Comparative mouse skin tumorigenicity and induction of Ha-ras mutations by bay region diol epoxides of 5-methylchrysene and 5,6-dimethylchrysene

Carcinogenesis

Volumn 19, Issue 1, 1998, Pages 157-160

  Hecht, Stephen S ^a   Ronai, Zeev A ^b   Dolan, Lisa ^c   Desai, Dhimant ^c   Amin, Shantu ^c  

^a UNIVERSITY OF MINNESOTA   (United States)

^b MOUNT SINAI SCHOOL OF MEDICINE   (United States)

^c AMERICAN HEALTH FOUNDATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARCINOGEN; CHRYSENE DERIVATIVE; DNA; EPOXIDE; POLYCYCLIC AROMATIC HYDROCARBON;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CARCINOGEN DNA INTERACTION; CARCINOGENICITY; CONTROLLED STUDY; FEMALE; GENE MUTATION; MOUSE; MUTATION RATE; NONHUMAN; ONCOGENE H RAS; PRIORITY JOURNAL; SKIN CARCINOGENESIS;

ANIMALS; BAY REGION (CHEMISTRY); CHRYSENES; FEMALE; GENES, RAS; MICE; MUTAGENS; POLYMERASE CHAIN REACTION; SKIN; SKIN NEOPLASMS; TIME FACTORS;

EID: 0031843896     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/19.1.157     Document Type: Article

References (31)

