Mechanism of oxidative DNA damage induced by δ-aminolevulinic acid in the presence of copper ion

Cancer Research

Volumn 56, Issue 8, 1996, Pages 1786-1793

  Hiraku, Yusuke ^a   Kawanishi, Shosuke ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b MIE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

8 HYDROXYDEOXYGUANOSINE; AMINOLEVULINIC ACID; COPPER ION; FREE RADICAL; LEAD; METAL ION; PYRAZINE DERIVATIVE;

ACUTE INTERMITTENT PORPHYRIA; ARTICLE; AUTOOXIDATION; CARCINOGENICITY; CONTROLLED STUDY; DNA DAMAGE; ELECTROCHEMICAL DETECTION; HEME SYNTHESIS; HUMAN; LEAD POISONING; LIVER CARCINOGENESIS; LIVER CARCINOMA; ONCOGENE C H RAS; PRIORITY JOURNAL;

AMINOLEVULINIC ACID; BASE SEQUENCE; CATALASE; COPPER; DEOXYGUANOSINE; DNA DAMAGE; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICAL SCAVENGERS; GENES, RAS; HYDROXYL RADICAL; MOLECULAR SEQUENCE DATA; OLIGODEOXYRIBONUCLEOTIDES; OXIDATION-REDUCTION; PHENANTHROLINES; PLASMIDS; RESTRICTION MAPPING;

EID: 0029871594     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (52)

