Molecular mechanisms of DNA damage induced by procarbazine in the presence of Cu(II)

Mutation Research - Genetic Toxicology and Environmental Mutagenesis

Volumn 539, Issue 1-2, 2003, Pages 145-155

  Ogawa, Kazuhiko ^a   Hiraku, Yusuke ^a   Oikawa, Shinji ^a   Murata, Mariko ^a   Sugimura, Yoshiki ^a   Kawamura, Juichi ^a   Kawanishi, Shosuke ^a  

^a MIE UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

8 Oxo 7,8 dihydro 2 deoxyguanosine; Copper; DNA damage; Hydrogen peroxide; Methyl radicals; Procarbazine

Indexed keywords

8 HYDROXYDEOXYGUANOSINE; CATALASE; COPPER; DNA FRAGMENT; HYDROGEN PEROXIDE; METHYL GROUP; PIPERIDINE; PROCARBAZINE; PROTEIN P53; PYRIMIDINE DERIVATIVE;

ARTICLE; CARCINOGENESIS; CARCINOGENIC ACTIVITY; DNA DAMAGE; DNA SEQUENCE; ELECTRON SPIN RESONANCE; MUTAGENESIS; PRIORITY JOURNAL; PROTO ONCOGENE; TUMOR SUPPRESSOR GENE;

ANIMALIA;

EID: 0042388508     PISSN: 13835718     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1383-5718(03)00157-8     Document Type: Article

References (62)

