DNA adduct levels associated with p53 induction and delay of MCF-7 cells in S phase after exposure to benzo[g]chrysene dihydrodiol epoxide enantiomers

Molecular Carcinogenesis

Volumn 23, Issue 2, 1998, Pages 115-120

  Khan, Qasim A ^a   Agarwal, Rajiv ^a   Seidel, Albrecht ^b   Frank, Heinz ^b   Vousden, Karen H ^a   Dipple, Anthony ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

G1 arrest; Mammary carcinogenesis; Polycyclic aromatic hydrocarbon

Indexed keywords

BENZO[G]CHRYSENE 11,12 DIHYDRODIOL 13,14 EPOXIDE; CHRYSENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; PROTEIN P53; UNCLASSIFIED DRUG;

ARTICLE; BREAST CARCINOGENESIS; BREAST CARCINOMA; CANCER CELL CULTURE; CELL CYCLE S PHASE; CONTROLLED STUDY; DNA ADDUCT; HUMAN; HUMAN CELL; PRIORITY JOURNAL; TUMOR SUPPRESSOR GENE;

CHRYSENES; DNA ADDUCTS; HUMANS; S PHASE; STEREOISOMERISM; TUMOR CELLS, CULTURED; TUMOR SUPPRESSOR PROTEIN P53;

EID: 0031792239     PISSN: 08991987     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-2744(199810)23:2<115::AID-MC8>3.0.CO;2-R     Document Type: Article

References (31)

