Adducts of Mitomycin C and DNA in EMT6 Mouse Mammary Tumor Cells: Effects of Hypoxia and Dicumarol on Adduct Patterns

Cancer Research

Volumn 53, Issue 21, 1993, Pages 5127-5134

  Bizanek, Roland ^a   Chowdary, Dondapati ^a   Arai, Hitoshi ^c   Kasai, Masaji ^c   Hughes, Christine S ^b   Sartorelli, Alan C ^b   Rockwell, Sara ^b   Tomasz, Maria ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b YALE CANCER CENTER   (United States)

^c KYOWA HAKKO KOGYO CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DICOUMAROL; DNA; MITOMYCIN C; OXIDOREDUCTASE;

ANIMAL CELL; ARTICLE; BREAST TUMOR; CYTOTOXICITY; DNA ADDUCT; DNA CROSS LINKING; ENZYME ACTIVATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYPOXIA; MOUSE; NONHUMAN; PRIORITY JOURNAL;

AEROBIOSIS; ANIMAL; CELL HYPOXIA; CELL LINE; CELL SURVIVAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DICUMAROL; DNA; DNA, NEOPLASM; MAMMARY NEOPLASMS, EXPERIMENTAL; MICE; MITOMYCIN; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.; THIOSULFATES; TRITIUM; TUMOR CELLS, CULTURED;

EID: 0027428318     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: None     Document Type: Article

References (45)

