Evoking cytochrome p450 1a activity interferes with apoptosis induced by 3-amino-1,4-dimethyl-5h-pyrido [4,3-b]indole (trp-p-1) in rat hepatocytes under the ex vivo system

Bioscience, Biotechnology and Biochemistry

Volumn 66, Issue 2, 2002, Pages 356-362

  Shiotani, Bunsyo ^a   Nonaka, Yuji ^a   Kanazawa, Kazuki ^a   Danno, Gen Ichi ^a   Ashida, Hitoshi ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

Apoptosis; Cytochrome P450; Hepatocytes; Heterocyclic amine; Trp P 1

Indexed keywords

3 AMINO 1,4 DIMETHYL 5H PYRIDO[4,3 B]INDOLE; CARBOLINE DERIVATIVE; CYTOCHROME P450; TRP-P-1;

ANIMAL; APOPTOSIS; ARTICLE; CYTOLOGY; DRUG EFFECT; ENZYME ACTIVATION; IN VITRO STUDY; LIVER CELL; MALE; METABOLISM; RAT; WISTAR RAT;

ANIMALS; APOPTOSIS; CARBOLINES; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME ACTIVATION; HEPATOCYTES; MALE; RATS; RATS, WISTAR;

EID: 0036479383     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.66.356     Document Type: Article

References (23)

