Formation of a major DNA adduct of the mitomycin metabolite 2,7-diaminomitosene in EMT6 mouse mammary tumor cells treated with mitomycin C

Oncology Research

Volumn 10, Issue 10, 1998, Pages 509-521

  Palom, Yolanda ^a   Belcourt, Michael F ^b,d   Suresh Kumar, Gopinatha ^a,e   Arai, Hitoshi ^c   Kasai, Masaji ^c   Sartorelli, Alan C ^b   Rockwell, Sara ^b   Tomasz, Maria ^a,b  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c KYOWA HAKKO KOGYO CO LTD   (Japan)

^d 4 Science Park   (United States)

^e INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

2,7 Diaminomitosene; DNA adducts; Mitomycin C; Tumor cells

Indexed keywords

2,7 DIAMINOMITOSENE; 2,7-DIAMINOMITOSENE; MITOMYCIN; NUCLEIC ACID SYNTHESIS INHIBITOR;

ANIMAL; ARTICLE; BIOSYNTHESIS; CELL CULTURE; DNA ADDUCT; DNA DAMAGE; DOSE RESPONSE; EXPERIMENTAL NEOPLASM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; MOUSE; TIME;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA ADDUCTS; DNA DAMAGE; DOSE-RESPONSE RELATIONSHIP, DRUG; MAMMARY NEOPLASMS, ANIMAL; MICE; MITOMYCIN; MITOMYCINS; NUCLEIC ACID SYNTHESIS INHIBITORS; TIME FACTORS; TUMOR CELLS, CULTURED;

EID: 0032242916     PISSN: 09650407     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (42)