1. IARC Working Group on the Evaluation of the Carcinogenic Risk of Chemicals to Man. Lead and lead compounds In IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, pp 230-232, Suppl 7 Lyon, France- IARC, 1987.
2. Boyland, E., Dukes, C. E., Grover, P L, and Mitchley, B. C. V. The induction of renal tumors by feeding lead acetate to rats Br. J. Cancer. 16: 283-288, 1962.
3. Oyasu, R., Battifora, H. A , Clasen, R. A , McDonald, J. H., and Hass, G. M. Induction of cerebral gliomas in rats with dietary lead subacetate and 2-acetylfluorene Cancer Res , 30: 1248-1261, 1970
4. Kobayashi, N , and Okamoto, T. Effects of lead oxide on the induction of lung tumors in Syrian hamsters J Natl Cancer Inst , 52: 1605-1610, 1974.
5. Muro, L. A., and Goyer, R. A. Chromosome damage in experimental lead poisoning. Arch Pathol., 87, 660-663, 1969.
6. Schwanitz, G., Gebhart, E., Rott, H. D., Schaller, K. H., Essing, H. G , Lauer, O., and Prestele, H. Chromosome investgations in subjects with occupational lead exposure. Dtsch. Med. Wochenschr., 100: 1007-1011, 1975.
7. Winder, C , and Bonin, T. The genotoxicity of lead, Mutat Res., 285: 117-124, 1993.
8. Selevan, S. G., Landrian, P. J., Stern, F B , and Jones, J H Mortality of lead smelter workers. Am. J. Epidemiol., 122, 673-683, 1985.
9. Cooper, W C., Wong, O . and Kheifets, L. Mortality among employees of lead battery, plants and lead-producing plants. 1947-1980 Scand J. Work Environ. Health, 11: 331-345, 1985
10. Gerhardsson, L , Lundstrom, N. G., Nordberg, G., and Wall, S. Mortality and lead exposure: a retrospective cohort study of Swedish smelter workers, Br. J Ind. Med., 43: 707-712, 1986.
11. Farkas, W. R., Fischbein, A., Solomon, S , Buschman, F , Borek, E., and Sharma, O. K. Elevated urinary excretion of β-aminoisobutyric acid and exposure to inorganic lead Arch. Environ Health. 42: 96-99, 1987.
12. Tomokuni, K., Ichiba, M , and Mon, K. Relation between urinary β-aminoisobutyric acid excretion and concentration of lead in the blood of workers occupationally exposed to lead Br J Ind. Med , 49: 365-368, 1992.
13. Kawanishi, S., Inoue, S , and Sano, S. Mechanism of DNA cleavage induced by sodium chromate(VI) in the presence of hydrogen peroxide. J. Biol. Chem., 261: 5952-5958, 1986
14. Inoue, S., and Kawanishi, S. Hydroxy radical production human DNA damage induced by ferric nitrilotriacetate hydrogen peroxide Cancer Res., 47: 6522-6527, 1987.
15. Yamamoto, K., Inoue, S., Yamazaki, A., Yoshinaga, T., and Kawanishi, S Site-specific DNA damage induced by cobalt(II) ion and hydrogen peroxide: role of singlet oxygen Chem. Res. Toxicol., 2: 234-239, 1989.
16. Kawanishi, S , Inoue, S , and Yamamoto, K Site-specific DNA damage induced by nickel(II) ion in the presence of hydrogen peroxide. Carcinogenesis (Lond.), 10: 2231-2235, 1989.
17. Inoue, S., and Kawanishi, S. ESR evidence for superoxide, hydroxyl radicals, and singlet oxygen produced from hydrogen peroxide and nickel(II) complex of gylcylgylcyl-L-histidine. Biochem. Biophys. Res. Commun., 159: 445-451, 1989.
18. Kawanishi, S., Inoue, S., and Yamamoto, K. Active oxygen species in DNA damage induced by carcinogenic metal compounds. Environ. Health Perspect., 102 (Suppl 3), 17-20, 1994.
19. Monteiro, H P , Abdalla, D. S P., Faljoni-Alário, A., and Bechara, E. J. H. Generation of active oxygen species during coupled autoxidation of oxyhemoglobin and δ-aminolevulinic acid. Biochim Biophys. Acta, 881: 100-106, 1986.
20. Monteiro, H. P , Abdalla, D. S. P., Augusto, O., and Bechara, E. J. H. Free radical generation during δ-aminolevulinic acid autoxidation induction by hemoglobin and connections with porphyrinpathies. Arch. Biochem. Biophys., 277: 206-216, 1989.
21. Ito, Y., Niiya, Y., Kurita, H., Shima, S., and Sarai, S. Serum lipid peroxide level and blood superoxide dismutase activity in workers with occupational exposure to lead. Int. Arch Occup. Environ. Health, 50: 119-128, 1985.
22. Monteiro, H P , Abdalla, D. S. P., Arcuni, A. S., and Bechara, E. J. H. Oxygen toxicity related to exposure to lead. Clin. Chem., 31, 1673-1676, 1985.
23. Medeiros, M. H G , Marchiori, P E., and Bechara, E J H Superoxide dismutase, glutathione peroxidase, and catalase activities in the erythrocytes of patients with intermittent acute porphyria Clin. Chem . 28: 242-243, 1982
24. Lithner, F., and Wetterberg, L. Hepatocellular carcinoma in patients with acute intermittent porphyria. Acta Med. Scand., 215: 271-274, 1984.
25. Kauppinen, R., and Mustajoki, P. Acute hepatic porphyria and hepatocellular carcinoma. Br. J. Cancer. 57: 117-120, 1988.
