3-Amino-1,4-dimethyl-5H-pyridol[4,3-b]indole (Trp-P-1) triggers apoptosis by DNA double-strand breaks caused by inhibition of topoisomerase I

Carcinogenesis

Volumn 25, Issue 7, 2004, Pages 1149-1155

  Shiotani, Bunsyo ^a   Ashida, Hitoshi ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO 1,4 DIMETHYL 5H PYRIDO[4,3 B]INDOLE; 8 HYDROXYDEOXYGUANOSINE; CARCINOGEN; CASPASE 3; CASPASE 9; CYTOCHROME P450; CYTOCHROME P450 1A; CYTOCHROME P450 1B; DNA TOPOISOMERASE; DOUBLE STRANDED DNA; HISTONE H2A; HYDROXYAMINO ACID; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CARCINOGENESIS; CARCINOGENICITY; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DNA ADDUCT; DNA DAMAGE; DNA STRAND BREAKAGE; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INDUCTION; ENZYME INHIBITION; LIVER CELL; METABOLIC ACTIVATION; NONHUMAN; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION; RAT; WESTERN BLOTTING;

ANIMALS; APOPTOSIS; CARBOLINES; DEOXYGUANOSINE; DNA; DNA ADDUCTS; DNA TOPOISOMERASES, TYPE I; PHOSPHORYLATION; RATS; TIME FACTORS; TUMOR SUPPRESSOR PROTEIN P53;

EID: 3242759946     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/bgh112     Document Type: Article

References (39)

