Benzo[c]phenanthrene - DNA adducts in mouse epidermis in relation to the tumorigenicities of four configurationally isomeric 3,4-dihydrodiol 1,2-epoxides

Chemical Research in Toxicology

Volumn 9, Issue 3, 1996, Pages 586-592

  Agarwal, Rajiv ^a   Canella, Karen A ^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

1,2 EPOXY 3,4 DIHYDROBENZO[C]PHENANTHRENE 3,4 DIOL; BENZO[C]PHENANTHRENE; EPOXIDE; PHENANTHRENE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL MODEL; ARTICLE; CARCINOGENICITY; CONTROLLED STUDY; DNA ADDUCT; DNA MODIFICATION; DRUG DNA BINDING; EPIDERMIS; FEMALE; ISOMER; MOUSE; MUTAGENICITY; NONHUMAN; SKIN CANCER;

ANIMALS; AUTORADIOGRAPHY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; DNA ADDUCTS; EPIDERMIS; FEMALE; MICE; MUTAGENS; PHENANTHRENES; PHOSPHORUS RADIOISOTOPES; SKIN NEOPLASMS; STEREOISOMERISM;

EID: 0029981532     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx950148+     Document Type: Article

References (27)

1. Harvey, R. G. (1991) Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity, Cambridge University Press, Cambridge, England.
2. Jerina, D. M., Chadha, A., Cheh, A. M., Schurdak, M. E., Wood, A. W., and Sayer, J. M. (1990) Covalent bonding of bay-region diol epoxides to nucleic acids. Adv Exp. Med. Biol. 283, 533-553.
3. Dipple, A., Moschel, R. C., and Bigger, C. A. H. (1984) Polynuclear aromatic carcinogens. In Chemical Carcinogens (Searle, C. E , Ed.) pp 41-163, American Chemical Society Monograph 182, American Chemical Society, Washington, DC.
4. 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 benzole[c]phenanthrene bay region diol epoxides on mouse skin. Cancer Res. 40, 3910-3914.
5. Jerina, D. M., Sayer, J. M., Yagi, H., Croisy-Delcey, M., Ittah, Y., Thakker, D. R., Wood, A. W., Chang, R. L., Levin, W., and Conney, A. H. (1982) Highly tumorigenic bay-region diol epoxides from the weak carcinogen benzo[c]phenanthrene. In Biological Reactive Intermediates IIA (Adv. Exp. Med. Biol.) (Snyder, R., Parke, D. V., Kocsis, J. J., Jollow, D. J., Gibson, C. G., and Witmer, C. M., Eds.) pp 501-523, Plenum Press, New York.
6. 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.
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. Seidman, M. M., Dixon, K., Razzaque, A., Zagursky, R. J , and Berman, M. L. (1985) A shuttle vector plasmid for studying carcinogen-induced point mutations in mammalian cells. Gene 38, 233-237.
9. Bigger, C A. H., St. John, J., Yagi, H., Jerina, D. M., and Dipple, A. (1992) Mutagenic specificities of four stereoisomeric benzo[c]phenanthrene dihydrodiol epoxides. Proc. Natl Acad Sci. U.S.A. 89, 368-372.
10. Jerina, D M., Sayer, J. M., Agarwal, S. K., Yagi, H., Levin, W., Wood, A. W., Conney, A. H., Pruess-Schwartz, D., Baird, W. M., Pigott, M. A., and Dipple, A. (1986) Reactivity and tumorigenicity of bay-region diol epoxides derived from polycyclic aromatic hydrocarbons. In Biological Reactive Intermediates III (Kocsis, J. J., Jollow, D. J., Witmer, C. M., Nelson, J. O., and Snyder, R., Eds ) pp 11-30, Plenum Press, New York.
11. Reddy, M. V , and Randerath, K. (1986) Nuclease P1-mediated enhancement of sensitivity of 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis 7, 1543-1551.
12. 32P-postlabeling assay. Chem Res. Toxicol. 5, 685-690.
13. 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.
14. 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.
15. 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 327, 535-536.
16. Dipple, A., and Pigott, M. A. (1987) Resistance of 7,12-dimethylbenz[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-dimethylbenz[a]anthracene to DNA in mouse embryo cell cultures. Cancer Res. 43, 3212-3218.
18. Pelling, J. C., and Slaga, T. J. (1982) Comparison of levels of benzo[a]pyrene diol epoxide diastereomers covalently bound in vivo to macromolecular components of the whole epidermis versus the basal cell layer. Carcinogenesis 3, 1135-1141.
19. Yuspa, S. H., and Harris, C. C. (1974) Altered differentiation of mouse epidermal cells treated with retinyl acetate in vitro. Exp. Cell Res. 86, 95-105.
20. Jeffrey, A. M., Weinstein, I. B., Jennette, K. W., Grzeskowiak, K., Nakanishi, K., Harvey, R. G , Autrup, H., and Harris, C. C. (1977) Structures of benzo[a]pyrene - nucleic acid adducts formed in human and bovine bronchial explants. Nature 269, 348-350.
21. Bigger, C. A. H., Sawicki, J. T., Blake, D. M., Raymond, L. G., and Dipple, A. (1983) Products of binding of 7,12-dimethylbenz[a]anthracene to DNA in mouse skin. Cancer Res. 43, 5647-5651.
22. Pigott, M., and Dipple, A. (1988) 7,12-Dimethylbenz[a]anthracene-DNA adducts in mouse skin, dermis and epidermis. Cancer Lett. 40, 291-297.
23. 32P-postlabeling Chem Res Toxicol. 8, 591-599.
24. Butch, E. R., Lau, H. H. S., Shaw, K. L., Smolarek, T. A., Schmerold, I., Anderson, J. N., Baird, W. M., Yagi, H., and Jerina, D. M. (1992) High selectivity of polyclonal antibodies against DNA modified by diastereomeric benzo[c]phenanthrene 3,4-diol 1,2-epoxides. Carcinogenesis 13, 895-899.
25. Baer-Dubowska, W., Nair, R. V., Cortez, C., Harvey, R. G., and DiGiovanni, J. (1995) Covalent DNA adducts formed in mouse epidermis from dibenz[a,J]anthracene: evidence for the formation of polar adducts. Chem. Res. Toxicol. 8, 292-301.
26. Carothers, A. M., Zhen, W., Mucha, J., Zhang, Y.-J., Santella, R. M., Grunberger, D., and Bohr, V. A. (1992) DNA strand-specific repair of (±)-3α,4β-dihydroxy-1α,2α-epoxy-1,2,3,4- tetrahydrobenzo[c]phenanthrene adducts in the dihydrofolate reductase gene. Proc. Natl. Acad. Sci. U.S.A. 89, 11925-11929.
27. 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.