N-acetylcysteine, a cancer chemopreventive agent, causes oxidative damage to cellular and isolated DNA

Carcinogenesis

Volumn 20, Issue 8, 1999, Pages 1485-1490

  Oikawa, Shinji ^a   Yamada, Keitaro ^a   Yamashita, Naruto ^a   Tada Oikawa, Saeko ^a   Kawanishi, Shosuke ^a  

^a MIE UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

8 HYDROXYDEOXYGUANOSINE; ACETYLCYSTEINE; ANTIOXIDANT; BATHOCUPROINE; CARCINOGEN; CATALASE; CELL DNA; CHELATING AGENT; COPPER ION; DEOXYRIBOSE; DNA FRAGMENT; GUANOSINE DERIVATIVE; HYDROGEN PEROXIDE; HYDROXYL RADICAL; PIPERIDINE; PROTEIN P53; SCAVENGER; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER PREVENTION; CARCINOGENESIS; CELL STRAIN HL 60; CONTROLLED STUDY; DNA DAMAGE; DRUG MECHANISM; DRUG SAFETY; HUMAN; HUMAN CELL; ISOTOPE LABELING; LEUKEMIA CELL LINE; ONCOGENE H RAS; PRIORITY JOURNAL; TUMOR SUPPRESSOR GENE;

ACETYLCYSTEINE; BIOLOGICAL MARKERS; COPPER; DEOXYGUANOSINE; DNA; DNA DAMAGE; FREE RADICAL SCAVENGERS; HL-60 CELLS; HUMANS; SEQUENCE ANALYSIS, DNA; TUMOR CELLS, CULTURED;

EID: 0032841575     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/20.8.1485     Document Type: Article

References (49)