1. Matsukura,N., Kawachi,T., Morino,K., Ohgaki,H., Sugimura,T. and Takayama,S. (1981) Carcinogenicity in mice of mutagenic compounds from tryptophan pyrolysate. Science, 213, 346-347.
2. Ashida,H., Shiotani,B., Adachi,H., Hashimoto,T., Kanazawa,K. and Danno,G. (1998) Tryptophan pyrolysis products, Trp-P-1 and Trp-P-2 induce apoptosis in primary cultured rat hepatocytes. Biosci. Biotechnol. Biochem., 62, 2283-2287.
3. Shimada,T., Hayes,C.L., Yamazaki,H., Amin,S., Hecht,S.S., Guengerich,F.P. and Sutter,T.R. (1996) Activation of chemically diverse procarcinogens by human cytochrome P-450 1B1. Cancer Res., 56, 2979-2984.
4. Nagao,M., Takahashi,Y., Yahagi,T., Takeda,K., Shudo,K. and Okamoto,T. (1980) Mutagenicities of γ-carboline derivatives related to potent mutagens found in tryptophan pyrolysates. Carcinogenesis, 1, 451-454.
5. Mita,S., Yamazoe,Y., Kamataki,T. and Kato,R. (1983) Metabolic activation of Trp-P-2, a tryptophan-pyrolysis mutagen, by isolated rat hepatocytes. Biochem. Pharmacol., 32, 1179-1182.
6. Ishii,K., Ando,M., Kamataki,M., Kato,R. and Nagao,M. (1980) 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.
7. Oda,Y., Aryal,P., Terashita,T., Giliam,E.M., Guengerich,F.P. and Shimada,T. (2001) Metabolic activation of heterocyclic amines and other procarcinogens in Salmonella typhimurium umu tester strains expressing human cytochrome P4501A1, 1A2, 1B1, 2C9, 2D6, 2E1 and 3A4 and human NADPH-P450 reductase and bacterial O-acetyltransferase. Mutat. Res., 492, 81-90.
8. 32P-postlabelling analysis of DNA adducts formed in vivo by the parent amines and in vitro by their hydroxyamino derivatives. Mutagenesis, 3, 515-520.
9. Hashimoto,Y., Shudo,K. and Okamoto,T. (1980) Activation of a mutagen, 3-amino-1-methyl-5H-pyrido[4,3-b]indole. Identification of 3-hydroxyamino-1-methyl-5H-pyrido[4,3-b]indole and its reaction with DNA. Biochem. Biophys. Res. Common., 96, 355-362.
10. Hemminki,K. (1993) DNA adducts, mutations and cancer. Carcinogenesis, 14, 2007-2012.
11. Wakata,A., Oka,N., Hiramoto,K., Yoshioka,A., Negishi,K., Wataya,Y. and Hayatsu,H. (1985) 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.
12. Kasai,H. (1997) Analysis of a form of oxidative DNA damage, 8-hydroxy-2′-deoxyguanosine, as a marker of cellular oxidative stress during carcinogenesis. Mutat. Res., 387, 147-163.
13. Mori,T., Shimoi,K., Sasaki,Y.F., Wakabayashi,K., Nagao,M. and Kinae,N. (1993) 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1) inhibits the removal of both cyclobutane dimers and (6-4) photoproducts from the DNA of ultraviolet-irradiated E.coli. Carcinogenesis, 14, 1475-1478.
14. Funayama,Y., Nishio,K., Wakabayashi,K., Nagao,M., Shimoi,K., Ohira,T., Hasegawa,S. and Saijo,N. (1996) Effects of beta- and gamma-carboline derivatives of DNA topoisomerase activities. Mutat. Res., 349, 183-191.
15. Zhu,H., Boobis,A.R. and Gooderham,N.J. (2000) 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.
16. Rollet-Labelle,E., Grange,M.J., Elbim,C., Marquetty,C., Gougerot-Pocidalo,M.A. and Pasquier,C. (1998) Hydroxyl radical as a potential intracellular mediator of polymorphonuclear neutrophil apoptosis. Free. Radic. Biol. Med., 24, 563-572.
17. Tanaka,K., Pracyk,J.B., Takeda,K. et al. (1998) Expression of Id1 results in apoptosis of cardiac myocytes through a redox-dependent mechanism. J. Biol. Chem., 273, 25922-25928.
18. Kaufmann,S.H. (1998) Cell death induced by topoisomerase-targeted drugs: more questions than answers. Biochim. Biophys. Acta, 1400, 195-211.
19. Shiotani,B., Nonaka,Y., Hashimoto,T., Kihara,K., Kanazawa,K., Danno,G. and Ashida,H. (2001) 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.
20. Mosmann,T. (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assay. J. Immunol. Methods, 65, 55-63.
21. Darzynkiewicz,Z., Bruno,S., Del Bino,G., Gorczyca,W., Hotz,M.A., Lassota,P. and Traganos,F. (1992) Features of apoptotic cells measured by flow cytometry. Cytometry, 13, 795-808.
22. Gupta,R.C. (1984) Nonrandom binding of the carcinogen N-hydroxy-2-acetylamino-fluorene to repetitive sequences of rat liver DNA in vivo. Proc. Natl Acad. Sci. USA, 81, 6943-6947.
23. 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis, 7, 1543-1551.
24. 32P-postlabeling analysis of DNA adducts persisting for up to 42 weeks in the skin, epidermis and dermis of mice treated topically with 7,12-dimethylbenz[a]anthracene. Carcinogenesis, 6, 1117-1126.
25. Deffie,A.M., Batra,J.K. and Goldenberg,G.J. (1989) Direct correlation between DNA topoisomerase II activity and cytotoxicity in adriamycin-sensitive and -resistant P388 leukemia cell lines. Cancer Res., 49, 58-62.
26. Bradford,M.M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem., 72, 248-254.
27. Liu,L.F. (1989) DNA topoisomerase poisons as antitumor drugs. Annu. Rev. Biochem., 58, 351-375.
28. Shiotani,B., Nonaka,Y., Kanazawa,K., Danno,G. and Ashida,H. (2002) 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. Biosci. Biotechnol. Biochem., 63, 356-362.
29. Gerschenson,L.E., Andersson,M., Molson,J. and Okigaki,T. (1970) Tyrosine transaminase induction by dexamethasone in a new rat liver cell line. Science, 170, 859-861.
30. Shieh,S.Y., Ikeda,M., Taya,Y. and Prives,C. (1997) DNA damage-induced phosphorylation of p53 alleviates inhibition by MDM2. Cell, 91, 325-334.
31. Tibbetts,R.S., Brumbaugh,K.M., Williams,J.M., Sarkaria,J.N., Cliby,W.A., Shieh,S.Y., Taya,Y., Prives,C. and Abraham,R.T. (1999) A role for ATR in the DNA damage-induced phosphorylation of p53. Genes Dev., 13, 152-157.
32. Rogakou,E.P., Pilch,D.R., Orr,A.H., Ivanova,V.S. and Bonner,W.M. (1998) DNA double-stranded breaks induce histone H2AX phosphorylation on serine 139. J. Biol. Chem., 273, 5858-5868.
33. Levine,A.J. (1997) p53, the cellular gatekeeper for growth and division. Cell, 88, 323-331.
34. Ko,L.J. and Prives,C. (1996) p53: puzzle and paradigm. Genes Dev., 10, 1054-1072.
35. Sherr,C.J. and Roberts,J.M. (1995) Inhibitors of mammalian G1 cyclin-dependent kinases. Genes Dev., 9, 1149-1163.
36. Levine,A.J., Perry,M.E., Chang,A., Silver,A., Dittmer,D., Wu,M. and Welsh,D. (1994) The 1993 Walter Hubert Lecture: the role of the p53 tumor-suppressor gene in tumorigenesis. Br. J. Cancer, 69, 409-416.
37. Linke,S.P., Clarkin,K.C. and Wahl,G.M. (1997) p53 mediates permanent arrest over multiple cell cycles in response to gamma-irradiation. Cancer Res., 57, 1171-1179.
38. Jaks,V., Joers,A., Kristjuhan,A. and Maimets,T. (2001) p53 protein accumulation in addition to the transactivation activity is required for p53-dependent cell cycle arrest after treatment of cells with camptothecin. Oncogene, 20, 1212-1219.
39. 1 arrest in MCF-7 cells. Carcinogenesis, 21, 1611-1618.