1. Kastan MB, Onyekwere O, Sidransky D, Vogelstein B, Craig RW. Participation of p53 protein in the cellular response to DNA damage. Cancer Res 51:6304-6311, 1991.
2. Kuerbitz SJ, Plunkett BS, Walsh WV, Kastan MB. Wild-type p53 is a cell cycle checkpoint determinant following irradiation. Proc Natl Acad Sci USA 89:7491-7495, 1992.
3. Nelson WG, Kastan MB. DNA strand breaks: The DNA template alterations that trigger p53-dependent DNA damage response pathways. Mol Cell Biol 14:1815-1823, 1994.
4. Plant JE, Roberts JJ. Extension of the pre-DNA synthetic phase of the cell cycle as a consequence of DNA alkylation in Chinese hamster cells: A possible mechanism of DNA repair. Chem Biol Interact 3:343-351, 1971.
5. Fritsche M, Haessler C, Brandner G. Induction of nuclear accumulation of the tumor-suppressor protein p53 by DNA-damaging agents. Oncogene 8:307-318, 1993.
6. Smith ML, Fornace AJ. Mammalian DNA damage-inducible genes associated with growth arrest and apoptosis. Mutat Res 340:109-124, 1996.
7. Levine AJ. p53, the cellular gatekeeper for growth and division. Cell 88:323-331, 1997.
8. Xiong Y, Hannon GH, Zhang H, Casso D, Kobayashi R, Beach D. p21 is a universal inhibitor of cyclin kinases. Nature 366:701-704, 1993.
9. El-Deiry WS, Tokino T, Velculescu VE, et al. WAF1, a potential mediator of p53 tumor suppression. Cell 75:817-825, 1993.
10. Harper JW, Adami GR, Wei N, Keyomarsi K, Elledge SJ. The p21 Cdk-interacting protein Cip1 is a potent inhibitor of G1 cyclin-dependent kinases. Cell 75:805-816, 1993.
11. waf1/cip1. Carcinogenesis 18:2313-2318, 1997.
12. Amin S, Krzeminski J, Rivenson A, Kurtzke C, Hecht SS, El-Bayoumy K. 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, 1995.
13. 32P-postlabeling. Chem Res Toxicol 8:591-599, 1995.
14. Szeliga J, Page JE, Hilton BD, et al. Characterization of DNA adducts formed by anti-benzo[g]chrysene 11,12-dihydrodiol 13,14-epoxide. Chem Res Toxicol 8:1014-1019, 1995.
15. Platt KL, Oesch F. Efficient synthesis of non-K-region-dihydrodiols of polycyclic aromatic hydrocarbons from o-quinones and catechols. Journal of Organic Chemistry 48:256-268, 1983.
16. Bushman DR, Grossman SJ, Jerina DM, Lehr RE. 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. Journal of Organic Chemistry 54:3533-3544, 1989.
17. Glatt H, Piée A, Pauly K, Steinbrecher T, Schrode R, Oesch F, Seidel A. 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, 1991.
18. Kiselyov AS, Lee HM, Harvey RG. Efficient syntheses of the anti-and syn-diol epoxide metabolites of the carcinogenic polycyclic aromatic hydrocarbon benzo[g]chrysene. Journal of Organic Chemistry 60, 6123-6128, 1995.
19. Yagi H, Thakker DR, Ittah Y, Croisy-Delcey M, Jerina DM. Synthesis and assignment of absolute configuration to the trans-3,4-dihydrodiols and 3,4-diol-1,2-epoxides of benzo[c]phenanthrene. Tetrahedron Letters 24:1349-1352, 1983.
20. Agarwal R, Coffing SL, Baird WM, Kiselyov AS, Harvey RG, Dipple A. Metabolic activation of benzo[g]chrysene in the human mammary carcinoma cell line MCF-7. Cancer Res 57:415-419, 1997.
21. Agarwal R, Canella KA, Yagi H, Jerina DM, Dipple A. Benzo[c]phenanthrene-DNA adducts in mouse epidermis in relation to the tumorigenicities of four configurationally isomeric 3,4-dihydrodiol 1,2-epoxides. Chem Res Toxicol 9:586-592, 1996.
22. 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis 7:1543-1551, 1986.
23. waf1 in the human mammary carcinoma cell line MCF-7. Polycyclic Aromatic Compounds 10:299-306, 1996.
24. Venkatachalam S, Denissenko MF, Wani AA. Modulation of (+/-)-anti-BPDE mediated p53 accumulation by inhibitors of protein kinase C and poly(ADP-ribose) polymerase. Oncogene 14:801-809, 1997.
25. Stierum RH, Van Herwijnen MHM, Pasman PC, Hageman GJ, Kleinjans JCS, Van Agen B. Inhibition of poly(ADP-ribose)-polymerase increases (+/-)-anti-benzo[a]pyrene diolepoxide-induced micronuclei formation and p53 accumulation in isolated human peripheral blood lymphocytes. Carcinogenesis 16:2765-2771, 1995.
26. Rämet M, Castrén K, Järvinen K, et al. p53 Protein expression is correlated with benzo[a]pyrene-DNA adducts in carcinoma cell lines. Carcinogenesis 16:2117-2124, 1995.
27. Sizemore N, Mukhtar H, Couch LH, Howard PC, Rorke EA. Differential response of normal and HPV immortalized ectocervical epithelial cells to B[a]P. Carcinogenesis 16:2413-2418, 1995.
28. Tapiainen T, Järvinen K, Pääkkö P, Bjelogrlic N, Vähäkangas K. TPA decreases the p53 response to benzo[a]pyrene-DNA adducts in mouse skin. Carcinogenesis 17:1377-1380, 1996.
29. Bjelogrlic NM, Mäkinen M, Stenbäck F, Vähäkangas K. Benzo[a]pyrene-7,8-diol-9,10-epoxide-DNA adducts and increased p53 protein in mouse skin. Carcinogenesis 15:771-774, 1994.
30. Amin S, Desai D, Dai W, Harvey RG, Hecht SS. Tumorigenicity in newborn mice of fjord region and other sterically hindered diol epoxides of benzo[g]chrysene, dibenzo[a,l]pyrene (dibenzo-[def,p]chrysene), 4H-cyclopenta[def]chrysene and fluoranthene. Carcinogenesis 16:2813-2817, 1995.
31. Levin W, Chang RL, Wood A, et al. 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, 1986.