1. Verweij, J. and Pinedo, H. M. Mitomycin C. In: H. M. Pinedo, B. A. Chabner and D. L. Longo (eds.), Cancer Chemotherapy and Biological Modifiers, Annual 11, pp. 67-73. Amsterdam: Elsevier Science Publishers B. V. 1990.
2. Szybalski, W. and Iyer, B. N. Cross-linking of DNA by enzymatically or chemically activated mitomycins and porfiromycins, bifunctionally “alkylating” antibiotics. Fed. Proc., 23: 946-957, 1964.
3. Lin, A. J., Cosby, L. A. and Sartorelli, A. C. Potential bioreductive alkylating agents. In: A. C. Sartorelli (ed.), Cancer Chemotherapy, pp. 71-86. Washington, D.C.: American Chemical Society, 1976.
4. Kennedy, K. A., Rockwell, S. and Sartorelli, A. C. Preferential activation of mitomycin C to cytotoxic metabolites of hypoxic tumor cells. Cancer Res., 40: 2356-2360, 1980.
5. Rockwell, S. and Sartorelli, A. C. Mitomycin C and radiation. In: B. T. Hill and A. S. Bellamy (eds.), Interactions between Antitumor Drugs and Radiation, pp. 125-139. New York: CRC Press, 1990.
6. Kohn, K. W., Molecular mechanisms of cross-linking by alkylating agents and platinum complexes. In: A. C. Sartorelli, J. S., Lazo, and J. R. Bertino (eds.), Molecular Actions and Targets for Cancer Chemotherapeutic Agents, pp. 3-16. New York: Academic Press, Inc. 1981.
7. Hansson, J., Lewensohn, R., Ringborg, U. and Nilsson, B. Formation and removal of DNA cross-links induced by melphalan and nitrogen mustard in relation to drug-induced cytotoxicity in human melanoma cells. Cancer Res., 47: 2631-2637, 1987.
8. Keyes, S. R., Loomis, R., DiGiovanna, M. P., Pritsos, C. A., Rockwell, S. and Sartorelli, A. C., Cytotoxicity and DNA cross-links produced by mitomycin analogs in aerobic and hypoxic EMT6 cells. Cancer Commun., 3: 351-356, 1991.
9. Tomasz, M., Lipman, R., Chowdary, D., Pawlak, J., Verdine, G. L. and Nakanishi, K., Isolation and structure of a covalent cross-link adduct between mitomycin C and DNA. Science (Washington DC), 235: 1204-1208, 1987.
10. Bizanek, R., McGuiness, B. F., Nakanishi, K. and Tomasz, M. Isolation and structure of an intrastrand cross-link adduct of mitomycin C and DNA. Biochemistry, 31: 3084-3091, 1992.
11. Tomasz, M., Lipman, R., McGuiness, B. F. and Nakanishi, K. Isolation and characterization of a major adduct between mitomycin C and DNA. J. Am. Chem. Soc., 110: 5892-5896, 1988.
12. Tomasz, M., Chowdary, R., Lipman, R., Shimotakahara, S., Veiro, D., Walker, B. and Verdine, G. L. Reaction of DNA with chemically or enzymatically activated mitomycin C: isolation and structure of a major covalent adduct. Proc. Natl. Acad. Sci. USA, 83: 6702-6704, 1986.
13. Borowy-Borowski, H., Lipman, R. and Tomasz, M. Recognition between mitomycin C and specific DNA sequences for cross-link formation. Biochemistry, 29: 2999-3006, 1990.
14. Norman, D., Live, D., Sastry, M., Lipman, R., Hingerty, B. E., Tomasz, M., Broyde, S. and Patel, D. J. NMR and computational characterization of mitomycin cross-linked to adjacent deoxyguanosines in the minor groove of the d(T-A-C-G-T-A).d-(T-A-C-G-T-A) duplex. Biochemistry, 29: 2861-2875, 1990.
15. Ludlum, D. High-performance liquid chromatographic separation of DNA adducts induced by cancer chemotherapeutic agents. Pharmacol. Ther., 34: 145-153, 1987.
16. Fracasso, P. M. and Sartorelli, A. C. Cytotoxicity and DNA lesions produced by mitomycin C and porfiromycin in hypoxic and aerobic EMT6 and Chinese hamster ovary cells. Cancer Res., 46: 3939-3944, 1986.
17. Marshall, R. S. and Rauth, A. M. Modification of the cytotoxic activity of mitomycin C by oxygen and ascorbic acid in Chinese hamster ovary cells and a repair-deficient mutant. Cancer Res., 46: 2709-2713, 1986.
18. 3H]-porfiromycin adducts of EMT6 mouse mammary cell DNA: effects of hypoxia and dicumarol on adduct patterns. Cancer Commun., 3: 213-223, 1991.
19. Pan, S., Porfiromycin disposition in oxygen modulated P388 cells. Cancer Chemother. Pharmacol., 27: 187-193, 1990.
20. 3H] mitomycin C. J. Labelled Compd. Radiopharm., 28: 903-908, 1991.
21. Doroshow, J. H., Reductive activation of mitomycin C: a delicate balance. J. Nat. Cancer Inst., 84: 1138-1139, 1992.
