Covalent DNA adducts formed in mouse epidermis by benzo[g]chrysene

Carcinogenesis

Volumn 17, Issue 6, 1996, Pages 1331-1336

  Giles, A S ^a   Seidel, A ^b   Phillips, D H ^a  

^a INSTITUTE OF CANCER RESEARCH   (United Kingdom)

^b JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZO[G]CHRYSENE; CARCINOGEN; CHRYSENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; AUTORADIOGRAPHY; CONTROLLED STUDY; DNA ADDUCT; EPIDERMIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; MALE; METABOLIC ACTIVATION; MOUSE; NONHUMAN; PRIORITY JOURNAL; SKIN; SKIN CARCINOGENESIS; THIN LAYER CHROMATOGRAPHY; TOPICAL DRUG ADMINISTRATION;

ANIMALS; CARCINOGENS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHRYSENES; DNA; DNA ADDUCTS; MALE; MICE; MICE, INBRED STRAINS; MUTAGENS; SKIN; STEREOISOMERISM;

EID: 0029888071     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/17.6.1331     Document Type: Article

References (31)

1. Lunde, G. and Bjorseth. A. (1977) Polycyclic aromatic hydrocarbons in long-range transported aerosols. Nature (Land. ), 268, 518-519.
2. Dipple, A. , Moschel, R. C. and Bigger, C. A. H. (1984) Polynuclear aromatic carcinogens. In Searle, C. E. (ed. ), Chemical Carcinogens, 2nd Edn. American Chemical Society, Washington, DC, pp. 41-163.
3. Dipple, A. , Peltonen, K. , Cheng, S. C. and Hilton. B. D. (1993) Chemistry of DNA adduct formation by dihydrodiol epoxides of polycyclic aromatic hydrocarbons. In Garrigues, P. and Lamotte. M. (eds), Polycyclic Aromatic Hydrocarbons: Synthesis, Properties, Analytical Measurements, Occurrence and Biological Effects. Gordon and Breach Inc. , Philadelphia, PA, pp. 807-816.
4. Thakker. D. R. , Nordqvist, M. , Yagi. H. , Levin. W. , Ryan. D. , Thomas. P. E. , Conney. A. H. and Jerina, D. M. (1979) Comparative metabolism of a series of polycyclic aromatic hydrocarbons by rat liver microsomes and purified cytochrome P450. In Jones. P. W. and Leber. P. (eds), Polynuclear Aromatic Hydrocarbons: Third International Symposium on Chemistry and BiologyCarcinogenesis and Mutagenesis. Ann Arbor Science Publishers, Ann Arbor, MI, pp. 455-472.
5. Bartle. K. D. and Jones, D. W. (1972) The application of proton magnetic resonance spectroscopy to structure identification in polycyclic aromatic molecules. Adv. Org. Chem. Methods Results, 8, 317-423.
6. Dipple, A. , Pigott, M. A. , Agarwal, S. K. , Yagi. H. , Sayer, J. M. and Jerina. D. M. (1987) Optically active benzo[c]phenanthrene diol-epoxides bind extensively to adenine in DNA. Nature (Land. ), 327, 535-536.
7. Wood, A. W. , Chang. R. L. , Levin. W. , Thakker, D. R. , Yagi, H. , Sayer, J. M. , Jerina, D. M. and Conney, A. H. (1984) Mutagenicity of the enantiomers of the diastereomeric bay region benzo[c]phenanthrene-3, 4-diol-1, 2-epoxides in bacterial and mammalian cells. Cancer Res. , 44, 2320-2324.
8. McKay, J. F. and Latham, D. R. (1973) Polyaromatic hydrocarbons in highboiling petroleum distillates: isolation by gel permeation chromatography and identification by fluorescence spectrometry. Anal. Chem. , 45, 1050-1055.
9. Harris. P. N. and Bradsher. C. K. (1946) Observation on the carcinogenicity of 1, 2, 3, 4-dibenzophenanthrene and its 9-methyl and 10-methyl derivatives. Cancer Res. , 6, 671-673.
10. Hartwell, J. L. (1951) Survey of compounds which have been tested for carcinogenic activity. In US Public Health Service Publication no. 149. US Government Printing Office, Washington, DC.
11. Glatt, H. , Piée. A. , Pauly. K. , Steinbrecher, T. , Schrode. R. , Oesch. F. and Seidel, A. (1991) Fjord and bay region diol-epoxides investigated for stability, SOS induction in Escherichia coli, and mutagenicity in Salmonella typhimurium and mammalian cells. Cancer Res. , 51, 1659-1667.
12. Phillips, D. H. , Hewer, A. , Seidel. A. , Steinbrecher, T. , Schrode, R. , Oesch, F. and Glatt, H. (1991) Relationship between mutagenicity and DNA adduct formation in mammalian cells for fjord and bay region diol-epoxides of polycyclic aromatic hydrocarbons. Chem. -Biol. Interactions, 80, 177-186.
