Interaction of benzoquinone- and hydroquinone-derivatives of lower chlorinated biphenyls with DNA and nucleotides in vitro

Chemico-Biological Interactions

Volumn 142, Issue 3, 2003, Pages 307-316

  Arif, Jamal M ^a   Lehmler, Hans Joachim ^a   Robertson, Larry W ^a   Gupta, Ramesh C ^a  

^a UNIVERSITY OF KENTUCKY MEDICAL CENTER   (United States)

Author keywords

32P postlabeling; Benzoquinone; DNA adducts; Hydroquinone; Polychlorinated biphenyl

Indexed keywords

ADENINE; BENZOQUINONE DERIVATIVE; CYTOSINE; DNA; GUANINE; HYDROQUINONE DERIVATIVE; NUCLEOTIDE; PHOSPHORUS 32; POLYCHLORINATED BIPHENYL DERIVATIVE; THYMIDINE;

ARTICLE; CHROMATOGRAPHY; COVALENT BOND; DNA ADDUCT; DNA BINDING; NONHUMAN;

BENZOQUINONES; DNA; DNA ADDUCTS; DNA DAMAGE; HYDROQUINONES; NUCLEOTIDES; POLYCHLORINATED BIPHENYLS;

RODENTIA;

EID: 0037420968     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(02)00141-2     Document Type: Article

References (39)