26. Yamamoto, K , and Kawanishi, S. 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, 1991.
27. Kawanishi, S., and Yamamoto, K Mechanism of site-specific DNA damage induced by methylhydrazines in the presence of copper(II) or manganese(III). Biochemistry, 30, 3069-3075, 1991
28. Capon, D. J., Chen, E Y., Levinson, A. D., Seeburg, P H., and Goeddel, D V. Complete nucleotide sequences of the T24 human bladder carcinoma oncogene and its normal homologue Nature (Lond.), 302: 33-37, 1983.
29. Maxam, A M., and Gilbert, W Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol , 65: 499-560, 1980.
30. Kasai, H , Crain, P. F., Kuchino, Y., Nishimura, S., Ootsuyama, A., and Tanooka, H. Formation of 8-hydroxyguanine moiety in cellular DNA by agents producing oxygen radicals and evidence for its repair. Carcinogenesis (Lond.), 7: 1849-1851, 1986.
31. Ito, K., Inoue, S., Yamamoto, K., and Kawanishi, S 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, 1993
32. Porra, R. J., Klein, O., Dornemann, D , and Senger, H. A simple method for the rapid determination of 4,5-dioxovaleric acid in the presence of 2-oxoglutarate and other 2-oxocarboxylic acids. Hoppe-Seyler's Z Physiol. Chem., 361, 187-190, 1980
33. Yamamoto, K., and Kawanishi, S. Hydroxyl free radical is not the main active species in site-specific DNA damage induced by copper(II) ion and hydrogen peroxide J. Biol. Chem., 264: 15435-15440, 1989.
34. Tkeshelashvili, L. K., McBride, T , Spence, K , and Loeb, L. A. Mutation spectrum of copper-induced DNA damage. J Biol. Chem., 266: 6401-6406, 1991
35. Aruoma, O. I., Halliwell, B., Gajewski, E , and Dizdaroglu, M. Copper-ion-dependent damage to the bases in DNA in the presence of hydrogen peroxide. Biochem J., 273: 601-604, 1991.
36. Yamamoto, K , and Kawanishi, S Site-specific DNA damage by phenylhydrazine and phenelzine in the presence of Cu(II) ion or Fe(III) complexes Roles of active oxygen species and carbon radicals Chem Res. Toxicol., 5: 440-446, 1992.
37. Oikawa, S., Kurasaki, M., Kojima, Y., and Kawanishi, S. Oxidative and nonoxidative mechanisms of site-specific DNA cleavage induced by copper-containing metallothioneins Biochemistry, 34: 8763-8770, 1995
38. Celander, D. W , and Cech, T R Iron(II)-ethylenediaminetetraacetic acid catalyzed cleavage of RNA and DNA oligonucleotides. Similar reactivity toward single- and double-stranded forms. Biochemistry, 29: 1355-1361, 1990
39. Dizdaroglu, M , Aruoma, O I , and Halliwell, B. Modification of bases in DNA by copper ion-1,10-phenanthroline complexes. Biochemistry, 29: 8447-8451, 1990.
40. Granick, S , and Mauzerall, D Porphyrin biosynthesis in erythrocytes II Enzymes converting δ-aminolevulinic acid to coproporphyrinogen. J. Biol. Chem., 232, 1119-1140, 1958.
41. Augusto, O., Cavalieri, E L., Rogan, E. G , RamaKrishna, N. V. S., and Kolar, C. Formation of 8-methylguanine as a result of DNA alkylation by methyl radicals generated during horseradish peroxidase-catalyzed oxidation of methlhydrazine. J Biol. Chem., 265: 22093-22096, 1990.
42. 2+ ions. Biochim. Biophys. Acta, 1225: 259-263, 1994.
43. Fraga, C. G., Onuki, J., Lucesoli, F., Bechara, E. J. H., and Di Mascio, P. 5-Aminolevulinic acid mediates the in vivo and in vitro formation of 8-hydroxy-2′-deoxyguanosine in DNA. Carcinogenesis (Lond.), 15: 2241-2244, 1994.
44. Dijkwel, P. A., and Wenink, P. W Structural integrity of the nuclear matrix: differential effects of thiol agents and metal chelators J. Cell. Sci., 84: 53-67, 1986.
45. Chiu, S , Xue, L., Friedman, L. R., and Oleinick, N. L. Differential dependence on chromatin structure for copper and iron ion induction of DNA double-stand breaks. Biochemistry, 34, 2653-2661, 1995
46. Guyton, K Z , and Kensler, T. W. Oxidative mechanisms in carcinogenesis. Br. Med Bull., 49: 523-544, 1993.
47. Kawanishi, S., Inoue, S., and Kawanishi, M. Human DNA damage induced by 1,2,4-benzenetriol, a benzene metabolite. Cancer Res., 49: 164-168, 1989
48. Inoue, S , Yamamoto, K., and Kawanishi, S DNA damage induced by metabolites of o-phenylphenol in the presence of copper(II) ion. Chem Res. Toxicol., 3: 144-149, 1990.
49. 2 formation. Carcinogenesis (Lond.), 13: 1497-1502, 1992.
50. Yamamoto, F., Kasai, H., Togashi, Y., Takeichi, N , Hori, T., and Nishimura, S. Elevated level of 8-hydroxydeoxyguanosine in DNA of liver, kidneys, and brain of Long-Evans Cinnamon rats. Jpn. J. Cancer Res., 84: 508-511, 1993.
51. Hindmarsh, J. T The porphyrias: recent advances. Clin. Chem., 32: 1255-1263, 1986.
52. Shibutani, S., Takeshita, M., and Grollman, A. P. Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Nature (Lond.), 349: 431-434, 1991.