13. Amin, S. , Krzeminski, J. , Rivenson. A. , Kurtzke, C. , Hecht, S. S. and ElBayoumy. K. (1995) Mammary carcinogenicity in female CD rats of fjord region diol epoxides of benzo[c]phenanthrene, benzo[g]chrysene and dibenzo[a, l]pyrene. Carcinogenesis, 16, 1971-1974.
14. 32P-postlabeling. Chem. Res. Toxicol. , 8, 591-599.
15. Szeliga, J. , Lee. H. , Harvey. R. G. , PageJ. E. , Ross. H. L. , Routledge. M. N. , Hilton. B. D. and Dipple. A. (1994) Reaction with DNA and mutagenic specificity of syn-benzo[g]chrysene 11, 12-dihydrodiol 13, 14-epoxide. Chem. Res. Toxicol. , 7, 420-427.
16. Pruess-Schwartz, D. , Baird. W. M. , Yagi. H. , Jerina, D. M. , Pigott, M. A. and Dipple. A. (1987) Stereochemical specificity in the metabolic activation of benzo[c]phenanthrene to metabolites that covalently bind to DNA in rodent embryo cell cultures. Cancer Res. , 47, 4032-4037.
17. Thakker, D. R. , Levin. W. , Yagi. H. , Yeh, H. J. C. , Ryan. D. E. , Thomas. P. E. , Conney, A. H. and Jerina, D. M. (1986) Stereoselective metabolism of the (+)-(S, S) and (-)-(R, R)-enantiomers of trans-3, 4-dihydroxy-3, 4-dihydrobenzo[c]phenanthrene by rat and mouse liver microsomes and by a purified and reconstituted cytochrome P-450 system. J. Biol. Chem. , 261, 5404-5413.
18. Carruthers, W. (1967) Photocyclisation of some stilbene analogues. Synthesis of dibenzo[a, l]pyrene. J. Chem. Soc. , (c), 1525-1527.
19. Platt, K. L. and Oesch. F. (1983) Efficient synthesis of non-K regiondihydrodiols of polycyclic aromatic hydrocarbons from o-quinones and catechols. J. Org. Chem. , 48, 256-268.
20. Bushman, D. R. , Grossman. S. J. , Jerina, D. M. and Lehr. R. E. (1989) Synthesis of optically active fjord region 11, 12-diol 13, 14-epoxides and the K region 9, 10-oxide of the carcinogen benzo[g]chrysene. J. Org. Chem. , 54, 3533-3544.
21. Yagi, H. , Thakker, D. R. , Ittah. Y. , Croisy-Delcey. M. and Jerina. D. M. (1983) Synthesis and assignment of absolute configuration to the trans-3, 4-dihydrodiols and 3, 4-diol-l. 2-epoxides of benzo[c]phenanthrene. Tetrahedron Lett. , 24, 1349-1352.
22. Phillips, D. H. , Grover. P. L. and Sims. P. (1978) The covalent binding of polycyclic hydrocarbons to DNA in the skin of mice of different strains. Int. J. Cancer, 22, 487-494.
23. Gupta, R. C. (1984) Nonrandom binding of the carcinogen N-hydroxy-2-acetylaminofluorene to repetitive sequences of rat liver DNA in vivo. Proc. Natl Acad. Sci. USA, 81, 6943-6947.
24. 32P-postlabelling test for structurally diverse DNA adducts. Carcinogenesis, 1543-1551.
25. 32P-Postlabelling analysis of non-radioactive aromatic carcinogen-DNA adducts. Carcinogenesis, 3, 1081-1092.
26. Phillips, D. H. , Glatt, H. R. , Seidel. A. , Bochnilschek, W. , Oesch, F. and Grover, P. L. (1986) Mutagenic potential of DNA adducls formed by diol-epoxides, triol-epoxides and the K region epoxide of chrysene in mammalian cells. Carcinogenesis, 7, 1739-1743.
27. 32P-postlabelled nucleoside 3′, 5′-bisphosphate adducts of polycyclic aromatic hydrocarbons. J. Chromatogr. , 570, 65-76.
28. Levin, W. , Wood, A. W. , Chang. R. L. , Ittah. Y. , Croisy-Delcey, M. , Yagi. H. , Jerina, D. M. and Conney, A. H. (1980) Exceptionally high tumor-initiating activity of benzo[c]phenanthrene bay region diol-epoxides on mouse skin. Cancer Res. , 40, 3910-3914.
29. Ittah. Y. , Thakker, D. R. , Levin. W. , Croisy-Delcey, M. , Ryan. D. E. , Thomas, P. E. , Conney, A. H. and Jerina. D. M. (1983) Metabolism of benzo[c]phenanthrene by rat liver microsomes and by a purified monooxygenase system reconstituted with different isozymes of cytochrome P-450. Chem. -Biol. Interactions, 45, 15-28.
30. DiGiovanni, J. , Romson, J. R. , Linville, D. , Juchau, M. R. and Slaga, T. J. (1979) Covalent binding of polycyclic aromatic hydrocarbons to adenine correlates with tumorigenesis in mouse skin. Cancer Lett. , 7, 39-43.
31. DiGiovanni, J. , Sawyer, T. W. and Fisher, E. P. (1986) Correlation between formation of a specific hydrocarbon-deoxyribonucleoside adduct and tumor-initiating activity of 7, 12-dimethylbenz[a]anthracene and its 9- and 10-monofluoroderivatives in mice. Cancer Res. , 46, 4336-4341.