Oxidative dna damage induced by activation of polychlorinated biphenyls (pcbs): Implications for pcb-induced oxidative stress in breast cancer

Chemical Research in Toxicology

Volumn 9, Issue 8, 1996, Pages 1285-1292

  Oakley, Gregory G ^b   Devanaboyina, Diapason ^b   Robertson, Larry W ^b   Gupta, Ramesh C ^a,b  

^a UNIVERSITY OF KENTUCKY MEDICAL CENTER   (United States)

^b UNIVERSITY OF KENTUCKY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8 HYDROXYDEOXYGUANOSINE; CATALASE; COPPER CHLORIDE; DEOXYGUANOSINE; FERROUS CHLORIDE; GLUTATHIONE; HYDROGEN PEROXIDE; LACTOPEROXIDASE; POLYCHLORINATED BIPHENYL DERIVATIVE; SODIUM AZIDE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG;

ARTICLE; BREAST CANCER; CONTROLLED STUDY; DNA DAMAGE; HUMAN; HUMAN TISSUE; OXIDATION; OXIDATIVE STRESS; ULTRAVIOLET SPECTROSCOPY;

ANIMALS; BIOTRANSFORMATION; BREAST NEOPLASMS; CARCINOGENS; CATTLE; COPPER; DNA DAMAGE; FERRIC COMPOUNDS; FREE RADICAL SCAVENGERS; HUMANS; HYDROGEN PEROXIDE; LACTOPEROXIDASE; OXIDATION-REDUCTION; OXIDATIVE STRESS; POLYCHLORINATED BIPHENYLS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0029803656     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx960103o     Document Type: Article

References (60)

