Influence of the halogen-substituent pattern of fluoronitrobenzenes on their biotransformation and capacity to induce methemoglobinemia

Toxicology and Applied Pharmacology

Volumn 139, Issue 1, 1996, Pages 71-83

  Cnubben, Nicole H P ^a   Soffers, Ans E M F ^a   Peters, Maria A W ^a   Vervoort, Jacques ^a   Rietjens, Ivonne M C M ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

HALOCARBON; NITROBENZENE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BIOTRANSFORMATION; CONTROLLED STUDY; MALE; METHEMOGLOBINEMIA; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALIA; BOVINAE;

EID: 0030200831     PISSN: 0041008X     EISSN: None     Source Type: Journal    
DOI: 10.1006/taap.1996.0144     Document Type: Article

References (32)

1. Akhtar, M., and Wright, J. N. (1991). A unified mechanistic view of oxidative reactions catalyzed by P-450 and related Fe-containing enzymes. Nat. Prod. Rep. 8, 527-551.
2. Beauchamp, R. O., Irons, R. D., Rickert, D. E., Couch, D. B., and Hamm, T. E. (1982). A critical review of the literature on nitrobenzene toxicity. CRC Crit. Rev. Toxicol. 11, 33-84.
3. Cesarone, C. F., Bolognesi, C., and Santi, L. (1983). DNA damage induced in vivo in various tissues by nitrochlorobenzene derivatives. Mut. Res. 116, 239-246.
4. Cnubben, N. H. P., Peelen, S., Borst, J. W., Vervoort, J., 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.
5. Cnubben, N. H. P., Vervoort, J., Veeger, C., and Rietjens, I. M. C. M. (1992). Study on the regioselectivity and mechanisms of the aromatic hydroxylation of monofluoroanilines. Chem. - Biol. Interact. 85, 151-172.
6. Debnath, A. K., Lopez de Compadre, R. L., Debnath, G., Shusterman, A. J., and Hansch, C. (1991). Structure activity relationship of mutagenic aromatic and heteroaromatic nitrocompounds. Correlation with molecular orbital energies and hydrophobicity. J. Med. Chem. 34, 785-797.
7. Debnath, A. K., Lopez de Compadre, R. L., Shusterman, A. J., and Hansch, C. (1992). Quantitative structure activity relationship investigation of the role of hydrophobicity in regulating mutagenicity in the Ames test. 2. Mutagenicity of aromatic and heteroaromatic nitrocompounds in Salmonella typhimurium TA 100. Environ. Mol. Mutagen. 19, 53-70.
8. 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.
9. Harada, N., and Omura, T. (1980). Participation of cytochrome P-450 in the reduction of nitro compounds by rat liver microsomes. J. Biochem. 87, 1539-1554.
10. Harrison, J. H., and Jollow, D. J. (1987). Contribution of aniline metabolites to aniline-induced methemoglobinemia. Mol. Pharmacol. 32, 423-431.
11. Kennedy, R. J., and Stock, A. M. (1960). The oxidation of organic substances by potassium peroxymonosulphate. J. Org. Chem. 25, 1901-1906.
12. Kiese, M. (1974). Methemoglobinemia: A Comprehensive Treatise, Chapt. 7. CRC Press, Cleveland, OH.
13. Levin, A. A., and Dent, J. G. (1982). Comparison of the metabolism of nitrobenzene by hepatic microsomes and cecal microflora from Fischer-344 rats in vitro and the relative importance of each in vivo. Drug Metab. Dispos. 10, 450-454.
14. Lopez de Compadre, R. L., Debnath, A. K., Shusterman, A. J., and Hansch, C. (1990). LUMO energies and hydrophobicity as determinants of mutagenicity by nitroaromatic compounds in Salmonella typhimurium. Environ. Mol. Mutagen. 15, 44-55.
