., Spangler, D., and Loew, G. H. (1985) Cytochrome P450 mediated aromatic oxidation: A theoretical study. J. Am. Chem. Soc. 107, 4273-4279.
5. Reed, D. J., Vimmerstedt, J., Jerina, D. M., and Daly, J. W. (1973) Formation of phenols from aromatic substrates by plant and animal mono-oxygenases: The effect of adjacent deuteriums on the magnitude of the NIH shift of tritium. Arch. Biochem. Biophys. 154, 642-647.
6. Daly, J., Jerina, D., and Witkop, B. (1968) Migration of deuterium during hydroxylation of aromatic substrates by liver microsomes: I. Influence of ring substituents. Arch. Biochem. Biophys. 128, 517-527.
7. Guroff, G., Kondo, K., and Daly, J. (1966) The production of metachlorotyrosine from para-chlorophenylalanine by phenylalanine hydroxylase. Biochem. Biophys. Res. Commun. 25, 622-628.
8. Counsell, R. E., Chan, P. S., and Weinhold, P. A. (1970) Lack of hydroxylation-induced migration with 4-iodophenylalanine. Biochim. Biophys. Acta 215, 187-188.
9. Kohli, J., Jones, D., and Safe, S. (1976) The metabolism of higher chlorinated benzene isomers. Can. J. Biochem. 54, 203-208.
10. Chu, L. Villeneuve, D. C., Viau, A., Barnes, C. R., Benoit, F. M., and Qin, Y. H. (1984) Metabolism of 1,2,3,4-, 1,2,3,5-, and 1,2,4,5-tetrachlorobenzene in the rat. J. Toxicol. Environ. Health 13, 777-786.
11. Schwartz, H., Chu, I., Villeneuve, D. C., and Benoit, F. M. (1987) Metabolism of 1,2,3,4-, 1,2,3,5-, and 1,2,4,5-tetrachlorobenzene in the squirrel monkey. J. Toxicol. Environ. Health 22, 341-350.
12. Den Besten, C., Ellenbroek, M., Van der Ree, M. A. E., Rietjens, I. M. C. M., and Van Bladeren, P. J. (1992) The involvement of primary and secondary metabolism in the covalent binding of 1,2-and 1,4-dichlorobenzenes. Chem.-Biol. Interact. 84, 259-275.
13. Den Besten, C., Smink, M. C. C., De Vries, E. J., and Van Bladeren, P. J. (1991) Metabolic activation of 1,2,4-trichlorobenzene and pentachlorobenzene by rat liver microsomes: A major role for quinone metabolites. Toxicol. Appl. Pharmacol. 108, 223-233.
14. Bogaards, J. J. P., Van Ommen, B., Wolf, C. R., and Van Bladeren, P. J. (1995) Human cytochrome P450 enzyme selectivities in the oxidation of chlorinated benzenes. Toxicol. Appl. Pharmacol. 132, 44-52.
15. Renson, J., and Bourdon, V. (1968) Hydroxylation et défluorination des dérivés fluores de l'aniline. (Hydroxylation and defluorination of fluorine derivatives of aniline.) Arch. Int. Pharmacodyn. 171, 240-242.
16. Rietjens, I. M. C. M., and Vervoort, J. (1989) Microsomal metabolism of fluoroanilines. Xenobiotica 19, 1297-1305.
17. Daly, J. (1970) Metabolism of acetanilides and anisoles with rat liver microsomes. Biochem. Pharmacol. 19, 2979-2993.
18. Rizk, P. N., and Hanzlik, R. P. (1995) Oxidative and non-oxidative metabolism of 4-iodoanisole by rat liver microsomes. Xenobiotica 25, 143-150.
19. Rietjens, I. M. C. M., and Vervoort, J. (1991) Bioactivation of 4-fluorinated anilines to benzoquinoneimines as primary reaction products. Chem.-Biol. Interact. 77, 263-281.
20. Den Besten, C., Van Bladeren, P. J., Duizer, E., Vervoort, J., and Rietjens, I. M. C. M. (1993) Cytochrome P450-mediated oxidation of pentafluorophenol to tetrafluorobenzoquinone as the primary reaction product. Chem. Res. Toxicol. 6, 674-680.
21. Rietjens, I. M. C. M., and Vervoort, J. (1992) A new hypothesis for the mechanism for cytochrome P-450 dependent aerobic conversion of hexahalogenated benzenes to pentahalogenated phenols. Chem. Res. Toxicol. 5, 10-19.
22. Griffith, O. W. (1982) Mechanism of action, metabolism, and toxicity of buthionine sulfoximine and its higher homologues, potent inhibitors of glutathione synthesis. J. Biol. Chem. 257, 13704-13712.
23. 19F-NMR method for studies on the in vivo and in vitro metabolism of 2-fluoroaniline. Xenobiotica 20, 657-670.
