Benzo[c]phenanthrene 3,4-dihydrodiol 1,2-epoxide adducts in native and denatured DNA

Carcinogenesis

Volumn 17, Issue 8, 1996, Pages 1773-1776

  Agarwal, Rajiv ^a   Yagi, Haruhiko ^b   Jerina, Donald M ^b   Dipple, Anthony ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE; BENZO[C]PHENANTHRIDINE DERIVATIVE; DEOXYADENOSINE; EPOXIDE; HYDROCARBON;

ARTICLE; CONTROLLED STUDY; DNA ADDUCT; DNA DENATURATION; DNA STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; PRIORITY JOURNAL; ULTRAVIOLET SPECTROSCOPY;

EID: 0029784573     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/17.8.1773     Document Type: Article

References (25)

1. Levin, W., Wood, A.W., Yagi, H., Jerina, D.M. and Conney, A.H. (1976) (±)-Trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene: a potent skin carcinogen when applied topically to mice. Proc. Natl Acad. Sci. USA, 73, 3867-3871.
2. Amin, S., Desai, D. and Hecht, S.S. (1993) Tumor-initiating activity on mouse skin of bay region diol-epoxides of 5,6-dimethylchrysene and benzo[c]phenanthrene. Carcinogenesis, 14, 2033-2037.
3. Levin, W., Chang, R.L., Wood, A., Thakker, D.R., Yagi, H., Jerina, D.M. and Conney, A.H. (1986) Tumorigenicity of optical isomers of the diastereomeric bay region 3,4-diol 1,2-epoxides of benzo[c]phenanthrene in murine tumor models. Cancer Res., 46, 2257-2261.
4. Dipple, A., Moschel, R.C. and Bigger C.A.H. (1984) Polynuclear aromatic carcinogens. In Searle, C.E. (ed.), Chemical Carcinogens. American Chemical Society, Washington, DC. pp. 41-163.
5. Harvey, R.G. (1991) Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity. Cambridge University Press, Cambridge, UK.
6. Jerina, D.M., Chadha, A., Cheh, A.M., Schurdak, M.E., Wood, A.W. and Sayer, J.M. (1991) Covalent bonding of bay-region diol epoxides to nucleic acids. In Witmer, C.M., Snyder, R., Jollow, D.J., Kalf, G.F., Kocsis, J.J. and Sipes, I.G. (eds), Biological Reactive Intermediates IV. Molecular and Cellular Effects and Their Impact on Human Health, Advances in Experimental Medicine and Biology, Vol. 283. Plenum Press, New York, NY, pp. 533-553.
7. Sayer, J.M., Yagi, H., Croisy-Delcey, M. and Jerina, D.M. (1981) Novel bay-region diol epoxides from benzo[c]phenanthrene. J. Am. Chem. Soc., 103, 4970-4972.
8. 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-1,2-epoxides of benzo[c]phenanthrene. Tetrahedron Lett., 24, 1349-1352.
9. Jerina, D.M., Sayer, J.M., Agarwal, S.K. et al. (1986) Reactivity and tumorigenicity of bay-region diol epoxides derived from polycyclic aromatic hydrocarbons. In Kocsis, J.J., Jollow, D.J., Witmer, C.M., Nelson, J.O. and Snyder, R. (eds), Biological Reactive Intermediates III. Plenum Press, New York, NY, pp. 11-30.
10. 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 embyro cell cultures. Cancer Res., 47, 4032-4037.
11. Dipple, A., Pigott, M.A., Agarawal, 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, 327, 535-536.
12. Agarwal, S.K., Sayer, J.M., Yeh, H.J.C., Pannell, L.K., Hilton, B.D., Pigott, M.A., Dipple, A., Yagi, H. and Jerina, D.M. (1987) Chemical characterization of DNA adducts derived from the configurationally isomeric benzo-[c]phenanthrene-3,4-diol 1,2-epoxides. J. Am. Chem. Soc., 109, 2497-2504.
13. 32P-postlabeling assay. Chem. Res. Toxicol., 5, 685-690.
14. Cheh, A.M., Yagi, H. and Jerina, D.M. (1990) Stereoselective release of polycyclic aromatic hydrocarbon deoxyadenosine adducts from DNA by the phosphorus-32 postlabeling and DNAse I snake venom phosphodiesterase digestion methods. Chem. Res. Toxicol., 3, 545-550.
15. Cheh, A.M., Yagi, H. and Jerina, D.M. (1994) Effect of DNA base sequence on the configuration of deoxyadenosine adducts formed by the fjord region diol epoxide, (+)-(1R,2S,3R,4S)-3,4-dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrobenzo[c] phenanthrene. Biochemistry, 33, 12911-12919.
16. Dipple, A. and Pigott, M.A. (1987) Resistance of 7,12-dimethyl-benz[a]anthracene deoxyadenosine adducts in DNA to hydrolysis by snake venom phosphodiesterase. Carcinogenesis, 8, 491-493.
17. Sawicki, J.T., Moschel, R.C. and Dipple, A. (1983) Involvement of both syn-and anti-dihydrodiol epoxides in the binding of 7,12-dimethyl-benz[a]anthracene to DNA in mouse embryo cell cultures. Cancer Res., 43, 3212-3218.
18. 32P-Postlabeling analysis of non-radioactive aromatic carcinogen-DNA adducts. Carcinogenesis, 3, 1081-1092.
19. 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis, 7, 1543-1551.
20. 32P-postlabeling. Chem. Res. Toxicol., 8, 591-599.
21. SAS Institute Inc. (1985) SAS Users Guide: Statistics, Version 5. SAS Institute Inc., Cary, NC, pp. 795-800.
22. Jerina, D.M. et al. (1984) Identification of the ultimate carcinogenic metabolites of the polycyclic aromatic hydrocarbons: bay-region (R,S)-diol-(S,R)-epoxides. In Caldwell, J. and Paulson, G.D. (eds), Foreign Compound Metabolism. Taylor and Francis, London, UK, pp. 257-266.
23. Cosman, M., Fiala, R., Hingerty, B.E. et al. (1993) Solution conformation of the (+)-trans-anti-[BPh]dA adduct opposite dT in a DNA duplex: intercalation of the covalently attached benzo[c]phenanthrene to the 5′-side of the adduct site without disruption of the modified base pair. Biochemistry, 32, 12488-12497.
24. Cosman, M., Laryea, A., Fiala, R., Hingerty, B.E., Amin, S., Geacintov, N.E., Broyde, S. and Patel, D.J. (1995) Solution conformation of the (-)-trans-anti-benzo[c]phenanthrene-dA ([BPh]dA) adduct opposite dT in a DNA duplex: intercalation of the covalently attached benzo[c]phenanthrene ring to the 3′-side of the adduct site and comparison with the (+)-trans-anti-[BPh]dA opposite dT stereoisomer. Biochemistry, 34, 1295-1307.
25. Sayer, J.M., Chadha, A., Agarwal, S.K., Yeh, H.J.C., Yagi, H. and Jerina, D.M. (1991) Covalent nucleoside adducts of benzo[a]pyrene 7,8-diol 9,10-epoxides: structural reinvestigation and characterization of a novel adenosine adduct on the ribose moiety. J. Org. Chem., 56, 20-29.