22. Rockwell, S., Keyes, S. R. and Sartorelli, A. C. Preclinical studies of porfiromycin as an adjunct to radiotherapy. Radiat. Res., 116: 100-113, 1988.
23. Tomasz, M., Chawla, A. K. and Lipman, R. Mechanism of monofunctional and Afunctional alkylation of DNA by mitomycin C. Biochemistry, 27:3182-3187,1988.
24. Tomasz, M., Lipman, R., Verdine, G. L. and Nakanishi, K. Reassignment of the guanine-binding mode of reduced mitomycin C. Biochemistry, 25: 4337-4344,1986.
25. Kumar, S., Lipman, R. and Tomasz, M. Recognition of specific DNA sequences by mitomycin C for alkylation. Biochemistry, 31: 1399-1407, 1992.
26. McGuiness, B. F., Lipman, R., Nakanishi, K. and Tomasz, M. Reaction of sodium dithionite activated mitomycin C with guanine at non-cross-linkable sequences of oligonucleotides. J. Org. Chem., 56: 4826-4829, 1991.
27. 32P-Labeling test for DNA damage. Proc. Natl. Acad. Sci. USA, 78: 6126-6129, 1981.
28. 32P-Analysis of DNA adducts in somatic and reproductive tissues of rats treated with the anticancer antibiotic, mitomycin C. Mutat. Res., 179: 75-88, 1987.
29. 32P-post labeling analysis. Mutat. Res., 202: 85-91, 1988.
30. Singer, B. and Grunberger, D. Reactions of directly acting agents with nucleic acids. In: Molecular Biology of Mutagens and Carcinogens, Chap. IV, pp. 45-96. New York: Plenum Publishing Corp. 1983.
31. Chowdary, D. Isolation and identification of the adducts of mitomycin C and porfiromycin with DNA formed in vitro and in vivo (Dissertation). New York: The City University of New York, 1989.
32. Eastman, A. and Schulte, N. Enhanced DNA repair as a mechanism of resistance to cis-diamminedichloroplatinum(II). Biochemistry, 27: 4730-4734, 1988.
33. Keyes, S. R., Rockwell, S. and Sartorelli, A. C. Enhancement of mitomycin C cytotoxicity to hypoxic tumor cells by dicumarol in vivo and in vitro. Cancer Res., 45: 213-216, 1985.
34. Rockwell, S., Keyes, S. R. and Sartorelli, A. C. Modulation of the cytotoxicity of mitomycin C to EMT6 mouse mammary cells by dicumarol in vitro. Cancer Res., 48: 5471-5474, 1988.
35. Kennedy, K. A., Teicher, B. A., Rockwell, S. and Sartorelli, A. C. The hypoxic tumor cell: a target for selective cancer chemotherapy. Biochem. Pharmacol. 22:1-8,1980.
36. Siegel, D., Gibson, N. W., Preusch, P. C. and Ross, D. Metabolism of mitomycin C by DT-diaphorase: role in mitomycin C-induced DNA damage and cytotoxicity in human colon carcinoma cells. Cancer Res., 50: 7483-7489, 1990.
37. Gustafson, D. L. and Pritsos, C. A. Bioactivation of mitomycin C by xanthine dehydrogenase from EMT6 mouse mammary carcinoma tumors. J. Natl. Cancer Inst., 84: 1180-1185, 1990.
38. Siegel, D., Beall, H., Senekowitsch, C., Kasai, M., Arai, H., Gibson, N. W. and Ross, D. Bioreductive activation of mitomycin C by DT-diaphorase. Biochemistry, 31: 7879-7885, 1992.
39. Keyes, S. R., Fracasso, P. M., Heimbrook, D. C., Rockwell, S., Sligar, S. G. and Sartorelli, A. C. Role of NADPH: cytochrome c reductase and DT-diaphorase in the biotransformation of mitomycin C. Cancer Res., 44: 5638-5643, 1984.
40. Marshall, R. S., Paterson, M. C. and Rauth, A. M. Deficient activation by a human cell strain leads to mitomycin C resistance under aerobic but not hypoxic conditions. Br. J. Cancer., 59: 341-346, 1989.
41. Begleiter, A., Robotham, E. and Leith, M. Role of NAD(P)H:(quinone acceptor) oxidoreductase (DT-diaphorase) in activation of mitomycin C under hypoxia. Mol. Pharmacol., 41: 677-682, 1992.
42. Dulhanty, A. M. and Whitmore, G. F. Chinese hamster ovary cell lines resistant to mitomycin C under aerobic but not hypoxic conditions are deficient in DT-diaphorase. Cancer Res., 57: 1860-1865, 1991.
43. Gustafson, D. L. and Pritsos, C. A. Enhancement of xanthine dehydrogenase mediated mitomycin C metabolism by dicumarol. Cancer Res., 52: 6936-6939, 1992.
44. Hodnick, W. F. and Sartorelli, A. C. Reductive activation of mitomycin C by NADH-cytochrome b5 reductase. Proc. Am. Assoc. Cancer Res., 32: 397, 1991.
45. 3H]-mitomycin C and DNA formed in EMT6 mouse mammary tumor cells. Proc. Am. Assoc. Cancer Res., 33: 402, 1992.