Formation of nitrated and hydroxylated aromatic compounds from benzene and peroxynitrite, a possible mechanism of benzene genotoxicity

Free Radical Research

Volumn 28, Issue 4, 1998, Pages 369-375

  Tuo, Jingsheng ^a   Wolff, Simon P ^b   Loft, Steffen ^a   Poulsen, Henrik E ^a,c  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b ROYAL FREE AND UNIVERSITY COLLEGE MEDICAL SCHOOL   (United Kingdom)

^c University of Copenhagen   (Denmark)

Author keywords

Benzene; Hydroxylation; Neutrophils; Nitration; Peroxynitrite

Indexed keywords

ANTIINFLAMMATORY AGENT; AROMATIC COMPOUND; BENZENE; NITRIC OXIDE; NITROBENZENE; NITROPHENOL; PEROXYNITRITE; PHENOL; PHORBOL 13 ACETATE 12 MYRISTATE; SUPEROXIDE;

ARTICLE; BONE MARROW TOXICITY; CANCER RISK; CARCINOGENICITY; CELL ACTIVATION; CHEMICAL REACTION; GENOTOXICITY; HYDROXYLATION; IMMUNE RESPONSE; INFECTION; INFLAMMATORY CELL; NEUTROPHIL; NITRATION;

EID: 0031821387     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.3109/10715769809070805     Document Type: Article

References (41)

