Contribution of oxygen radicals to DNA cleavage by quinone compounds derived from phenolic antioxidants, tert-butylhydroquinone and 2,5-di-tert-butylhydroquinone

Toxicology Letters

Volumn 90, Issue 1, 1997, Pages 11-18

  Okubo, Tomoko ^a   Nagai, Fumiko ^a   Ushiyama, Keiko ^a   Kano, Itsu ^a  

^a TOKYO METROPOLITAN INSTITUTE OF PUBLIC HEALTH   (Japan)

Author keywords

2,5 Di tert butyl(1,4)hydroquinone; 2 tert Butyl(1,4)hydroquinone; 3 tert Butyl 4 hydroxyanisole; DNA cleavage; Oxygen radicals; Supercoiled DNA

Indexed keywords

2,5 DI TERT BUTYLHYDROQUINONE; ANTIOXIDANT; OXYGEN RADICAL; QUINONE DERIVATIVE; TERT BUTYLHYDROQUINONE;

ARTICLE; DNA CLEAVAGE; PRIORITY JOURNAL;

ANIMALS; ANTIOXIDANTS; BUTYLATED HYDROXYANISOLE; COPPER; CRICETINAE; DNA DAMAGE; FERROUS COMPOUNDS; FREE RADICALS; HYDROQUINONES; MESOCRICETUS; QUINONES; REACTIVE OXYGEN SPECIES;

EID: 0031031566     PISSN: 03784274     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-4274(96)03823-4     Document Type: Article

References (25)