1. Kelloff, G.J., Crowell, J.A., Boone, C.W., Steele, V.E., Lubet, R.A., Greenwald, P., Alberts, D.S., Covey, J.M., Doody, L.A., Knapp, G.G. et al. (1994) Clinical development plan: N-acetyl-L-cysteine. J. Cell. Biochem., 20 (suppl.), 63-73.
2. De Flora, S., D'Angostini, F., Izzotti, A. and Balansky, R. (1991) Prevention by N-acetylcysteine of benzo[a]pyrene clastogenicity and DNA adducts in rats. Mutat. Res., 250, 87-93.
3. De Flora, S., Izzotti, A., D'Angostini, F. and Cesarone, C.F. (1991) Antioxidant activity and other mechanisms of thiols involved in chemoprevention of mutation and cancer. Am. J. Med., 91, 122S-130S.
4. Balansky, R., Izzotti, A., Seatolini, L., D'Agostini, F. and De Flora, S. (1996) Induction by carcinogens and chemoprevention by N-acetylcysteine of adducts to mitochondrial DNA in rat organs. Cancer Res., 56, 1642-1647.
5. Izzotti, A., Bagnasco, M., Camoirano, A., Orlando, M. and De Flora, S. (1998) DNA fragmentation, DNA-protein crosslinks, postlabeled nucleotidic modifications, and 8-hydroxy-2′-deoxyguanosine in the lung but not in the liver of rats receiving intratracheal instillations of chromium(VI). Chemoprevention by oral N-acetylcysteine. Mutat. Res., 400, 233-244.
6. De Caro, L., Ghizzi, A., Costa, R., Longo, A., Ventresca, G.P. and Lodola, E. (1989) Pharmacokinetics and bioavailability of oral acetylcysteine in healthy volunteers. Arzneimittel-Forschung. Arzneim Forch/Drug Res., 39, 382-386.
7. De Flora, S., Balansky, R., Bennicelli, C., Camoirano, A., D'Agostini, F., Izzotti, A. and Cesarone, C.F. (1994) Mechanisms of anticarcinogenesis: The example of N-acetylcysteine. In Ioannides, C. (ed.) Drugs, Diet and Disease. Vol I: Mechanistic Approaches to Cancer. Prentice Hall, Herts, UK, pp. 151-203.
8. DeFlora, S., D'Agostini, F., Masielo, L., Giunciuglio, D. and Albini, A. (1996) Synergism between N-acetylcysteine and doxorubicin in the prevention of tumorigenicity and metastasis in murine models. Int. J. Cancer, 67, 842-848.
9. De Flora, S. and Ramel, C. (1988) Mechanisms of inhibitors of mutagenesis and carcinogenesis. Classification and overview. Mutat. Res., 202, 285-306.
10. De Flora, S., Cesarone, C.F., Balansky, R.M., Albini, A., D'Agostini, F., Bennicelli, C., Bagnasco, M., Camoirano, A., Scatolini, L., Rovida, A. et al. (1995) Chemopreventive properties and mechanisms of N-acetylcysteine. The experimental background. J. Cell. Biochem., 22 (suppl.), 33-41.
11. de Vries, N., Van Zonduijk, N. and Pastorino, U. (1991) The EUROSCAN Study. EUROSCAN Steering Committee. Br. J. Cancer, 64, 985-989.
12. Ponz de Leon, M. and Roncucci, L. (1997) Chemoprevention of colorectal tumors: role of lactulose and of other agents. Scand. J. Gastroenterol., 222 (suppl.), 72-75.
13. Halliwell, B., Murcia, M.A., Chirico, S. and Aruoma, O.I. (1995) Free radicals and antioxidants in food and In vivo: what they do and how they work. Crit. Rev. Food Sci. Nutr., 35, 7-20.
14. Diplock, A.T., Rice-Evans, C.A. and Burdon, R.H. (1994) Is there a significant role for lipid peroxidation in the causation of malignancy and for antioxidants in cancer prevention? Cancer Res., 54, 1952s-1956s.
15. The alpha-tocopherol, beta carotene cancer prevention study group (1994) The effect of vitamin E and beta carotene on the incidence of lung cancer and other cancers in male smokers. N. Engl. J. Med., 330, 1029-1035.
16. Omenn, G.S., Goodman, G.E., Thornquist, M.D., Balmes, J., Cullen, M.R., Glass, A., Keogh, J.P., Meyskens, F.L. Jr, Valanis, B., Williams, J.H. Jr, Barnhart, S., Cherniack, M.G., Brodkin, C.A. and Hammar, S. (1996) Risk factors for lung cancer and for intervention effects in CARET, the betacarotene and retinol efficacy trial. J. Natl Cancer Inst., 88, 1550-1559.
17. Shibutani, S., Takeshita, M. and Grollman, A.P. (1991) Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Nature, 349, 431-434.
18. Cheng, K.C, Cahill, D.S., Kasai, H., Nishimura, S. and Loeb, L.A. (1992) 8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G-T and A-C substitutions. J. Biol. Chem., 267, 166-172.
19. Kasugai, I. and Yamada, M. (1992) High production of catalase in hydrogen peroxide-resistant human leukemia HL-60 cell lines. Leukemia Res., 16, 173-179.
20. Ito, K., Inoue, S., Yamamoto, K. and Kawanishi, S. (1993) 8-Hydroxydeoxyguanosine formation at the 5′ site of 5′-GG-3′ sequences in double-stranded DNA by UV radiation with riboflavin. J. Biol. Chem., 268, 13221-13227.
21. Tada-Oikawa, S., Oikawa, S. and Kawanishi, S. (1998) Role of ultraviolet A-induced oxidative DNA damage in apoptosis via loss of mitochondrial membrane potential and caspase-3 activation. Biochem. Biophys. Res. Commun., 247, 693-696.
22. Chumakov, P. (1990) EMBL Data Library, accession number X54156.