1. V. V. Subrahmanyam, D. Ross, D. A. Eastmond and M. T. Smith (1991) Potential role of free radicals in benzene-induced myelotoxicity and leukemia. Free Radical Biology & Medicine, 11, 495-515.
2. R. A. Rinsky, A. B. Smith, R. Hornung, T. G. Filloon, R. J. Young, A. H. Okun and P. J. Landrigan (1987) Benzene and leukemia. An epidemiologic risk assessment. New England Journal of Medicine, 316, 1044-1050.
3. H. Austin, E. Delzell and P. Cole (1988) Benzene and leukemia. A review of the literature and a risk assessment. American Journal of Epidemiology, 127, 419-439.
4. M. Aksoy (1989) Hematotoxicity and carcinogenicity of benzene. Environmental Health Perspectives, 82, 193-197.
5. J. E. Huff, J. K. Haseman, D. M. DeMarini, S. Eustis, R. R. Maronpot, A. C. Peters, R. L. Persing, C. E. Chrisp and A. C. Jacobs (1989) Multiple-site carcinogenicity of benzene in Fischer 344 rats and B6C3F1 mice. Environmental Health Perspectives, 82, 125-163.
6. G. F. Kalf (1987) Recent advances in the metabolism and toxicity of benzene. Critical Reviews in Toxicology, 18, 141-159.
7. M. J. Seaton, P. M. Schlosser, J. A. Bond and M. A. Medinsky (1994) Benzene metabolism by human liver microsomes in relation to cytochrome P450 2E1 activity. Carcinogenesis, 15, 1799-1806.
8. L. M. Gonasun, C. Witmer, J. J. Kocsis and R. Snyder (1970) Benzene metabolism in mouse liver microsomes. Toxicology & Applied Pharmacology, 26, 398-406.
9. D. E. Rickert, T. S. Baker, J. S. Bus, C. S. Barrow and R. D. Irons (1979) Benzene disposition in the rat after exposure by inhalation. Toxicology & Applied Pharmacology, 49, 417-423.
10. M. M. Gad-el-Karim, V. M. Ramanujam, A. E. Ahmed and M. S. Legator (1985) Benzene myeloclastogenicity: a function of its metabolism. American Journal of Industrial Medicine, 7, 475-484.
11. J. Tuo, S. Loft, M. S. Thomsen and H. E. Poulsen (1996) Benzene-induced genotoxicity in mice in vivo detected by the alkaline comet assay: reduction by CYP2E1 inhibition. Mutation Research, 368, 213-219.
12. M. Dosemeci, A. Blair, P. A. Stewart, J. Chandler and M. A. Trush (1991) Mortality among industrial workers exposed to phenol. Epidemiology, 2, 188-193.
13. National Toxicology Program (NTP) (1980): Bioassay of phenol for possible carcinogenicity, NCI/NTP, Bethesda, MD.
14. National Toxicology Program (NTP) (1986): Toxicology and carcinogenesis studies of benzene (CAS No. 71-43-2) in F344/N rats and B6C3F1 mice (gavage studies), NTP, Bethesda, MD. p. 1036.
15. International agency for research on cancer (IARC) (1982): Some industrial chemicals and dyestuffs. IARC monograghs on the evaluation of the carcinogenic risk of chemicals to humans. Vol. 29. IAC, Lyon. pp. 93-148.
16. International agency for research on cancer (IARC) (1988): Environmental carcinogens-methods of analysis and exposure measurement, benzene and alkylated benzene. Vol. 10. IARC, Lyon. pp. 3-18.
17. •-. implications for the action of endothelium-derived relaxing factor (EDRF). Free Radical Research Communications, 10, 221-226.
18. C. J. Punjabi, D. L. Laskin, D. E. Heck and J. D. Laskin (1992) Production of nitric oxide by murine bone marrow cells. Inverse correlation with cellular proliferation. Journal of Immunology, 149, 2179-2184.
19. C. J. Punjabi, J. D. Laskin, S. M. Hwang, L. MacEachern and D. L. Laskin (1994) Enhanced production of nitric oxide by bone marrow cells and increased sensitivity to macrophage colony-stimulating factor (CSF) and granulocyte-macrophage CSF after benzene treatment of mice. Blood, 83, 3255-3263.
20. N. R. Rao and R. Snyder (1995) Oxidative modifications produced in HL-60 cells on exposure to benzene metabolites. Journal of Applied Toxicology, 15, 403-409.
21. J. S. Beckman, T. W. Beckman, J. Chen, P. A. Marshall and B. A. Freeman (1990) Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide. Proceedings of the National Academy of Sciences of the United States of America, 87, 1620-1624.
22. T. Utsumi, J. Klostergaard, K. Akimaru, K. Edashige, E. F. Sato and K. Utsumi (1992) Modulation of TNF-alpha-priming and stimulation-dependent superoxide generation in human neutrophils by protein kinase inhibitors. Archives of Biochemistry & Biophysics, 294, 271-278.
23. E. Prigmore, S. Ahmed, A. Best, R. Kozma, E. Manser, A. W. Segal and L. Lim (1995) A 68-kDa kinase and NADPH oxidase component p67phox are targets for Cdc42Hs and Racl in neutrophils. Journal of Biological Chemistry, 270, 10717-10722.
24. N. Fukuyama, K. Ichimori, Z. Su, H. Ishida and H. Nakazawa (1996) Peroxynitrite formation from activated human leukocytes. Biochemical & Biophysical Research Communications, 224, 414-419.
25. J. P. Eiserich, C. E. Cross, A. D. Jones, B. Halliwell and A. van der Vliet (1996) Formation of nitrating and chlorinating species by reaction of nitrite with hypochlorous acid. A novel mechanism for nitric oxidemediated protein modification. Journal of Biological Chemistry, 271, 19199-19208.
26. D. C. Mays, L. J. Pawluk, G. Apseloff, W. B. Davis, Z. W. She, A. L. Sagone and N. Gerber (1995) Metabolism of phenytoin and covalent binding of reactive intermediates in activated human neutrophils. Biochemical Pharmacology, 50, 367-380.
27. W. B. Davis, B. S. Mohammed, D. C. Mays, Z. W. She, J. R. Mohammed, R. M. Husney and A. L. Sagone (1989) Hydroxylation of salicylate by activated neutrophils. Biochemical Pharmacology, 38, 4013-4019.
28. A. J. Kettle and C. C. Winterbourn (1994) Superoxide-dependent hydroxylation by myeloperoxidase. Journal of Biological Chemistry, 269, 17146-17151.
29. D. L. Laskin, L. MacEachern and R. Snyder (1989) Activation of bone marrow phagocytes following benzene treatment of mice. Environmental Health Perspectives, 82, 75-79.
30. L. MacEachern, R. Snyder and D. L. Laskin (1992) Alterations in the morphology and functional activity of bone marrow phagocytes following benzene treatment of mice. Toxicology & Applied Pharmacology, 117, 147-154.
31. L. MacEachern and D. L. Laskin (1992) Increased production of tumor necrosis factor-alpha by bone marrow leukocytes following benzene treatment of mice. Toxicology & Applied Pharmacology, 113, 260-266.
32. R. Snyder and C. C. Hedli (1996) An overview of benzene metabolism. Environmental Health Perspectives, 104 (suppl. 6), 1165-1171.
33. A. van der Vliet, C. A. O'Neill, B. Halliwell, C. E. Cross and H. Kaur (1994) Aromatic hydroxylation and nitration of phenylalanine and tyrosine by peroxynitrite. Evidence for hydroxyl radical production from peroxynitrite. FEBS Letters, 339, 89-92.
34. H. Ischiropoulos, L. Zhu, J. Chen, M. Tsai, J. C. Martin, C. D. Smith and J. S. Beckman (1992) Peroxynitrite-mediated tyrosine nitration catalyzed by superoxide dismutase. Archives of Biochemistry & Biophysics, 298, 431-437.
35. H. Kaur, M. Whiteman and B. Halliwell (1997) Peroxynitrite-dependent aromatic hydroxylation and nitration of salicylate and phenylalanine. Is hydroxyl radical involved? Free Radical Research, 26, 71-82.
36. M. S. Ramezanian, S. Padmaja and W. H. Koppenol (1996) Nitration and hydroxylation of phenolic compounds by peroxynitrite. Chemical Research in Toxicology, 9, 232-240.
37. K. T. Chung, C. A. Murdock, Y. Zhou, S. E. Stevens, Jr., Y. S. Li, C. I. Wei, S. Y. Fernando and M. W. Chou (1996) Effects of the nitro-group on the mutagenicity and toxicity of some benzamines. Environmental & Molecular Mutagenesis, 27, 67-74.
38. K. T. Chung, C. A. Murdock, S. E. Stevens, Jr., Y. S. Li, C. I. Wei, T. S. Huang and M. W. Chou (1995) Mutagenicity and toxicity studies of p-phenylenediamine and its derivatives. Toxicology Letters, 81, 23-32.
39. K. T. Chung and C. E. Cerniglia (1992) Mutagenicity of azo dyes: structure-activity relationships. Mutation Research, 277, 201-220.
40. M. Shimizu, Y. Yasui and N. Matsumoto (1983) Structural specificity of aromatic compounds with special reference to mutagenic activity in Salmonella typhimurium - a series of chloro- or fluoro-nitrobenzene derivatives. Mutation Research, 116, 217-238.
41. M. Shimizu and E. Yano (1986) Mutagenicity of mono-nitrobenzene derivatives in the Ames test and rec assay. Mutation Research, 170, 11-22.