DNA adduct of the mitomycin C metabolite 2,7-diaminomitosene is a nontoxic and nonmutagenic DNA lesion in vitro and in vivo

Chemical Research in Toxicology

Volumn 18, Issue 2, 2005, Pages 213-223

  Utzat, Christopher D ^a   Clement, Cristina C ^b   Ramos, Leilani A ^a   Das, Arunangshu ^b,c   Tomasz, Maria ^b   Basu, Ashis K ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b CITY UNIVERSITY OF NEW YORK   (United States)

^c PENN STATE COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,7 DIAMINOMITOSENE; 2,7 DIAMINOMITOSENE DEOXYGUANINE; CYTOSINE DERIVATIVE; DEOXYGUANOSINE; DNA DIRECTED DNA POLYMERASE ETA; DNA FRAGMENT; DNA POLYMERASE; DRUG METABOLITE; GUANINE; KLENOW DNA POLYMERASE; MITOMYCIN C; MITOMYCIN C DEOXYGUANINE; MITOMYCIN C DERIVATIVE; OLIGONUCLEOTIDE; PRIMER DNA; T7 DNA POLYMRASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BACTERIOPHAGE M13; CELL FREE SYSTEM; CELL STRAIN COS7; CELL VIABILITY; CONTROLLED STUDY; DNA ADDUCT; DNA ALKYLATION; DNA CROSS LINKING; DNA REPLICATION; DNA STRAND; DRUG ACTIVATION; DRUG STRUCTURE; ESCHERICHIA COLI; GENE INSERTION; MUTAGEN TESTING; MUTATION RATE; NONHUMAN; PHAGEMID; PHAGEMID MS2; REDUCTION; SHUTTLE VECTOR; THERMOSTABILITY;

ANIMALS; COS CELLS; DNA; DNA ADDUCTS; DNA DAMAGE; ESCHERICHIA COLI; MITOMYCIN; MITOMYCINS; MOLECULAR STRUCTURE; MUTAGENICITY TESTS; OLIGONUCLEOTIDES;

EID: 13844269362     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx049813h     Document Type: Article

References (33)