1. Erickson, M. D. (1986) Analytical Chemistry of PCBs, Butterworth Publishers, Boston.
2. Silberhorn, E. M., Glauert, H. P., and Robertson, L. W. (1990) Carcinogenicity of Polyhalogenated Biphenyls: PCBs and PBBs. CRC Crit. Rev. Toxicol. 20, 439-496.
3. Wolff, M. S., Toniolo, P. G., Lee, E. W., Rivera, M., and Dubin, N. (1993) Blood levels of organochlorine residues and risk of breast cancer. J. Natl. Cancer Inst. 85, 648-652.
4. Krieger, N., Wolff, M. S., Hiatt, R. A., Rivera, M., Vogelman, J., and Orentreich, N. (1994) Breast cancer and serum organchlorines: a prospective study among white, black, and asian women. J. Natl. Cancer Inst. 86, 589-599.
5. Wassermann, M., Nogueira, D. P., Tomatis, L., Mirra, A. P., Shibata, H., Arie, G., Cucos, S., and Wassermann, D. (1976) Organochlorine compounds in neoplastic and adjacent apparently normal breast tissue. Bull. Environ. Contam. Toxicol. 15, 478-484.
6. Falck, F., Ricci, A., Wolff, M. S., Godbold, J., and Deckers, P. (1992) Pesticides and polychlorinated biphenyl residues in human breast lipids and their relation to breast cancer. Arch. Environ. Health 47, 143-146.
7. Safe, S., Safe, L., and Mullin, M. (1985) Polychlorinated biphenyls (PCBs)-congener-specific analysis of a commercial mixture and a human milk extract. J. Agric. Food Chem. 33, 24-28.
8. Johansen, H. R., Becher, G., Polder, A., and Skaare, J. U. (1994) Congener-specific determination of polychlorinated biphenyls and organochlorine pesticides in human milk from Norwegian mothers living in Oslo. J. Toxicol. Environ. Health 42, 157-171.
9. Quinsey, P. M., Donohue, D. C., and Ahokas, J. T. (1995) Persistence of organochlorines in breast milk of women in Victoria, Australia. Food Chem. Toxicol. 33, 49-56.
10. Amaro, A., Oakley, G. G., Bauer, U., Spielmann, H. P., and Robertson, L. W. (1996) Metabolic activation of PCBs to quinones: reactivity toward nitrogen and sulfur nucleophiles and influence of Superoxide dismutase. Chem. Res. Toxicol. 9, 623-629.
11. Liehr, J. G., and Roy, D. (1990) Free radical generation by redox cycling of estrogens. Free Radical Biol. Med. 8, 415-423.
12. Nutter, L. M., Ngo, E. O., and Abul-Hajj, Y. S. (1991) Characterization of DNA damage induced by 3,4-estrone-o-quinone in human cells. J. Biol. Chem. 266, 16380-16386.
13. Han, X., and Liehr, J. G. (1994) DNA single strand breaks in kidneys of Syrian hamsters treated with steroidal estrogens: hormone-induced free radical damage preceding renal malignancy. Carcinogenesis 15, 997-1000.
14. Nutter, L. M., Wu, Y. Y., Ngo, E. O., Sierra, E. E., Gutierrez, P. L., and Abul-Hajj, Y. S. (1994) An o-quinone form of estrogen produces free radicals in human breast cancer cells: correlation with DNA damage. Chem. Res. Toxicol. 7, 23-28.
15. Han, X., and Liehr, J. G. (1995) Microsome-mediated 8-hydroxylation of guanine bases of DNA by steroid estrogens: correlation of DNA damage by free radicals with metabolic activation to quinones. Carcinogenesis 16, 2571-2574.
16. Han, X., and Liehr, J. G. (1994) 8-Hydroxylation of guanine bases in kidney and liver DNA of hamsters treated with estradiol: role of free radicals in estrogen-induced Carcinogenesis. Cancer Res. 54, 5515-5517.
17. Bergman, A., Klasson-Wehler, E., and Kuroki, H. (1994) Selective retention of hydroxylated PCB metabolites in blood. Environ. Health Perspect. 102, 464-469.
18. 32P-postlabeling. Carcinogenesis 17, 109-114.
19. Li, Y., and Trush, M. A. (1993) Oxidation of hydroquinone by copper: chemical mechanism and biological effects. Arch. Biochem. Biophys. 300, 346-355.
20. Li, Y., Trush, M. A., and Yager, J. D. (1994) DNA damage caused by reactive oxygen species originating from a copper-dependent oxidation of the 2-hydroxy catechol of estradiol. Carcinogenesis 15, 1421-1427.
21. Malins, D. C., Polissar, N. L., and Gunselman, S. J. (1996) Progression of human breast cancers to the metastatic state is linked to hydroxyl radical-induced DNA damage. Proc. Natl. Acad. Sci. U.S.A. 93, 2557-2563.
22. 32P-Postlabeling analysis of bulky aromatic adducts. In Postlabeling Methods for Detection of DNA Adducts (Phillips, D. H., Castegnaro, M., and Bartsch, H., Eds.) pp 11-23, IARC, Lyon.
23. 32P]cGMP, and their use in assay of adenylate and guanylate cyclases, and cyclic nucleotide phosphodiesterases. Adv. Cyclic Nucleotide Res. 10, 135-167.
24. 32P-Postlabeling Analysis of Aromatic Carcinogen:DNA Adducts. Cancer Res. 45, 5656-5662.
25. 32P-postlabeling assay and the basal levels in rat tissues. Carcinogenesis 17, 917-924.
26. Bauer, U., Amaro, A., and Robertson, L. W. (1995) A new strategy for the synthesis of polychlorinated biphenyl metabolites. Chem. Res. Toxicol. 8, 92-95.
27. Brassard, P., and L'Ecuyer, P. (1958) L'Arylation des quinones par les sels de diazonium (The arylation of quinones by diazonium salts). Can. J. Chem. 36, 700-708.
28. 32P-postlabeling technique. Chem. Res. Toxicol. 9, 165-171.
29. Ludewig, G., Oakley, G., Espandiari, P., and Robertson, L. W. (1996) Production of Superoxide and DNA strand breaks by diol metabolites of lower chlorinated biphenyls (PCBs). Proc. Am. Assoc. Cancer Res. 37, Abstract 989.
30. Meister, A. (1988) Glutathione metabolism and its selective modification. J. Biol. Chem. 263, 17205-17208.
31. Winterbourn, C. C. (1993) Superoxide as an intracellular radical sink. Free Radical Biol. Med. 14, 85-90.
32. Reed, C. J., and Douglas, K. T. (1991) Chemical cleavage of plasmid DNA by glutathione in the presence of Cu(II) ions. Biochem. J. 275, 601-608.