1. Ito, N., Fukushima, S., Hagiwara, A., Shibata, M. and Ogiso, T. (1983) Carcinogenicity of butylated hydroxyanisole in F344 rats. J. Natl. Cancer Inst. 70, 343-352.
2. Altmann, H.-J., Wester, P.W., Matthiaschk, G., Grunow, W. and van der Heijden, C.A. (1985) Induction of early lesions in the forestomach of rats by 3-tert-butyl-4-hydroxyanisole (BHA). Food Chem. Toxicol. 23, 723-731.
3. Hirose, M., Masuda, A., Kurata, Y., Ikawa, E., Mera, Y. and Ito, N. (1986) Histologic and autoradiographic studies on the forestomach of hamsters treated with 2-tert-butylated hydroxyanisole, 3-tert-butylated hydroxyanisole, crude butylated hydroxyanisole, or butylated hydroxytoluene. J. Natl. Cancer Inst. 76, 143-149.
4. Verhagen, H., Schilderman, P.A.E.L. and Kleinjans, J.C.S. (1991) Butylated hydroxy-anisole in perspective. Chem.-Biol. Interact. 80, 109-134.
5. deStafney, C.M., Prabhu, U.D.G., Sparnins, V.L. and Wattenberg, L.W. (1986) Studies related to the mechanism of 3-BHA-induced neoplasia of the rat forestomach. Food Chem. Toxicol. 24, 1149-1157.
6. Astill, B.D., Mills, J., Rassett, R.L., Roundabush, R.L. and Terhaar, C.J. (1962) Fate of butylated hydroxyanisole in man and dog. Agric. Food Chem. 10, 315-318.
7. Verhagen, H., Thijssen, H.H.W., ten Hoor, F. and Kleinjans, J.C.S. (1989) Disposition of single oral doses of butylated hydroxyanisole in man and rat. Food Chem. Toxicol. 27, 151-158.
8. El-Rashidy, R. and Niazi, S. (1983) A new metabolite of butylated hydroxyanisole in man. Biopharm. Drug Dispos. 4, 389-396.
9. Armstrong, K.E. and Wattenberg, L.W. (1985) Metabolism of 3-tert-butyl-4-hydroxyanisole to 3-tert-butyl-4,5-dihydroxyanisole by rat liver microsomes. Cancer Res. 45, 1507-1510.
10. Giri, A.K., Sen, S., Talukder, G., Sharma, A. and Banerjee, T.S. (1984) Mutachromosomal effects of tert-butylhydroquinone in bone-marrow cells of mice. Food Chem. Toxicol. 22, 459-460.
11. Rogers, C.G., Boyes, B.G., Matula, T.I. and Stapley, R. (1992) Evaluation of genotoxicity of tert.-butylhydroquinone in an hepatocyte-mediated assay with V79 Chinese hamster lung cells and in strain D7 of Saccharomyces cerevisiae. Mutat. Res. 280, 17-27.
12. van Esch, G.J. (1986) Toxicology of tert-butylhydroquinone (TBHQ). Food Chem. Toxicol. 24, 1063-1065.
13. Hirose, M., Hagiwara, A., Inoue, K., Sakata, T., Ito, N., Kaneko, H., Yoshitake, A. and Miyamoto, J. (1987) Metabolism of 2-and 3-tert-butyl-4-hydroxyanisole (2-and 3-BHA) in the rat (I): excretion of BHA in urine, feces and expired air and distribution of BHA in the main organs. Toxicology 43, 139-147.
14. Lam, L.K.T. and Garg, P. (1991) Tumorigenicity of di-tert-butyl-substituted hydroquinone and hydroxyanisoles in the forestomach of Syrian golden hamsters. Carcinogenesis 12, 1341-1344,
15. Maniatis, T., Fritsch, E.F. and Sambrook, J. (1982) In: Molecular Cloning: A Laboratory Manual, Cold Spring Harbor Laboratory, New York, pp. 88-94.
16. MacCord, J.M. and Fridovich, I. (1969) Superoxide dismutase. An enzymatic function for erythrocuprein (hemo cuprein). J. Biol. Chem. 244, 6049-6055.
17. Nagai, F., Ushiyama, K., Satoh, K. and Kano, I. (1990) DNA cleavage by phenylhydroquinone: the major metabolite of a fungicide o-phenylphenol. Chem.-Biol. Interact. 76, 163-179.
18. Nagai, F., Ushiyama, K. and Kano, I. (1993) DNA cleavage by metabolites of butylated hydroxytoluene. Arch. Toxicol. 67, 552-557.
19. Li, Y. and Trush, M.A. (1993) DNA damage resulting from the oxidation of hydroquinone by copper: role for a Cu(II)/Cu(I) redox cycle and reactive oxygen generation. Carcinogenesis 14, 1303-1311.
20. Li, Y. and Trush, M.A. (1994) Reactive oxygen-dependent DNA damage resulting from the oxidation of phenolic compounds by a copper-redox cycle mechanism. Cancer Res. (Suppl.) 54, 1895s-1898s.
21. Li, Y., Kuppusamy, P., Zweier, J.L. and Trush, M.A. (1995) ESR evidence for the generation of reactive oxygen species from the copper-mediated oxidation of the benzene metabolite, hydroquinone: role in DNA damage. Chem.-Biol. Interact. 94, 101-120.
22. Kahl, R., Weinke, S. and Kappus, H. (1989) Production of reactive oxygen species due to metabolic activation of butylated hydroxyanisole. Toxicology 59, 179-194.
23. Schilderman, P.A.E.L., van Maanen, J.M.S., Smeets, E.J., ten Hoor, F. and Kleinjans, J.C.S. (1993) Oxygen radical formation during prostaglandin H synthase-mediated biotransformation of butylated hydroxyanisole. Carcinogenesis 14, 347-353.
24. Schilderman, P.A.E.L., van Maanen, J.M.S., ten Vaarwerk, F.J., Lafleur, M.V.M., Westmijze, E.J., ten Hoor, F. and Kleinjans, J.C.S. (1993) The role of prostaglandin H synthase-mediated metabolism in the induction of oxidative DNA damage by BHA metabolites. Carcinogenesis 14, 1297-1302.
25. Schilderman, P.A.E.L., ten Vaarwerk, F.J., Lutgerink, J.T., van der Wurff, A., ten Hoor, F. and Kleinjans, J.C.S. (1995) Induction of oxidative DNA damage and early lesions in rat gastro-intestinal epithelium in relation to prostaglandin H synthase-mediated metabolism of butylated hydroxyanisole. Food Chem. Toxicol. 33, 99-109.