31
Views
8
CrossRef citations to date
0
Altmetric
Original Article

Sequence-specific DNA damage induced by carcinogenic danthron and anthraquinone in the presence of Cu(II), cytochrome P450 reductase and NADPH

, &
Pages 595-604 | Received 12 Sep 2000, Published online: 07 Jul 2009

References

  • IARC Working Group on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Dantron. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. IARC, Lyon 1990; 50: 265–275, In
  • Mori H., Sugie S., Niwa K., Yoshimi N., Tanaka T., Hirono I. Carcinogenicity of chrysazin in large intestine and liver of mice. Japanese Journal of Cancer Research 1986; 77: 871–876
  • Mori H., Sugie S., Niwa K., Takahashi M., Kawai K. Introduction of intestinal tumors in rats by chrysazin. British Journal of Cancer 1985; 52: 781–783
  • NTP Working Group. TR-494 Toxicology and Carcinogenesis Studies of Anthraquinone (CAS No. 84-65-1) in F344/N Rats and B6C3F1 Mice (Feed Studies). NTP Board of Scientific Counselor's Technical Reports. 1999, In
  • Mueller S.O., Stopper H. Characterization of the genotoxicity of anthraquinones in mammalian cells. Biochimica et Biophysica Acta 1999; 1428: 406–414
  • Chesis P.L., Levin D.E., Smith M.T., Ernster L., Ames B.N. Mutagenicity of quinones: Pathways of metabolic activation and setoxification. Proceedings of National Academy of Science 1984; 81: 1696–1700
  • O'Brien P.J. Molecular mechanisms of quinone cytotoxicity. Chemico-Biological Interactions 1992; 80: 1–41
  • Monks T.J., Hanzlik R.P., Cohen G.M., Ross D., Graham D.G. Contemporary issues in toxicology. Quinone chemistry and toxicity. Toxicology and Applied Pharmacology 1992; 112: 2–16
  • Akman S.A., Doroshow J.H., Burke T.G., Dizdaroglu M. DNA base modifications induced in isolated human chromatin by NADH dehydrogenase-catalyzed reduction of doxorubicin. Biochemistry 1992; 31: 3500–3506
  • Cadenas E. Antioxidant and prooxidant functions of DT-diaphorase in quinone metabolism. Biochemical Pharmacology 1995; 49: 127–140
  • Hiraku Y., Kawanishi S. Oxidative DNA damage and apoptosis induced by benzene metabolites. Cancer Research 1996; 56: 5172–5178
  • Murata M., Moriya K., Inoue S., Kawanishi S. Oxidative damage to cellular and isolated DNA by metabolites of a fungicide ortho-phenylphenol. Carcinogenesis 1999; 20: 851–857
  • Bolton J.L., Trush M.A., Panning T.M., Dryhurst G., Monks T.J. Role of quinones in toxicology. Chemical Research in Toxicology 2000; 13: 135–160
  • Chumakov P. EMBL Data Library. 1990, Accession Number X54156
  • 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 1983; 302: 33–37
  • 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). Mutation Research 1998; 397: 191–201
  • 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. Journal of Biological Chemistry 1991; 266: 1509–1515
  • Kawanishi S., Yamamoto K. Mechanism of site-specific DNA damage induced by methylhydrazines in the presence of copper(II) or manganese(III). Biochemistry 1991; 30: 3069–3075
  • Maxam A.M., Gilbert W. Sequencing end-labeled DNA with base-specific chemical cleavages. Methods in Enzymology 1980; 65: 499–560
  • 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 1986; 7: 1849–1851
  • Ito K., Inoue S., Yamamoto K., Kawanishi S. 8-Hydroxy-deoxyguanosine formation at the 5′ site of 5′-GG-3′ sequences in double-stranded DNA by UV radiation with riboflavin. Journal of Biological Chemistry 1993; 268: 13221–13227
  • Kawanishi S., Inoue S., Sano S. Mechanism of DNA cleavage induced by sodium chromate (VI) in the presence of hydrogen peroxide. Journal of Biological Chemistry 1986; 261: 5952–5958
  • Pryor W.A., Tang R.H. Ethylene formation from methional. Biochemical and Biophysical Research Communications 1978; 81: 498–503
  • Rao P.S., Luber J.M., Jr., Milinowicz J., Lalezari P., Mueller H.S. Specificity of oxygen radical scavengers and assessment of free radical scavenger efficiency using luminol enhanced chemiluminescence. Biochemical and Biophysical Research Communications 1988; 150: 39–44
  • Denissenko M.F., Pao A., Tang M., Pfeifer G.P. Preferential formation of benzo[a]pyrene adducts at lung cancer mutational hotspots in p53. Science 1996; 274: 430–432
  • Hollstein M., Sidransky D., Vogelstein B., Harris C.C. p53 Mutations in human cancers. Science 1991; 253: 49–53
  • Sugiyama H., Saito I. Theoretical studies of GG-specific photocleavage of DNA via electron transfer: significant lowering of ionization potential and 5′-localization of HOMO of stacked GG bases in B-form DNA. Journal of the American Chemical Society 1996; 118: 7063–7068
  • Celander D.W., Cech T.R. Iron(II)-ethylene-diaminetetraacetic acid catalyzed cleavage of RNA and DNA oligonucleotides: Similar reactivity toward single- and double-stranded forms. Biochemistry 1990; 29: 1355–1361
  • Rodriguez H., Drouin R., Holmquist G.P., O'Connor T.R., Boiteux S., Laval J., Doroshow J.H., Akman S.A. Mapping of copper/hydrogen peroxide-induced DNA damage at nucleotide resolution in human genomic DNA by ligation-mediated polymerase chain reaction. Journal of Biological Chemistry 1995; 270: 17633–17640
  • Yamamoto K., Kawanishi S. Hydroxyl free radical is not the main active species in site-specific DNA damage induced by copper(II) ion and hydrogen peroxide. Journal of Biological Chemistry 1989; 264: 15435–15440
  • Oikawa S., Kawanishi S. Distinct mechanisms of site-specific DNA damage induced by endogenous reductants in the presence of iron(II) and copper(II). Biochimica et Biophysica Acta 1998; 1399: 19–30
  • Burkitt M.J. Copper-DNA adducts. Methods in Enzymology 1994; 234: 66–79
  • Dizdaroglu M. Oxidative damage to DNA in mammalian chromatin. Mutation Research 1992; 275: 331–342
  • Burrows C.J., Muller J.G. Oxidative nucleobase modifications leading to strand scission. Chemical Reviews 1998; 98: 1109–1151
  • Kino K., Saito I., Sugiyama H. Product analysis of GG-specific photooxidation of DNA via electron transfer: 2-aminoimidazolone as a major guanine oxidation product. Journal of the American Chemical Society 1998; 120: 7373–7374
  • Shibutani S., Takeshita M., Grollman A.P. Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Nature 1991; 349: 431–434
  • Duarte V., Muller J.G., Burrows C.J. Insertion of dGMP and dAMP during in vitro DNA synthesis opposite an oxidized form of 7,8-dihydro-8-oxoguanine. Nucleic Acids Research 1999; 27: 496–502

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.