33. Li, Y., and Trush, M. A. (1993) DNA damage resulting from the oxidation of hydroquinone by copper: role for a Cu(II)/Cu(I) redox cycle and reactive oxygen generation. Carcinogenesis 14, 1303-1311.
34. Tsou, T. C., Chen, C. L., Liu, T. Y., and Yang, J. L. (1996) Induction of 8-oxodeoxyguanosine in DNA by chromium(III) plus hydrogen peroxide and its prevention by scavengers. Carcinogenesis 17, 103-108.
35. Eichhorn, G. L., Clark, P., and Becker, E. D. (1966) Interactions of metal ions with polynucleotides and related components. VII. The binding of copper(II) to nucleosides, nucleotides and deoxyribonucleic acids. Biochemistry 5, 245-253.
36. Rao, D. N. R., Glitter, W. D., and Mason, R. P. (1988) The formation of free radical metabolites by mammalian peroxidases. In Cellular antioxidant defense mechanisms (Chow, C. K., Ed.) pp 59-71, CRC Press, Boca Raton, FL.
37. Agarwal, K., Sharma, A., and Talukder, G. (1989) Effects of copper on mammalian cell components. Chem.-Biol. Interact. 69, 1-16.
38. Geierstanger, B. H., Kagawa, T. F., Chen, S. L., Quigley, G. J., and Ho, P. S. (1991) Base-specific binding of copper(II) to Z-DNA. J. Biol. Chem. 266, 20185-20191.
39. Kagawa, T. F., Geierstanger, B. H., Wang, A. H. J., and Ho, P. S. (1991) Covalent modification of guanine bases in double-stranded DNA. J. Biol. Chem. 266, 20175-20184.
40. Kuchino, Y., Mori, F., Kasai, H., Inoue, H., Iwai, S., Miura, K., Ohtsuka, E., and Nixhimura, S. (1987) Misreading of DNA templates containing 8-oxodeoxyguanosine at the modified base and at adjacent residues. Nature 327, 77-79.
41. Nagai, F., Ushiyama, K., Satoh, K., Kasai, H., and Kano, I. (1995) Formation of 8-oxodeoxyguanosine in calf thymus DNA treated in vitro with phenylhydroquinone, the major metabolite of O-phenylphenol. Carcinogenesis 16, 837-840.
42. Nagai, F., Ushiyama, K., Satoh, K., and Kano, I. (1990) DNA cleavage by phenylhydroquinone: the major metabolite of a fungicide o-phenylphenol. Chem.-Biol. Interactions 76, 163-179.
43. Inoue, S., Yamamoto, K., and Kawanishi, S. (1990) DNA damage induced by metabolites of o-phenylphenol in the presence of copper(II) ion. Chem. Res. Toxicol. 3, 144-149.
44. Yamamoto, K., and Kawanishi, S. (1989) 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.
45. Yamamoto, K., and Kawanishi, S. (1991) Site-specific DNA damage induced by hydrazine in the presence of manganese and copper ions. J. Biol. Chem. 266, 1509-1515.
46. Zhang, L., Bandy, B., and Davison, A. J. (1996) Effects of metals, ligands and antioxidants on the reaction of oxygen with 1,2,4-benzenetriol. Free Radical Biol. Med. 20, 495-505.
47. Yamamoto, K., Inoue, S., Yamazaki, A., Yoshinaga, T., and Kawanishi, S. (1989) Site-specific DNA damage induced by cobalt(II) ion and hydrogen peroxide: role of singlet oxygen. Chem. Res. Toxicol. 2, 234-239.
48. Seacat, A. M., Groopman, J. D., and Yager, J. D. (1996) DNA damage resulting from the oxidation of catechol estrogens by copper: comparison of 8-oxodeoxyguanosine (8-OXO-dG) to DNA strand break formation. Fundam. Appl. Toxicol. 30, 68#354.
49. Li, Y., and Trush, M. A. (1994) Reactive oxygen-dependent DNA damage resulting from the oxidation of phenolic compounds by a copper-redox cycle mechanism. Cancer Res. 54, 1895s-1898s.
50. Reed, C. J., and Douglas, K. T. (1989) Single-strand cleavage of DNA by Cu(II) and thiols: a powerful chemical DNA-cleaved system. Biochem. Biophys. Res. Commun. 162, 1111-1117.
51. Milne, L., Nicotera, P., Orrenius, S., and Burkitt, M. J. (1993) Effects of glutathione and chelating agents on copper-mediated DNA oxidation: Pro-oxidant and antioxidant properties of glutathione. Arch. Biochem. Biophys. 304, 102-109.
52. Hollenberg, P. F. (1992) Mechanisms of cytochrome P450 and peroxidase-catalyzed xenobiotic metabolism. FASEB J. 6, 689-694.
53. Sawada, Y., Iyanagi, T., and Yamazaki, I. (1975) Relation between Redox Potentials and Rate Constants in Reactions Coupled with the System Oxygen-Superoxide. Biochemistry 14, 3761-3764.
54. Schreiber, J., Foureman, G. L., Hughes, M. F., Mason, R. P., and Eling, T. E. (1989) Detection of glutathione thiyl free radical catalyzed by prostaglandin H synthase present in keratinocytes. J. Biol. Chem. 264, 7936-7943.
55. Ross, D., Mehlhorn, R. J., Moldeus, P., and Smith, M. T. (1985) Metabolism of diethylstilbestrol by horseradish peroxidase and prostaglandin-H synthase. J. Biol. Chem. 260, 16210-16214.
56. Pichorner, H., Metodiewa, D., and Winterbourn, C. C. (1995) Generation of Superoxide and tyrosine peroxide as a result of tyrosyl radical scavenging by glutathione. Arch. Biochem. Biophys. 323, 429-437.
57. Sipe, H. J., Jr., Jordan, S. J., Hanna, P. M., and Mason, R. P. (1994) The metabolism of 17B-estradiol by lactoperoxidase: a possible source of oxidative stress in breast cancer. Carcinogenesis 15, 2637-2643.
58. Stoyanovsky, D. A., Goldman, R., Claycamp, H. G., and Kagan, V. E. (1995) Phenoxyl radical-induced thiol-dependent generation of reactive oxygen species: Implications for benzene toxicity. Arch. Biochem. Biophys. 317, 315-323.
59. Monks, T. J., and Lau, S. S. (1992) Toxicology of quinonethioethers. CRC Crit. Rev. Toxicol. 22, 243-270.
60. Le Page, F., Margot, A., Grollman, A. P., Sarasin, A., and Gentil, A. (1995) Mutagenicity of a unique 8-oxoguanine in a human Haras sequence in mammalian cells. Carcinogenesis 16, 2779-2784.