24. Omura, T., and Sato, R. (1964) The carbon monoxide-binding pigment of liver microsomes. 1. Evidence for its hemoprotein nature. J. Biol. Chem. 239, 2370-2378.
25. Sejlitz, T., and Neujahr, H. Y. (1987) Phenol hydroxylase from yeast. A model for phenol binding and an improved purification procedure. Eur. J. Biochem. 170, 343-349.
26. Fleming, I. (1976) Molecular orbitals and frontier Orbitals. In Frontier Orbitals and Organic Chemical Reactions (Fleming, I., Ed.) pp 5-32, John Wiley & Sons, New York.
27. Fukui, K., Yonezawa, T., Nagata, C., and Shingu, H. (1954) Molecular orbital theory of orientation in aromatic, heteroaromatic and other conjugated molecules. J. Chem. Phys. 22, 1433-1442.
28. Rietjens, I. M. C. M., Soffers, A. E. M. F., Veeger, C., and Vervoort, J. (1993) Regioselectivity of cytochrome P-450 catalyzed hydroxylation of fluorobenzenes predicted by calculated frontier orbital substrate characteristics. Biochemistry 32, 4801-4812.
29. Jollow, D. J., Mitchell, J. R., Zampaglione, N., and Gillette, J. R. (1974) Bromobenzene-induced liver necrosis. Protective role of glutathione and evidence for 3,4-bromobenzene oxide as the hepatotoxic metabolite. Pharmacology 11, 151-169.
30. Zheng, J., and Hanzlik, R. P. (1992) Dihydroxylated mercapturic acid metabolites of bromobenzene. Chem. Res. Toxicol. 5, 561-567.
31. Lindsay Smith, J. R., Shaw, B. A. J., and Foulkes, D. M. (1972) Mechanisms of mammalian hydroxylation: Some novel metabo- lites of chlorobenzene. Xenobiotica 2, 215-226.
32. Cnubben, N. H. P., Peelen, S., Borst, J.-W., Vervoort, J., Veeger, C., and Rietjens, I. M. C. M. (1994) Molecular orbital-based quantitative structure-activity relationship for the cytochrome P450-catalyzed 4-hydroxylation of halogenated anilines. Chem. Res. Toxicol 7, 590-598.
33. Rietjens, I. M. C. M., Soffers, A. E. M. F., Hooiveld, G. J. E. J., Veeger, C., and Vervoort, J. (1995) Quantitative structure-activity relationships based on computer calculated parameters for the overall rate of glutathione S-transferase catalyzed conjugation of a series of fluoronitrobenzenes. Chem. Res. ToxicoL 8, 481-488.
34. Soffers, A. E. M. F., Ploemen, J. H. T. M., Moonen, M. J. H., Wobbes, Th., Van Ommen, B., Vervoort, J., Van Bladeren, P. J., and Rietjens, I. M. C. M. (1996) Regioselectivity and quantitative structure-activity relationships for the conjugation of a series of fluoronitrobenzenes by purified glutathione S-transferase enzymes from rat and man. Chem. Res. Toxicol 9, 638-646.
35. Zakharieva, O., Grodzicki, M., Trautwein, A. X., Veeger, C., and Rietjens, I. M. C. M. (1996) Molecular orbital study of the hydroxylation of benzene and monofluorobenzene catalysed by iron-oxo porphyrin π cation radical complexes. J. Biol. Inorg. Chem. 1, 192-204.
36. 14C]benzene in rats after repeated inhalation, oral and subcutaneous doses. Xenobiotica 10, 81-95.
37. Hanzlik, R. P., Hogberg, K., and Judson, C. M. (1984) Microsomal hydroxylation of specifically deuterated monosubstituted benzenes. Evidence for direct aromatic hydroxylation. Biochemistry 23, 3048-3055.
38. Korzekwa, K. R., Swinney, D. C., and Trager, W. F. (1989) Isotopically labeled chlorobenzenes as probes for the mechanism of cytochrome P450 catalyzed aromatic hydroxylation. Biochemistry 28, 9019-9027.
39. Rizk, P. N., and Hanzlik, R. P. (1995) Oxidative and non-oxidative metabolism of 4-iodoanisole by rat liver microsomes. Xenobiotica 25, 143-150.
40. Rietjens, I. M. C. M., Den Besten, C., Hanzlik, R. P., and Van Bladeren, P. J. (1996) Cytochrome P450-catalyzed oxidation of halobenzene derivatives. Chem. Res. Toxicol. 10, 629-635.
41. Monks, T. J., Lau, S. S., and Gillette, J. R. (1984) Diffusion of reactive metabolites out of hepatocytes: Studies with bromobenzene. J. Pharmacol. Exp. Ther. 228, 393-399.
42. Lau, S. S., and Zannoni, V. G. (1979) Hepatic microsomal epoxidation of bromobenzene to phenols and its toxicologie implication. Toxicol. Appl. Pharmacol. 50, 309-318.