1. Verweij, J.;Pinedo, H. M. Mitomycin C. In:Pinedo, H. M.;Chabner, B. A.;Longo, D. L., eds. Cancer chemotherapy and biological modifiers, annual 11. Amsterdam: Elsevier Science Publishers B. V.;1990:67-73.
2. Tomasz, M.;Palom, Y. The mitomycin bioreductive antitumor agents: Cross-linking and alkylation of DNA as the molecular basis of their activity. Pharmacol. Ther. 76:73-87; 1997.
3. Suresh Kumar, G.;Lipman, R.;Cummings, J.;Tomasz, M. Mitomycin C-DNA adducts generated by DT-diaphorase. Revised mechanism of the enzymatic reductive activation of mitomycin C.Biochemistry 36:14128-14136; 1997.
4. Sartorelli, A. C.;Hodnick, W. F.;Belcourt, M. F.;Tomasz, M.;Haffty, B.;Fischer, J. J.;Rockwell, S. Mitomycin C: A prototype bioreductive agent.Oncol. Res. 6:501-508; 1994.
5. Belcourt, M. F.;Hodnick, W. F.;Rockwell, S.;Sartorelli, A. C. Bioactivation of mitomycin antibiotics by aerobic and hypoxic Chinese hamster ovary cells overexpressing DT-diaphorase.Biochem. Pharmacol. 51:1669-1678; 1996.
6. Belcourt, M. F.;Hodnick, W. F.;Rockwell, S.;Sartorelli, A. C. Differential toxicity of mitomycin C and porfiromycin to aerobic and hypoxic Chinese hamster ovary cells overexpressing human NADPH: Cytochrome c (P-450) reductase.Proc. Natl. Acad. Sci. USA 93:456-466; 1996.
7. Belcourt, M. F.;Hodnick, W. F.;Rockwell, S.;Sartorelli, A. C. The intracellular location of NADPH: Cytochrome b5 reductase modulates the cytotoxicity of the mitomycins to Chinese hamster ovary cells.J. Biol. Chem. 273:8875-8881; 1998.
8. Kennedy, K. A.;Rockwell, S.;Sartorelli. A. C. Preferential activation of mitomycin C to cytotoxic metabolites by hypoxic tumor cells.Cancer Res. 40:2356-2360; 1980.
9. Kennedy, K. A.;Teicher, B. A.;Rockwell, S.;Sartorelli, A. C. The hypoxic tumor cell: A target for selective cancer chemotherapy.Biochem. Pharmacol. 29:1-8; 1980.
10. Rockwell, S. Hypoxia-directed drugs: Use with irradiation. In:Rosenthal, C. J., ed. Infusion chemotherapy radiation interaction.New York: Elsevier; 1998:77-90.
11. Haffty, B. G.;Son, Y. H.;Sasaki, C. T.;Weissberg, J. B.;Fischer, D. B.;Rockwell, S.;Sartorelli, A. C.;Fischer, J. J. Chemotherapy as an adjunct to radiation in the treatment of squamous cell carcinoma of the head and neck: Results of the Yale mitomycin clinical trials.J. Clin. Oncol. 15:268-276; 1997.
12. Brown, J. M. SR 4233 (tirapazamine): A new anticancer drug exploiting hypoxia in solid tumors.J. Clin. Oncol. 67:1163-1170; 1993.
13. Hendricks, H. R.;Pizao, P. E.;Berger, D. P.;Kooistra, K. L.;Bibby, M. C.;Boven, E.;Meulen, H. C. D-V. D.;Henrar, R. E. C.;Fiebig, H. H.;Double, J. A.;Hornstra, H. W.;Pinedo, H. M.;Workman, P.;Schwartsmann, G. EO9: A novel bioreductive alkylating indoloquinone with preferential solid tumor activity and lack of bone marrow toxicity in preclinical models.Eur. J. Cancer 29A:897-906; 1993.
14. Bizanek, R.;Chowdary, D.;Arai, H.;Kasai, M.;Hughes C. S.;Sartorelli, A. C.;Rockwell, S.;Tomasz, M. Adducts of mitomycin C and DNA in EMT6 mouse mammary tumor cells: Effects of hypoxia and dicumarol on adduct patterns.Cancer Res. 53:5127-5134; 1993.
15. Tomasz, M.;Chowdary, R.;Lipman, R.;Shimotakahara, S.;Veiro, D.;Walker, B.;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.
16. Tomasz, M.;Lipman, R.;Chowdary, D.;Pawlak, J.;Verdine, G. L.;Nakanishi, K. Isolation and structure of a covalent cross-link adduct between mitomycin C and DNA.Science 235:1204-1208; 1987.
17. Bizanek, R.;McGuiness, B. F.;Nakanishi, K.;Tomasz, M. Isola-tion and structure of an interstrand cross-link adduct of mitomycin C and DNA.Biochemistry 31:3084-3091; 1992.
18. Tomasz, M.;Lipman, R.;McGuiness, B. F.;Nakanishi, K. Isolation and characterization of a major adduct between mitomycin C and DNA.J. Am. Chem. Soc. 110:5892-5896; 1988.