23. Capon, D.J., Chen, E.Y., Levinson, A.D., Seeburg, P.H. and Goeddel, D.V. (1983) Complete nucleotide sequences of the T24 human bladder carcinoma oncogene and its normal homologue. Nature, 302, 33-37.
24. Yamashita, N., Murata, M., Inoue, S., Hiraku, Y., Yoshinaga, T. and Kawanishi, S. (1998) Superoxide formation and DNA damage induced by a fragrant furanone in the presence of copper(II). Mutal. Res., 397, 191-201.
25. Yamamoto, K. and Kawanishi, S. (1991) Site-specific DNA damage induced by hydrazine in the presence of manganese and copper ions: The role of hydroxyl radical and hydrogen atom. J. Biol. Chem., 266, 1509-1515.
26. Oikawa, S. and Kawanishi, S. (1996) Copper-mediated DNA damage by metabolites of p-dichlorobenzene. Carcinogenesis, 17, 2733-2739.
27. Maxam, A.M. and Gilbert, W. (1980) Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol., 65, 499-560.
28. Kasai, H., Nishimura, S., Kurosawa,Y. and Hayashi, Y. (1987) Oral administration of the renal carcinogen, potassium bromate, specifically produces 8-hydroxydeoxyguanosine in rat target organ DNA. Carcinogenesis, 8, 1959-1961.
29. Oikawa, S. and Kawanishi, S. (1988) Distinct mechanisms of site-specific DNA damage induced by endogeneous reductants in the presence of iron(III) and copper(II). Biochim. Biophys. Acta, 1399, 19-30.
30. Loft, S. and Poulsen, H.E. (1996) Cancer risk and oxidative DNA damage in man. J. Mol. Med., 74, 297-312.
31. Kawanishi, S., Inoue, S. and Sano, S. (1986) Mechanism of DNA cleavage induced by sodium chromate(VI) in the presence of hydrogen peroxide. J. Biol. Chem., 261, 5952-5958.
32. Celander, D.W. and Cech, T.R. (1990) Iron(II)-ethylenediaminetetraacetic acid catalyzed cleavage of RNA and DNA oligonucleotides: similar reactivity toward single-and double-stranded forms. Biochemistry, 29, 1355-1361.
33. Pryor, W.A. and Tang, R.H. (1978) Ethylene formation from methional. Biochem. Biophys. Res. Commun., 81, 498-503.
34. Dizdaroglu, M., Rao, G., Halliwell, B. and Gajewski, E. (1991) Damage to the DNA bases in mammalian chromatin by hydrogen peroxide in the presence of ferric and cupric ions. Arch. Biochem. Biophys., 285, 317-324.
35. Dijkwel, P.A. and Wenink, P.W. (1986) Structural integrity of the nuclear matrix: differential effects of thiol agents and metal chelators. J. Cell. Sci., 84, 53-67.
36. Oikawa, S., Kurasaki, M., Kojima, Y. and Kawanishi, S. (1995) Oxidative and nonoxidative mechanisms of site-specific DNA cleavage induced by copper-containing metallothioneins. Biochemistry, 34, 8763-8770.
37. Chiu, S., Xue, L., Friedman, L.R. and Oleinick, N.L. (1995) Differential dependence on chromatin structure for copper and iron ion induction of DNA double-strand breaks. Biochemistry, 34, 2653-2661.
38. ikawa,S. and Kawanishi, S. (1996) Site-specific DNA damage induced by NADH in the presence of copper(II): role of active oxygen species. Biochemistry, 35, 4584-4590.
39. Badr, F.M., El-Habit, O.H., Hamdy, M. and Hassan, G.A. (1998) The mutagenic versus protective role of vitamin A on the induction of chromosomal aberration in human lymphocyte cultures. Mutat. Res., 414, 157-163.
40. Kurokawa, Y., Hayashi, Y., Maekawa, ., Takahashi, M. and Kukubo.T. (1985) High incidences of pheochromocytomas after long-term administration of retinol acetate to F344/DuCrj rats. J. Natl Cancer Inst., 74, 715-723.
41. Nitta, Y., Kamiya, K., Tanimoto, M., Sadamoto, S., Niwa, O. and Yokoro, K. (1991) Induction of transplantable tumors by repeated subcutaneous injections of natural and synthetic vitamin E in mice and rats. Jpn J. Cancer Res., 82, 511-517.
42. Mitchel, R.E.J. and McCann, R. (1993) Vitamin E is a complete tumor promotor in mouse skin. Carcinogenesis, 14, 659-622.
43. Temple, N.J. and El-Khatib, S.M. (1987) Cabbage and vitamin E: their effect on colon tumor formation in mice. Cancer Lett., 35, 71-77.
44. Kline, K and Sanders, B.G. (1989) Modulation of immune suppression and enhanced tumorigenesis in retrovirus tumor challenged chickens treated with vitamin E. In Vivo, 3, 161-166.
45. Yamashita, N., Murata, M., Inoue, S., Burkitt, M.J., Milene, L. and Kawanishi, S. (1998) α-Tocopherol induces oxidative damage to DNA in the presence of copper(II) ions. Chem. Res. Toxicol, 11, 855-862.
46. de Vries, N., Pastorino, U. and van Zandwijk, N. (1994) Chemoprevention of second primary tumours in head and neck cancer in Europe: EUROSCAN. Eur. J. Cancer. Part B, Oral Oncology, 30B, 367-368.
47. 32P post-labeling. Free Rad. Res., 28, 165-178.
48. 2 formation. Carcinogenesis, 13, 1497-1502.
49. Sprong, R.C, Winkelhuyzen-Janssen, A.M., Aarsman, C.J., van Oirschot, J.F., van der Bruggen, T. and van Asbeck, B.S. (1998) Low-dose N-acetylcysteine protects rats against endotoxin-mediated oxidative stress, but high-dose increases mortality. Am. J. Resp. Crit. Care Med., 157, 1283-1293.