1. Bizub, D., Wood, A.W. and Skalka, A.M. (1986) Mutagenesis of the Haras oncogene in mouse skin tumors induced by polycyclic aromatic hydrocarbons. Proc. Natl Acad. Sci. USA, 83, 6048-6052.
2. Quintanilla, M., Brown, K., Ramsden, M. and Balmain, A. (1986) Carcinogen-specific mutation and amplification of Ha-ras during mouse skin carcinogenesis. Nature, 322, 78-80.
3. Bailleul, R.B., Brown, K., Ramsden, M., Akhurst, R.J., Fee, F. and Balmain, A. (1989) Chemical induction of oncogene mutations and growth factor activity in mouse skin carcinogenesis. Environ. Hlth Perspect., 81, 23-27.
4. Gill, R.D., Beltrán, L., Nettikumara, A.N., Harvey, R.G., Kootstra, A. and DiGiovanni, J. (1992) Analysis of point mutations in murine c-Ha-ras of skin tumors initiated with dibenz[a,j]anthracene and derivatives. Mol. Carcinogenesis, 6, 53-59.
5. Brown, K., Buchmann, A. and Balmain, A. (1990) Carcinogen-induced mutations in the c-Ha-ras gene provide evidence of multiple pathways for tumor progression. Proc. Natl Acad. Sci. USA, 87, 538-542.
6. Colapietro, A.-M., Goodell, A.L. and Smart, R.C. (1993) Characterization of benzo[a]pyrene-initiated mouse skin papillomas for Ha-ras mutations and protein kinase C levels. Carcinogenesis, 14, 2289-2295.
7. DiGiovanni, J., Beltrán, L., Rupp, A., Harvey, R.G. and Gill, R.D. (1993) Further analysis of c-Ha-ras mutations in papillomas initiated by several polycyclic aromatic hydrocarbons and papillomas from uninitiated, promoter-treated skin in SENCAR mice. Mol. Carcinogenesis, 8, 272-279.
8. Ronai, Z.A., Gradia, S., El-Bayoumy, K., Amin, S. and Hecht, S.S. (1994) Contrasting incidence of ras mutations in rat mammary and mouse skin rumors induced by anti-benzo[c]phenanthrene-3,4-diol-1,2-epoxide. Carcinogenesis, 15, 2113-2116.
9. Chakravarti, D., Pelling, J.C., Cavalieri, E.L. and Rogan, E.G. (1995) Relating aromatic hydrocarbon-induced DNA adducts and c-Ha-ras mutations in mouse skin papillomas: the role of apurinic sites. Proc. Natl Acad. Sci. USA, 92, 10422-10426.
10. Munoz, E.F., Diwan, B.A., Calvert, R.J., Weghorst, C.M., Anderson, J., Rice, J.M. and Buzard, G.S. (1996) Transplacental mutagenicity of cisplatin: Ha-ras codon 12 and 13 mutations in skin tumors of SENCAR mice. Carcinogenesis, 17, 2741-2745.
11. Ralston, S.L., Seidel, A., Luch, A., Platt, K.L. and Baird, W.M. (1995) Stereoselective activation of dibenzo[a,l]pyrene to (-)-anti-(11R,12S,13S,14R)-and (+)syn(11S,12R,13S,14R)-11,12-diol-13,14-epoxides which bind extensively to DNA in the human mammary carcinoma cell line MCF-7. Carcinogenesis, 16, 2899-2907.
12. Chadha, A., Sayer, J.M., Yeh, H.J.C., Yagi, H., Cheh, A.M., Pannell, L.K. and Jerina, D.M. (1989) Structures of covalent nucleoside adducts formed from adenine, guanine, and cytosine bases of DNA and the optically active bay-region 3,4-diol 1,2-epoxides of dibenz[a,j]anthracene. J. Am. Chem. Soc., 111, 5456-5463.
13. Cheng, S.C., Prakash, A.S., Pigott, M.A., Hilton, B.D., Lee, H., Harvey, R.G. and Dipple, A. (1988) A metabolite of the carcinogen 7,12-dimethyl-benz[a]anthracene that reacts predominantly with adenine residues in DNA. Carcinogenesis, 9, 1721-1723.
14. 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.
15. Dipple, A. (1994) Reactions of polycyclic aromatic hydrocarbons with DNA. In Hemminki, K., Dipple, A., Shuker, D.E.G., Kadlubar, F.F., Segerbäck, D. and Bartsch, H. (eds) DNA Adducts: Identification and Biological Significance, International Agency for Research on Cancer, Lyon, vol. 125, pp. 107-129.
16. Chen, J.X., Kisleyou, A.S., Harvey, R.G., Slaga, T.J., Morris, R.J. and Tang, M. (1996) Using UvrABC nuclease to detect 7,12-dimethylbenz[a]anthracene anti-diol epoxide-DNA binding specificity in the mouse H-ras gene. Chem. Res. Toxicol., 9, 1350-1354.
17. Pelling, J.C., Neades, R. and Strawhecker, J. (1988) Epidermal papillomas and carcinomas induced in uninitiated mouse skin by tumor promoters alone contain a point mutation in the 61st codon of the Ha-ras oncogene. Carcinogenesis, 9, 665-667.
18. Ha gene. Carcinogenesis, 15, 1975-1978.
19. Misra, B., Amin, S. and Hecht, S.S. (1992) Dimethylchrysene diol epoxides: mutagenicity in Salmonella typhimurium, tumorigenicity in newborn mice, and reactivity with deoxyadenosine in DNA. Chem. Res. Toxicol., 5, 248-254.
20. Szeliga, J., Hilton, D., Chmurny, G.N., Krzeminski, J., Amin, S. and Dipple, A. (1997) Characterization of DNA adducts formed by the four configurationally isomeric 5,6-dimethylchrysene 1,2-dihydrodiol-3,4-epoxides. Chem. Res. Toxicol., 10, 378-385.
21. Reardon, D.B., Prakash, A.S., Hilton, B.D., Roman, J.M., Pataki, J., Harvey, R.G. and Dipple, A. (1987) Characterization of 5-methylchrysene-1,2-dihydrodiol-3,4-epoxide-DNA adducts. Carcinogenesis, 8, 1317-1322.
22. Zacharias, D.E., Kashino, S., Glusker, J.P., Harvey, R.G., Amin, S. and Hecht, S.S. (1984) The bay-region geometry of some 5-methylchrysenes: steric effects in 5,6-and 5,12-dimethylchrysenes. Carcinogenesis, 5, 1421-1430.
23. Hirshfeld, F.L. (1963) The structure of overcrowded aromatic compounds. Part VII. Out of plane deformation in benzo[c]phenanthrene and 1,12-dimethylbenzo[c]phenanthrene. J. Chem. Soc., 2126-2135.
24. Carrell, C.J., Carrell, T.G., Carrell, H.L., Prout, K. and Glusker, J.P. (1997) Benzo[a]pyrene and its analogues: structural studies of molecular strain. Carcinogenesis, 18, 415-422.
25. Amin, S., Camanzo, J., Huie, K. and Hecht, S.S. (1984) Improved photochemical synthesis of 5-methylchrysene derivatives and its application to the preparation of 7,8-dihydro-7,8-dihydroxy-5-methylchrysene. J. Org. Chem., 49, 381-384.
26. Harvey, R.G., Pataki, J. and Lee, H. (1986) Synthesis of the dihydrodiol and diol epoxide metabolites of chrysene and 5-methylchrysene. J. Org. Chem., 51, 1407-1412.
27. Hecht, S.S., Rivenson, A. and Hoffmann, D. (1980) Tumor-initiating activity of dihydrodiols formed metabolically from 5-methylchrysene. Cancer Res., 40, 1396-1399.
28. Amin, S., Desai, D. and Hecht, S.S. (1992) Comparative tumorigenicity of dimethylchrysenes in mouse skin. Chem. Res. Toxicol., 5, 237-241.
29. Misra, B., Amin, S. and Hecht, S.S. (1992) Metabolism and DNA binding of 5,6-dimethylchrysene in mouse skin. Chem. Res. Toxicol., 5, 242-247.
30. 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.
31. Hecht, S.S.,. Radok, L., Amin, S., Huie, K., Melikian, A.A., Hoffmann, D., Pataki, J. and Harvey, R.G. (1985) Tumorigenicity of 5-methylchrysene dihydrodiols and dihydrodiol epoxides in newborn mice and on mouse skin. Cancer Res., 45, 1449-1452.