1. Ito K., Yamamoto K., Kawanishi S. Manganese-mediated oxidative damage of cellular and isolated DNA by isoniazid and related hydrazines: non-Fenton-type hydroxyl radical formation. Biochemistry. 31:1992;11606-11613.
2. Toth B. Synthetic and naturally occurring hydrazines as possible cancer causative agents. Cancer Res. 35:1975;3693-3697.
3. Parodi S., De Flora S., Cavanna M., Pino A., Robbiano L., Bennicelli C., Brambilla G. DNA-damaging activity in vivo and bacterial mutagenicity of sixteen hydrazine derivatives as related quantitatively to their carcinogenicity. Cancer Res. 41:1981;1469-1482.
4. Weekes C.D., Vose J.M., Lynch J.C., Weisenburger D.D., Bierman P.J., Greiner T., Bociek G., Enke C., Bast M., Chan W.C., Armitage J.O. Hodgkin's disease in the elderly: improved treatment outcome with a doxorubicin-containing regimen. J. Clin. Oncol. 20:2002;1087-1093.
5. Travis L.B., Gospodarowicz M., Curtis R.E., Clarke E.A., Andersson M., Glimelius B., Joensuu T., Lynch C.F., van Leeuwen F.E., Holowaty E., Storm H., Glimelius I., Pukkala E., Stovall M., Fraumeni J.F. Jr., Boice J.D. Jr., Gilbert E. Lung cancer following chemotherapy and radiotherapy for Hodgkin's disease. J. Natl. Cancer Inst. 94:2002;182-192.
6. 6-methylguanine. Carcinogenesis. 18:1997;2191-2196.
7. Haseman J.K., Hailey J.R. An update of the National Toxicology Program database on nasal carcinogens. Mutat. Res. 380:1997;3-11.
8. Bacci M., Cavaliere A., Fratini D. Lung carcinogenesis by procarbazine chlorate in BALB/c mice. Carcinogenesis. 3:1982;71-73.
9. Suzuki T., Uno Y., Idehara K., Baba T., Maniwa J., Ohkouchi A., Wang X., Hayashi M., Sofuni T., Tsuruoka M., Miyajima H., Kondo K. Procarbazine genotoxicity in the Muta™ mouse; strong clastogenicity and organ-specific induction of lacZ mutation. Mutat. Res. 444:1999;269-281.
10. Swerdlow A.J., Schoemaker M.J., Allerton R., Horwich A., Barber J.A., Cunningham D., Lister T.A., Rohatiner A.Z., Vaughan Hudson G., Williams M.V., Linch D.C. Lung cancer after Hodgkin's disease: a nested case-control study of the relation to treatment. J. Clin. Oncol. 19:2001;1610-1618.
11. Delwail V., Jais J.P., Colonna P., Andrieu J.M. Fifteen-year secondary leukaemia risk observed in 761 patients with Hodgkin's disease prospectively treated by MOPP or ABVD chemotherapy plus high-dose irradiation. Br. J. Haematol. 118:2002;189-194.
12. Aisenberg A.C. Problems in Hodgkin's disease management. Blood. 93:1999;761-779.
13. Greil R. Prognosis and management strategies of lymphatic neoplasias in the elderly. II. Hodgkin's disease. Oncology. 55:1998;265-275.
14. IARC Working Group, Some industrial chemicals and dyestuffs, in: IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, vol. 26, IARC, Lyon, 1981, pp. 311-339.
15. IARC Working Group, Procarbazine hydrochloride, in: IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs 1-42, Suppl. 7, IARC, Lyon, 1987, p. 327.
16. Sinha B.K. Metabolic activation of procarbazine. Biochem. Pharmacol. 33:1984;2777-2781.
17. Augusto O., Cavalieri E.L., Rogan E.G., RamaKrishna N.V., Kolar C. Formation of 8-methylguanine as a result of DNA alkylation by methyl radicals generated during horseradish peroxidase-catalyzed oxidation of methylhydrazine. J. Biol. Chem. 265:1990;22093-22096.
18. Horstman M.G., Meadows G.G., Yost G.S. Separate mechanisms for procarbazine spermatotoxocity and anticancer activity. Cancer Res. 47:1987;1547-1550.
19. Kasai H., Chung M.H., Jones D., Inoue H., Ishikawa H., Kamiya H., Ohtsuka E., Nishimura S. 8-Hydroxyguanine, a DNA adduct formed by oxygen radicals: its implication on oxygen radical-involved mutagenesis/carcinogenesis. J. Toxicol. Sci. 16(Suppl. 1):1991;95-105.
20. P. Chumakov, EMBL Data Library, Accession number X54156 , 1990.
21. Capon D.J., Chen E.Y., Levinson A.D., Seeburg P.H., Goeddel D.V. Complete nucleotide sequences of the T24 human bladder carcinoma oncogene and its normal homologue. Nature. 302:1983;33-37.
22. Yamashita N., Murata M., Inoue S., Hiraku Y., Yoshinaga T., Kawanishi S. Superoxide formation and DNA damage induced by a fragrant furanone in the presence of copper(II). Mutat. Res. 397:1998;191-201.
23. Yamamoto K., 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. 266:1991;1509-1515.
24. Maxam A.M., Gilbert W. Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol. 65:1980;499-560.
25. Kasai H., Crain P.F., Kuchino Y., Nishimura S., Ootsuyama A., Tanooka H. Formation of 8-hydroxyguanine moiety in cellular DNA by agents producing oxygen radicals and evidence for its repair. Carcinogenesis. 7:1986;1849-1851.
26. Ito K., Inoue S., Yamamoto K., Kawanishi S. 8-Hydroxydeoxyguanosine formation at the 5′ site of 5′-GG-3′ sequences in double-stranded DNA by UV radiation with riboflavine. J. Biol. Chem. 268:1993;13221-13227.
27. Yamashita N., Murata M., Inoue S., Burkitt M.J., Milne L., Kawanishi S. α-Tocopherol induces oxidative damage to DNA in the presence of copper(II) ions. Chem. Res. Toxicol. 11:1998;855-862.
28. Buettner G.R. Spin trapping: ESR parameters of spin adducts. Free Radical Biol. Med. 3:1987;259-303.
29. David-Cordonnier M.H., Laval J., O'Neill P. Clustered DNA damage, influence on damage excision by XRS5 nuclear extracts and Escherichia coli Nth and Fpg proteins. J. Biol. Chem. 275:2000;11865-11873.
30. Boiteux S., Gajewskim E., Laval J., Dizdaroglu M. Substrate specificity of the Escherichia coli Fpg protein (formamidopyrimidine-DNA glycosylase): excision of purine lesions in DNA produced by ionizing radiation or photosensitization. Biochemistry. 31:1992;106-110.