15. Maples, K. R., Eyer, P., and Mason, R. P. (1989). Aniline-, phenylhydroxylamine-, nitrosobenzene-, and nitrobenzene-induced hemoglobin thiyl free radical formation in vivo and in vitro. Mol. Pharmacol 37, 311-318.
16. O'Brien, P. J., Wong, W. C., Silva, J., and Khan, S. (1990). Toxicity of nitrobenzene compounds towards isolated hepatocytes: Dependence on reduction potential. Xenobiotica 20, 945-955.
17. Ortiz de Montellano, P. (1985). Cytochrome P-450, Structure, Mechanism and Biochemistry, Chapt. 11. Plenum Press, New York.
18. Piotrowski, J. (1967). Further investigations on the evaluation of exposure to nitrobenzene. Br. J. Ind. Med. 24, 60-65.
19. Reddy, B. G., Pohl, L. R., and Krishna, G. (1976). The requirement of the gut flora in nitrobenzene-induced methemoglobinemia in rats. Biochem. Pharmacol. 25, 1119-1122.
20. Rickert, D. E. (1987). Metabolism of nitro aromatic compounds. Drug. Metab. Rev. 18, 23-53.
21. Rickert, D. E., and Held, S. (1990). Metabolism of chloronitrobenzenes by isolated rat hepatocytes. Drug Metab. Disp. 18, 5-9.
22. Rietjens, I. M. C. M., Cnubben, N. H. P., van Haandel, M., Tyrakowska, B., Soffers, A. E. M. F., and Vervoort, J. (1995a). Different metabolic pathways of 2,5-difluoronitrobenzene and 2,5-difluoroaminobenzene compared to molecular orbital substrate characteristics. Chem. - Biol. Interact. 94, 49-72.
23. Rietjens, I. M. C. M., Soffers, A. E. M. F., Hooiveld, G., Veeger, C., and Vervoort, J. (1995b). 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.
24. Rietjens, I. M. C. M., Soffers, A. E. M. F., Veeger, C., and Vervoort, J. (1993). Regioselectivity of cytochrome P450 catalyzed hydroxylation of fluorobenzenes predicted by calculated frontier orbital substrate characteristics. Biochemistry 32, 4801-4812.
25. Sabbioni, G. (1992). Hemoglobin binding of monocyclic aromatic amines: Molecular dosimetry and quantitative structure activity relationships for the N-oxidation. Chem. - Biol. Interact. 81, 91-117.
26. Sabbioni, G. (1994). Hemoglobin binding of nitroarenes and quantitative structure - activity relationships. Chem. Res. Toxicol. 7, 267-274.
27. Shimizu, M., Yasui, Y., and Matsumoto, N. (1983). Structural specificity of aromatic compounds with special reference to mutagenic activity in Salmonella typhimurium - A series of chloro-or fluoro-nitrobenzene derivatives. Mut. Res. 116, 217-238.
28. Suzuki, J., Meguro, S., Moriat, O., Hirayama, S., and Suzuki, S. (1989). Comparison of in vivo binding of aromatic nitro and amino compounds to rat hemoglobin. Biochem. Pharmacol. 38, 3511-3519.
29. Tatsumi, K., Kitamura, S., Yoshimura, H., and Kawazoe, Y. (1978). Susceptibility of aromatic nitro compounds to xanthine oxidase-catalyzed reduction. Chem. Pharm. Bull. 26, 1713-1717.
30. 19F NMR method for studies on the in vivo and in vitro metabolism of 2-fluoroaniline. Xenobiotica 20, 657-670.
31. Vogel, A. J. (1978). Vogel's Textbook of Practical Organic Chemistry (B. S. Furniss, A. J. Hannaford, P. W. G. Smith, and A. R. Tatchell, Eds.), p. 684. Longman Scientific & Technical, London.
32. Yoshida, M., Yoshikawa, H., Goto, H., and Hara, I. (1989). Evaluation of the nephrotoxicity of aromatic nitro-amino compounds by urinary enzyme activities. J. Toxicol. Sci. 14, 257-268.