1. Carter, S. K., and Crooke, S. T. (1979) Mitomycin C, Current Status and New Developments, Academic Press, New York.
2. Chirrey, L., Cummings, J., Halbert, G. W., and Smyth, J. F. (1995) 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.
3. Tomasz, M., and Lipman, R. (1984) Reductive metabolism and alkylation activity of mitomycin C induced by rat liver microsomes. Biochemistry 20, 5056-5061.
4. Tomasz, M. (1995) Mitomycin C: Small, fast and deadly (but very selective). Chem. Biol. 2, 575-579.
5. Szybalski, W., and Iyer, V. N. (1967) In Antibiotics I: Mechanism of Action (Gottlieb, D., and Shaw, P. D., Eds) p 230, Springer-Verlag, New York.
6. Suresh Kumar, G., Lipman, R., Cummings, J., and Tomasz, M. (1997) Mitomycin C DNA adducts generated by DT-diaphorase. Revised mechanism of the enzymatic reductive activation of mitomycin C. Biochemistry 36, 14128-14136.
7. Palom, Y., Belcourt, M. F., Musser, S. M., Sartorelli, A. C., Rockwell, S., and Tomasz, M. (2000) Structure of adduct X, the last unknown of the six major DNA adducts of mitomycin C formed in EMT6 mouse mammary tumor cells. Chem. Res. Toxicol. 13, 479-488.
8. Suresh Kumar, G., Musser, S. M., Cummings, J., and Tomasz, M. (1996) 2,7-Diaminomitosene, a monofunctional mitomycin derivative alkylates DNA in the major groove. Structure and basesequence specificity of the DNA adduct and mechanism of the alkylation. J. Am. Chem. Soc. 118, 9209-9217.
9. Palom, Y., Belcourt, M. F., Suresh Kumar, G., Arai, H., Kasai, M., Sartorelli, A. C., Rockwell, S., and Tomasz, M. (1998) Formation of a major DNA adduct of the mitomycin metabolite 2,7-diaminomitosene in EMT6 mouse mammary tumor cells treated with mitomycin C. Oncol. Res. 10, 509-521.
10. Palom, Y., Belcourt, M. F., Tang, L.-Q, Mehta, S. S., Sartorelli, A. C., Pritsos, C. A., Pritsos, K. L., Rockwell, S., and Tomasz, M. (2001) Bioreductive metabolism of mitomycin C in EMT6 mouse mammary tumor cells: Cytotoxic and noncytotoxic pathways, leading to different types of DNA adducts. The effect of dicumarol. Biochem. Pharmacol. 61, 1517-1529.
11. Busby, W. F., Jr., and Wogan, G. N. (1984) Aflatoxins. In Chemical Carcinogens (Searle, C., Ed.) 2nd ed., pp 945-1136, American Chemical Society, Washington, DC.
12. Hurley, L. H., and Needham-vanDevanter, D. R. (1986) Covalent binding of antitumor antibiotics in the minor groove of DNA. Mechanism of action of CC-1065 and the pyrrolo(1,4)benzodiazepines. Acc. Chem. Res. 19, 230-237.
13. Basu, A. K., Hanrahan, C. J., Malia, S. A., Kumar, S., Bizanek, R., and Tomasz, M. (1993) Effect of site-specifically located mitomycin C-DNA monoadducts on in vitro DNA synthesis by DNA polymerases. Biochemistry 32, 4708-4718.
14. Ramos, L. A., Lipman, R., Tomasz, M., and Basu, A. K. (1998) The major mitomycin C-DNA monoadduct is cytotoxic but not mutagenic in Escherichia coli. Chem. Res. Toxicol. 11, 64-69.
15. Subramaniam, G., Paz, M. M., Suresh Kumar, G., Das, A., Palom, Y., Clement, C. C., Patel, D. J., and Tomasz, M. (2001) Solution structure of a guanine-N7-linked complex of the mitomycin C metabolite 2,7-diaminomitosene and DNA. Basis of sequence selectivity. Biochemistry 40, 10473-10484.
16. Bacolod, M. D., Krishnasamy, R., and Basu, A. K. (2000) Mutagenesis of N-(deoxyguanosin-8-yl)-1-aminopyrene in a nonrepetitive CGC sequence in Escherichia coli. Chem. Res. Toxicol. 13, 523-528.
17. 6-Ethenodeoxyadenosine, a DNA adduct highly mutagenic in mammalian cells. Biochemistry 35, 11487-11492.
18. Kunkel, T. A. (1984) Mutational specificity of depurination. Proc. Natl. Acad. Sci. U.S.A. 81, 1494-1498.
19. Lawrence, C. W., Borden, A., Banerjee, S. K., and LeClerc, J. E. (1990) Mutation frequency and spectrum resulting from a single abasic site in a single-stranded vector. Nucleic Acids Res. 18, 2153-2157.
20. Palom, Y., Suresh, Kumar, G., Tang, L.-Q., Paz, M. M., Musser, S. M., Rockwell, S., and Tomasz, M. (2002) Relative toxicities of DNA cross-links and monoadducts: New insights from studies of decarbamoyl mitomycin C and mitomycin C. Chem. Res. Toxicol. 15, 1398-1406.
21. Moriya, M. (1993) Single-stranded shuttle phagemid for mutagenesis studies in mammalian cells: 8-oxoguanine in DNA induces targeted G.C → T.A transversions in simian kidney cells. Proc. Natl. Acad. Sci. U.S.A. 90, 1122-1126.
22. Prakash, A. S., Beall, H., Ross, D., and Gibson, N. W. (1993) Sequence-selective alkylation and cross-linking induced by mitomycin C upon activation by DT-diaphorase. Biochemistry 32, 5518-5525.
23. Hartley, J. A., and Wyatt, M. D. (1997) Determination of the DNA sequence specificity of alkylation damage using cleavage-based assays. In Drug-DNA Interaction Protocols, Methods in Molecular Biology (Fox, K. R., Ed.) Vol. 90, pp 147-156, Humana Press, Totowa, NJ.
24. 2. Biochemistry 29, 10438-10448.
25. Kunkel, T. A., Pavlov, Y. I., and Bebenek, K. (2003) Functions of human DNA polymerases, and suggested by their properties, including fidelity with undamaged DNA templates. DNA Repair 2, 135-149.
26. John, D. A., August, P. R., August, P. R., Shackleton, C., Liu, H., and Sherman, D. H. (1997) Microbial resistance to mitomycins involves a redox relay mechanism. J. Am. Chem. Soc. 119, 2576-2577.
27. Sastry, M., Fiala, R., Lipman, R., Tomasz, M., and Patel, D. J. (1995) Solution structure of the monoalkylated mitomycin C-DNA complex. J. Mol. Biol. 247, 338-359.
28. Steitz, T. A., Smerdon, S. J., Jager, J., and Joyce, C. M. (1994) A unified mechanism for nonhomologous DNA and RNA polymerases. Science 266, 2022-2025.
29. 6-guanyl)ethyl]glutathione. Chem. Res. Toxicol. 11, 311-316.
30. Hansen, M. R., and Hurley, L. H. (1996) Pluramycins. Old drugs having modern friends in structural biology. Acc. Chem. Res. 29, 249-258.
31. 1-DNA adduct. Proc. Natl. Acad. Sci. U.S.A. 93, 1535-1539.
32. 2-dG adducts by human DNA polymerases eta and kappa. Mutat. Res. 510, 23-25.
33. Ling, H., Sayer, J. M., Plosky, B. S., Yagi, H., Boudsocq, F., Woodgate, R., Jerina, D. M., and Yang, W. (2004) Crystal structure of a benzo[a]pyrene diolepoxide adduct in a ternary complex with a DNA polymerase. Proc. Natl. Acad. Sci. U.S.A. 101, 2265-2269.