1. Sugimura, T., Wakabayashi, K., Nagao, M., and Ohgaki, H., Heterocyclic amines in cooked food, In “Food toxicology, a perspective on the relative risks”, eds. Talor, S. L. and Scanlan, R. A., Dekker, New York, pp. 31-55 (1989).
2. Ishida, Y., Negishi, C., Umemoto, A., Fujita, Y., Sato, S., Sugimura, T., Thorgeirsson, S. S., and Adamson, R. H., Activation of mutagenic and carcinogenic heterocyclic amines by S-9 from liver of a rhesus monkey, Toxicol. In Vitro, 1, 45-48 (1987).
3. Nagao, M., Takahashi, Y., Yahagi, T., Takeda, K., Shudo, K., and Okamoto, T., Mutagenicities of g-carboline derivatives related to potent mutagens found in tryptophan pyrolysates, Carcinogenesis, 1, 451-454 (1980).
4. Mita, S., Yamazoe, Y., Kamataki, T., and Kato, R., Metabolic activation of Trp-P-2, a tryptophan-pyrol-ysis mutagen, by isolated rat hepatocytes, Biochem. Pharmacol, 32, 1179-1182 (1983).
5. Ishii, K., Ando, M., Kamataki, M., Kato, R., and Nagao, M., Metabolic activation of mutagenic tryptophan pyrolysis products (Trp-P-1 and Trp-P-2) by a purified cytochrome P450-dependent monooxygenase system, Cancer Lett., 9, 271-276 (1980).
6. Mita, S., Ishii, K., Yamazoe, Y., Kamatati, T., Kato, R., and Sugimura, T., Evidence for the involvement of N-hydroxylation of 2-amino-1-methyl-5 H-pyrido [4,3-b] indole by cytochrome P450 in the covalent binding to DNA, Cancer Res., 41, 3610-3614 (1981).
7. Shiotani, B., Nonaka, Y., Hashimoto, T., Kihara, K., Kanazawa, K., Danno, G., and Ashida, H., DNA-damaging carcinogen 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1) induces apoptosis via caspase-9 in primary cultured rat hepatocytes, Carcinogenesis, 22, 693-700 (2001).
8. Wakata, A., Oka, N., Hiramoto, K., Yoshioka, A., Negishi, K., Wataya, Y., and Hayatsu, H., DNA strand cleavage in vitro by 3-hydroxyamino-1-methyl-5H-pyrido[4,3-b]-indole, a direct-acting mutagen formed in the metabolism of carcinogenic 3-amino-1-methyl-5H-pyrido[4,3-b]indole. Cancer Res., 45, 5867-5871 (1985).
9. Ryan, D. E., Thomas, P. E., Korzeniowski, D., and Levin, W., Separation and characterization of highly purified forms of liver microsomal cytochrome P-450 from rats treated with polychlorinated biphenyls, phenobarbital, and 3-methylcholanthrene. J. Biol. Chem., 254, 1365-1374 (1979).
10. Waxman, D. J., and Azaroff, L., Phenobarbital induction of cytochrome P-450 gene expression, Biochem. J., 281, 577-592 (1992).
11. Kim, H., Putt, D., Reddy, S., Hollenberg, P. F., and Novak, R. F., Enhanced expression of rat hepatic CYP2B1 /2B2 and 2E1 by pyridine: differential induction kinetics and molecular basis of expression, J. Pharmacol. Exp. Ther., 267, 927-936 (1993).
12. Tanaka, K., Sato, M., Tomita, Y., and Ichihara, A., Biochemical studies on liver functions in primary cultured hepatocytes of adult rats. I. Hormonal effects on cell viability and protein synthesis, J. Biochem. Tokyo, 84, 937-946 (1978).
13. Mosmann, T., Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assay, J Immunol. Methods, 65, 55-63 (1983).
14. Burke, M. D., and Mayer, R. T., Differential effects of phenobarbitone and 3-methylcholanthrene induction on the hepatic microsomal metabolism and cytochrome P-450-binding of phenoxazone and a homologous series of its n-alkyl ethers (alkoxyresoru-fins), Chem. Biol. Interact., 45, 243-258 (1983).
15. Koop, D. R., Hydroxylation of p-nitrophenol by rabbit ethanol-inducible cytochrome P450 isozyme 3a, Mol. Pharmacol., 29, 399-404 (1986).
16. Jacobson, M., Levin, W., Poppers, P. J., Wood, A. W., and Conney, A. H., Comparison of the O-dealkylation of 7-ethoxycoumarin and the hydroxylation of benzo(a)pyrene in human placenta. Effect of cigarette smoking, Clin. Pharmacol. Ther., 16, 701-710 (1974).
17. Minamoto, S., and Kanazawa, K., Electrochemical determination for enzymatic production of ultimate carcinogen from tryptophan pyrolysate by rat hepatic microsomes. Analytical Biochemistry, 225, 143-148 (1995).
18. Ashida, H., Shiotani, B., Adachi, H., Hashimoto, T., Kanazawa, K., and Danno, G. Tryptophan pyrolysis products Trp-P-1 and Trp-P-2 induce apoptosis in primary cultured rat hepatocytes, Biosci. Biotechnol. Biochem., 62, 2283-2287 (1998).
19. Hashimoto, Y., Shudo, K., and Okamoto, T., Activation of a mutagen, 3-amino-1-methyl-5 H-pyrido[4,3-b]indole. Identification of 3-hydrox-yamino-1-methyl-5 H-pyrido[4,3-b]indole and its reaction with DNA, Biochem. Biophys. Res. Commun., 96, 355-362 (1980).
20. Zhu, H., Boobis, A. R., and Gooderham, N. J., The food-derived carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine activates S-phase checkpoint and apoptosis, and induces gene mutation in human lymphoblastoid TK6 cells, Cancer Res., 60, 1283-1289 (2000).
21. Scott, H. K., Cell death induced by topoisomerase-targeted drugs: more questions than answers. Biochim. Biophys. Acta, 1400, 195-211 (1998).
22. Funayama, Y., Nishio, K., Wakabayashi, K., Nagao, M., Shimoi, K., Ohira, T., Hasegawa, S., and Saijo, N., Effects of beta- and gamma-carboline derivatives of DNA topoisomerase activities. Mutat. Res., 349, 183-191 (1996).
23. Inohara, T., Tarui, M., Doi, M., Inoue, M., and Ishida, T., Interaction of mutagenic tryptophan pyrolysate with DNA. CD spectral study on the binding specificity. FEBS Lett., 324, 301-304 (1993).