31. Bruner S.D., Norman D.P., Verdine G.L. Structural basis for recognition and repair of the endogenous mutagen 8-oxoguanine in DNA. Nature. 403:2000;859-866.
32. Box H.C., Dawidzik J.B., Budzinski E.E. Free radical-induced double lesions in DNA. Free Radical Biol. Med. 31:2001;856-868.
33. Bourdat A.G., Douki T., Frelon S., Gasparutto D., Cadet J. Tandem base lesions are generated by hydroxyl radical within isolated DNA in aerated aqueous solution. J. Am. Chem. Soc. 122:2000;4549-4556.
34. Ohnishi S., Kawanishi S. Double base lesions of DNA by a metabolite of carcinogenic benzo[a]pyrene. Biochem. Biophys. Res. Commun. 290:2002;778-782.
35. Blaisdell J.O., Wallace S.S. Abortive base-excision repair of radiation-induced clustered DNA lesions in Escherichia coli. Proc. Natl. Acad. Sci. U.S.A. 98:2001;7426-7430.
36. Kawanishi S., Inoue S., Sano S. Mechanism of DNA cleavage induced by sodium chromate(VI) in the presence of hydrogen peroxide. J. Biol. Chem. 261:1986;5952-5958.
37. Celander D.W., Cech T.R. Iron(II)-ethylenediaminetetraacetic acid catalyzed cleavage of RNA and DNA oligonucleotides: similar reactivity toward single- and double-stranded forms. Biochemistry. 29:1990;1355-1361.
38. Rao P.S., Luber J.M. Jr., Milinowicz J., Lalezari P., Muller H.S. Specificity of oxygen radical scavengers and assessment of free radical scavenger efficiency using luminol enhanced chemiluminescence. Biochem. Biophys. Res. Commun. 150:1988;39-44.
39. Youngman R.J., Elstner E.F. Oxygen species in paraquat toxicity: the crypto-OH radical. FEBS Lett. 129:1981;265-268.
40. Pryor W.A., Tang R.H. Ethylene formation from methional. Biochem. Biophys. Res. Commun. 81:1978;498-503.
41. Dizdaroglu M., Aruoma O.I., Halliwell B. Modification of bases in DNA by copper ion-1,10-phenanthroline complexes. Biochemistry. 29:1990;8447-8451.
42. Midorikawa K., Hirakawa K., Kawanishi S. Hydroxylation of deoxyguanosine at 5′ site of GG and GGG sequences in double-stranded DNA induced by carbamoyl radicals. Free Radical Res. 36:2002;667-675.
43. Hiramoto K., Kaku M., Kato T., Kikugawa K. DNA strand breaking by the carbon-centered radical generated from 4-(hydroxymethyl) benzenediazonium salt, a carcinogen in mushroom Agaricus bisporus. Chem. Biol. Interact. 94:1995;21-36.
44. Hiramoto K., Kaku M., Sueyoshi A., Fujise M., Kikugawa K. DNA base and deoxyribose modification by the carbon-centered radical generated from 4-(hydroxymethyl)benzenediazonium salt, a carcinogen in mushroom. Chem. Res. Toxicol. 8:1995;356-362.
45. Adam W., Arnold M.A., Nau W.M., Pischel U., Saha-Moller C.R. A comparative photomechanistic study (spin trapping, EPR spectroscopy, transient kinetics, photoproducts) of nucleoside oxidation (dG and 8-oxodG) by triplet-excited acetophenones and by the radicals generated from α-oxy-substituted derivatives through Norrish-type I cleavage. J. Am. Chem. Soc. 124:2002;3893-3904.
46. 2-induced DNA damage and alter its site specificity. FEBS Lett. 495:2001;187-190.
47. Ohkuma Y., Kawanishi S. Oxidative DNA damage induced by a metabolite of carcinogenic o-anisidine: enhancement of DNA damage and alteration in its sequence specificity by superoxide dismutase. Arch. Biochem. Biophys. 389:2001;49-56.
48. Burkitt M.J. Copper-DNA adducts. Methods Enzymol. 234:1994;66-79.
49. Theophanides T., Anastassopoulou J. Copper and carcinogenesis. Crit. Rev. Oncol. Hematol. 42:2002;57-64.
50. Obata H., Sawada N., Isomura H., Mori M. Abnormal accumulation of copper in LEC rat liver induces expression of p53 and nuclear matrix-bound p21(waf 1/cip 1). Carcinogenesis. 17:1996;2157-2161.
51. Kitaura K., Chone Y., Satake N., Akagi A., Ohnishi T., Suzuki Y., Izumi K. Role of copper accumulation in spontaneous renal carcinogenesis in Long-Evans Cinnamon rats. Jpn. J. Cancer Res. 90:1999;385-392.
52. Bartsch H., Nair J. Ultrasensitive and specific detection methods for exocylic DNA adducts: markers for lipid peroxidation and oxidative stress. Toxicology. 153:2000;105-114.
53. Linder M.C. Copper and genomic stability in mammals. Mutat. Res. 475:2001;141-152.
54. 6-methylguanine. Carcinogenesis. 18:1997;2191-2196.
55. Hemminki K., Peltonen K., Vodicka P. Depurination from DNA of 7-methylguanine, 7-(2-aminoethyl)-guanine and ring-opened 7-methylguanines. Chem. Biol. Interact. 70:1989;289-303.
56. Lin P.H., Nakamura J., Yamaguchi S., La D.K., Upton P.B., Swenberg J.A. Induction of direct adducts, apurinic/apyrimidinic sites and oxidized bases in nuclear DNA of human HeLa S3 tumor cells by tetrachlorohydroquinone. Carcinogenesis. 22:2001;635-639.
57. Kunkel T.A. Mutational specificity of depurination. Proc. Natl. Acad. Sci. U.S.A. 81:1984;1494-1498.
58. Shibutani S., Takeshita M., Grollman A.P. Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Nature. 349:1991;431-434.
59. Burrows C.J., Muller J.G. Oxidative nucleobase modifications leading to strand scission. Chem. Rev. 98:1998;1109-1151.
60. Kino K., Saito I., Sugiyama H. Product analysis of GG-specific photooxidation of DNA via electron transfer: 2-aminoimidazole as a major guanine oxidation product. J. Am. Chem. Soc. 120:1998;7373-7374.
61. Hirakawa K., Midorikawa K., Oikawa S., Kawanishi S. Carcinogenic semicarbazide induces sequence-specific DNA damage through the generation of reactive oxygen species and the derived organic radicals. Mutat. Res. 536:2003;91-101.
62. Kawanishi S., Yamamoto K. Mechanism of site-specific DNA damage induced by methylhydrazines in the presence of copper(II) or manganese(III). Biochemistry. 30:1991;3069-3075.