19. Brendel, M.;Ruhland, A. Relationships between functionality and genetic toxicity of selected DNA-damaging agents.Mutat. Res. 133:51-85; 1984.
20. Kim, S. Y.;Rockwell, S. Cytotoxic potential of monoalkylation products between mitomycins and DNA: Studies of decarbamoyl mitomycin C in wild type and repair-deficient cell lines.Oncol. Res. 7:39-47; 1995.
21. Pan, S.;Yu, F.;Hipsher, C. Enzymatic and pH modulation of mitomycin C-induced DNA damage in mitomycin C-resistant HCT 116 human colon cancer cells.Mol. Pharmacol. 43:870-877; 1993.
22. 32P-postlabeling: Time course for formation and removal of adducts and biochemical modulation.Cancer Res. 58:453-461; 1998.
23. Lipman, R.;Tomasz, M. Reductive metabolism and alkylation activity of mitomycin C induced by rat liver microsomes.Biochemistry 20:5056-5061; 1981.
24. Schiltz, P.;Kohn, H. Reductively activated mitomycin C: An efficient trapping reagent for electrophiles.J. Am. Chem. Soc. 114: 7958-7959; 1992.
25. Chirrey, L.;Cummings, J.;Halben, G. W.;Smyth, J. F. Conversion of mitomycin C to 2,7-diaminomitosene and 10-decarbamoyl 2,7-diaminomitosene in tumor tissue in vivo.Cancer Chemother. Pharmacol. 35:318-322; 1995.
26. 3H] mitomycin C. J. Labelled Compd. Radiopharm. 28:903-908; 1991.
27. Tomasz, M.;Lipman, R.;Verdine, G. L.;Nakanishi, K. Reassignment of the guanine-binding mode of reduced mitomycin C.Biochemistry 25:4337-4344; 1986.
28. Suresh Kumar, G.;Musser, S. M.;Cummings, J.;Tomasz, M. 2,7-Diaminomitosene, a monofunctional mitomycin C derivative, alkylates DNA in the major groove. Structure and base-sequence specificity of the DNA adduct and mechanism of the alkylation.J. Am. Chem. Soc. 118:9209-9217; 1996.
29. Keyes, S. R.;Loomis, R.;DiGiovanna, M. P.;Pritsos, C. A.;Rockwell, S.;Sartorelli, A. Cytotoxicity and DNA cross-links produced by mitomycin analogs in aerobic and hypoxic EMT6 cells. Cancer Commun. 3:351-356; 1991.
30. Pan, S.;Iracki, T.;Bachur, N. R. DNA alkylation by enzyme-activated mitomycin C.Mol. Pharmacol. 29:622-628; 1986.
31. Tomasz, M.;Chawla, A. K.;Lipman, R. Mechanism of monofunctional and bifunctional alkylation of DNA by mitomycin C.Biochemistry 27:3182-3187; 1988.
32. Prakash, A. S.;Beall, H.;Ross, D.;Gibson, N. W. Sequence-selective alkylation and cross-linking induced by mitomycin C upon activation by DT-diaphorase.Biochemistry 32:5518-5525; 1993.
33. Johnson, D. A.;August, P. R.;Schackleton, C.;Liu, H.;Sherman, D. H. Microbial resistance to mitomycins involves a redox relay mechanism.J. Am. Chem. Soc. 119:2576-2577; 1997.
34. Pan, S. Porfiromycin disposition in oxygen-modulated P388 cells.Cancer Chemother. Pharmacol. 27:187-193; 1990.
35. Peterson, D. M.;Fischer, J. Auto-catalytic quinone methide formation from mitomycin C.Biochemistry 25:4077-4084; 1986.
36. Hoey, B. M.;Butler, J.;Swallow, A. J. Reductive activation of mitomycin C.Biochemistry 27:2608-2614; 1988.
37. Siegel, D.;Beall, H.;Senekowitsch, C.;Kasai, M.;Arai, H.;Gibson, N. W.;Ross, D. Bioreductive activation of mitomycin C by DT-diaphorase.Biochemistry 31:4077-4084; 1986.
38. Iyengar, B. S.;Dorr, R. T.;Shipp, N. G.;Remers, W. A. Alkylation of DNA by C-10 of 2,7-diaminomitosene.J. Med. Chem. 33:253-257; 1990.
39. He, Q-Y. Mechanism of bioactivation and DNA cross-linking activity of new mitomycin analogs. Dissertation, City University of New York; 1994.
40. Maliepaard, M. Mitosenes and related antitumor drugs: Rational design of cytostatic agents (Medical Intelligence Unit). Georgetown, TX: R. G. Landes Company; 1996:101-120.
41. Ramos, L. A.;Lipman, R.;Tomasz, M.;Basu, A. K. The major mitomycin C-DNA monoadduct is cytotoxic but not mutagenic in E. coli.Chem. Res. Toxicol. 11:64-69; 1998.
42. 32P-postlabeling method for detecting unstable N-7-substituted deoxyguanosine adducts in DNA.Proc. Natl. Acad. Sci. USA 91:7232-7236; 1994.