1. Risebrough R.W., Rieche P., Herman S.G., Peakall D.B., Kirven M.N. Polychlorinated biphenyls in the global ecosystem. Nature. 220:1968;1098-1102.
2. Safe S. Polychlorinated biphenyls (PCBs): environmental impact, biochemical and toxic responses and implications for risk assessment. CRC Crit. Rev. Toxicol. 24:1994;87-149.
3. Hansen L.G. The Ortho Side of PCBs: Occurrence and Disposition. 1999;KluverAcademicPublisher, Massachusetts, USA.
4. Loomis D., Browning S.R., Schenck A.P., Gregory E., Savitz D.A. Cancer mortality among electric utility workers exposed to polychlorinated biphenyls. Occup. Environ. Med. 54:1997;720-728.
5. Robertson L.W., Hansen L.G. PCBs:Recent Advances in the Environmental Toxicology and Health Effects. 2001;The University Press of Kentucky, Lexington, Kentucky, USA.
6. Wolff M.S., Weston A. Breast cancer risk and environmental exposures. Environ. Health Perspect. 105:1997;891-896.
7. Krieger N., Wolff M.S., Hiatt R.A., Rivera M., Vogelman J., Orentreich N. Breast cancer and serum organochlorines: a prospective study among white, black, and Asian women. J. Natl. Cancer Inst. 86:1994;589-599.
8. Safe S., Safe L., Mullin M. Polychlorinated biphenyls (PCBs)-congener-specific analysis of a commercial mixture and human milk extract. J. Agric. Food Chem. 33:1985;24-28.
9. Quinsey P.M., Donohue D.C., Ahokas J.T. Persistence of organochlorines in breast milk of women in Victoria, Australia. Food Chem. Toxicol. 33:1995;49-56.
10. Demers A., Ayotte P., Brisson J., Dodin S., Robert J., Dewailly E. Plasma concentrations of polychlorinated biphenyls and the risk of breast cancer: a congener-specific analysis. Am. J. Epidemiol. 155:2002;629-635.
11. Lucena R.A., Allam M.F., Costabeber I.H., Villarejo M.L., Navajas R.F. Breast cancer risk factors: PCB congeners. Eur. J. Cancer Prev. 10:2001;117-119.
12. Zheng T., Holford T.R., Tessari J., Mayne S.T., Owens P.H., Ward B., Carter D., Boyle P., Dubrow R., Archibeque-Engle S. Breast cancer risk associated with congeners of polychlorinated biphenyls. Am. J. Epidemiol. 152:2000;50-58.
13. Mayes B.A., McConnell E.E., Neal B.N., Brunner M.J., Hamilton S.B., Sullivan T.M., Peter A.C., Ryan M.J., Toft J.D., Singer A.W., Brown J.F., Menton R.G., Moore J.A. Comparative carcinogenicity in Sprague-Dawley rats of the polychlorinated biphenyl mixtures Aroclor 1016, 1242, 1254, and 1260. Toxicol. Sci. 41:1998;62-76.
14. Pereg D., Tampal N., Espandiari P., Robertson L.W. Distribution and macromolecular binding of benzo[a]pyrene and two polychlorinated biphenyl congeners in female mice. Chem. Biol. Interact. 137:2001;243-258.
15. Narbonne J.F., Daubeze M. In vitro binding of hexachlorobiphenyl to DNA and proteins. Toxicology. 16:1980;173-175.
16. Sundstorm G., Hutzinger O., Safe S. The metabolism of chlorobiphenyls - a review. Chemosphere. 5:1976;267-298.
17. Oakley G.G., Devanaboyina U.S., Robertson L.W., Gupta R.C. Oxidative DNA damage induced by activation of polychlorinated biphenyls (PCBs): implications for PCB-induced oxidative stress in breast cancer. Toxicol. Chem. Res. 9:1996;1285-1292.
18. McLean M.R., Bauer U., Amaro A.R., Robertson L.W. Identification of catechol and hydroquinone metabolites of 4-monochlorobiphenyl. Chem. Res. Toxicol. 9:1996;159-164.
19. Pereg D., Robertson L.W., Gupta R.C. DNA adduction by polychlorinated biphenyls: adducts derived from hepatic microsomal activation and from synthetic metabolites. Chem. Biol. Interact. 139:2002;129-144.
20. Nath R.G., Randerath E., Randerath K. Short-term effects of tumor promoting polychlorobiphenyl mixture, Aroclor 1254, on I-compounds in liver, kidney and lung DNA of male Sprague-Dawley rats. Toxicology. 68:1991;275-289.
21. 32P-postlabeling assay. Toxicol. Appl. Pharmacol. 148:1998;14-23.
22. Schilderman P.A.E.L., Maas L.M., Pachen D.M.F.A., de Kok T.M.C.M., Kleinjans J.C.S., van Schooten F.J. Induction of DNA adducts by several polychlorinated biphenyls. Environ. Mol. Mutag. 36:2000;79-86.
23. Butterworth F.M., Pandey P., McGowen R.M., Ali-Sadat S., Walia S. Genotoxicity of polychlorobiphenyls (PCBs): recombinogenesis by biotransformation products. Mut. Res. 342:1995;61-69.
24. 32P-postlabeling for detection of DNA adducts. Pfeifer G.P., Technologies for Detection of DNA Damage and Mutations. 1996;45-61 Plenum Press, New York.
25. Brassard P., L'Écuyer P. L'Arylation des quinones par les sels de diazonium. Can. J. Chem. 36:1958;700-708.
26. Brassard P., L'Écuyer P. L'Arylation des quinones par les sels de diazonium. III. Sur la synthese des aryl-chloro-p-benzoquinones. Can. J. Chem. 36:1958;814-819.
27. Bauer U., Amaro A.R., Robertson L.W. A new strategy for the synthesis of polychlorinated biphenyl metabolites. Chem. Res. Toxicol. 8:1995;92-95.
28. Amaro A.R., Oakley G.G., Bauer U., Spielmann H.P., Robertson L.W. Metabolic activation of PCBs to quinones: reactivity toward nitrogen and sulfur nucleophiles and influence of superoxide dismutase. Chem. Res. Toxicol. 9:1996;623-629.
29. Arif J.M., Shappel N., Sikka H., Kumar S., Gupta R.C. Identification of (±)-3-hydroxy-trans-7,8-dihydroxy-9,10-epoxy-7,8,9,10- etrahydrobenzo[a]pyrene-DNA adducts by 32P-postlabeling. Chem. Bio. Interac. 118:1999;87-97.
30. 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis. 7:1986;1543-1551.
31. 32P-postlabeling assay for the sensitive detection of 8-oxodeoxyguanosine in tissue DNA. Chem. Res. Toxicol. 14:2001;951-957.
32. Abul-Hajj Y.J., Tabakovic K., Tabakovic I. An estrogen-nucleic acid adduct. Electroreductive intermolecular coupling of 3,4-estrone-o-quinone and adenine. J. Am. Chem. Soc. 117:1995;6144-6145.
33. Akanni A., Tabakovic K., Abul-Hajj Y.J. Estrogen-nucleic acid adducts: reaction of 3,4-estrone o-quinone with nucleic acid bases. Chem. Res. Toxicol. 10:1997;477-481.
34. Akanni A., Abul-Hajj Y.J. Estrogen-nucleic acid adducts: reaction of 3,4-estrone-o-quinone radical anion ithdeoxyribonucleosides. Chem. Res. Toxicol. 10:1997;760-766.
35. Shen L., Qui S., van Breemen R.B., Zhang F., Chen Y., Bolton J.L. Reaction of the Premarin metabolite 4-hydroxyequilenin semiquinone radical with 2′-deoxyguanosine: formation of unusual cyclic adducts. J. Am. Chem. Soc. 119:1997;11126-11127.
36. Shen L., Qiu S., Chen Y., Zhang F., van Breemen R.B., Nikolic D., Bolton J.L. Alkylation of 2′-deoxynucleosides and DNA by the Premarin metabolite 4-hydroxyequilenin semiquinone radical. Chem. Res. Toxicol. 11:1998;94-101.
37. Musso H., Döpp H. Autoxydationsgeschwindigkeit and redoxpotential by hydrochinon-, brenzcatechin- und resorcinderivaten. Chem. Ber. 100:1967;3627-3643.
38. Chenna A., Singer B. Large scale synthesis of p-benzoquinone-2'-deoxycytidine and p-benzoquinone-2′-deoxyadenosine adducts and their site-specific incorporation into DNA oligonucleotides. Chem. Res. Toxicol. 8:1995;865-874.
39. Jowa L., Witz G., Snyder R., Winkle S., Kalf G.F. Synthesis and characterization of deoxyguanosine-benzoquinone adducts. J. Appl. Toxicol. 10:1990;47-54.