Mapping DNA adducts of mitomycin C and decarbamoyl mitomycin C in cell lines using liquid chromatography/electrospray tandem mass spectrometry

Chemical Research in Toxicology

Volumn 21, Issue 12, 2008, Pages 2370-2378

  Paz, Manuel M ^a,e   Ladwa, Sweta ^a,f   Champeil, Elise ^b   Liu, Yanfeng ^d   Rockwell, Sara ^d   Boamah, Ernest K ^a   Bargonetti, Jill ^a   Callahan, John ^c   Roach, John ^c   Tomasz, Maria ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b JOHN JAY COLLEGE OF CRIMINAL JUSTICE   (United States)

^c CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

^d YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^e UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^f A2SP Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

MITOMYCIN C;

ANIMAL CELL; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CONTROLLED STUDY; CROSS LINKING; DNA ADDUCT; DNA REPAIR; ELECTROSPRAY MASS SPECTROMETRY; FANCONI ANEMIA; GENE MAPPING; HUMAN; HUMAN CELL; LIQUID CHROMATOGRAPHY; MOUSE; NONHUMAN; QUANTITATIVE ANALYSIS; TUMOR CELL;

ANIMALS; BREAST NEOPLASMS; CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CROSS-LINKING REAGENTS; DNA ADDUCTS; DNA DAMAGE; DNA REPAIR; DNA, NEOPLASM; FIBROBLASTS; HUMANS; MAMMARY NEOPLASMS, ANIMAL; MICE; MITOMYCIN; MITOMYCINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

EID: 58149092958     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx8002615     Document Type: Article

References (44)

1. Verweij, J., den Hartigh, J., and Pinedo, H. M. (1990) Antitumor Antibiotics, J. B. Lippincott Company, Philadelphia, PA.
2. Tomasz, M., and Palom, Y. (1997) The mitomycin bioreductive antitumor agents: Cross-linking and alkylation of DNA as the molecular basis of their activity. Pharmacol. Ther. 76, 73-87.
3. 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.
4. Bizanek, R., Chowdary, D., Arai, H., Kasai, M., Hughes, C. S., Sartorelli, A. C., Rockwell, S., and Tomasz, M. (1993) 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.
5. Tomasz, M., Chowdary, D., Lipman, R., Shimotakahara, S., Veiro, D., Walker, V., and Verdine, G. L. (1986) Reaction of DNA with chemically or enzymatically activated mitomycin C: Isolation and structure of the major covalent adduct. Proc. Natl. Acad. Sci. U.S.A. 83, 6702-6706.
6. Tomasz, M., Lipman, R., Chowdary, D., Pawlak, J., Verdine, G. L., and Nakanishi, K. (1987) Isolation and structure of a covalent cross-link adduct between mitomycin C and DNA. Science 235, 1204-1208.
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. 32P- labeling test for DNA damage. Proc. Natl. Acad. Sci. U.S.A. 78, 6126-6129.
9. Reddy, M. V., and Randerath, K. (1987) 32P-analysis of DNA adducts in somatic and reproductive tissues of rats treated with the anticancer antibiotic, mitomycin C. Mutat. Res. 179, 75-88.
10. Pan, S.-S., Yu, F., and Hipsher, C. (1993) 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.
11. Warren, A. J., Maccubbin, A. E., and Hamilton, J. W. (1998) Detection of mitomycin C-DNA adducts in vivo by 32P-postlabeling: Time course for formation and removal of adducts and biochemical modulation. Cancer Res. 58, 453-461.
12. Warren, A. J., Mustra, D. J., and Hamilton, J. W. (2001) Detection of mitomycin C-DNA adducts in human breast cancer cells grown in culture, as xenografted tumors in nude mice, and in biopsies of human breast cancer patient tumors as determined by 32P-postlabeling. Clin. Cancer Res. 7, 1033-1042.
13. Matsumoto, A., Vos, J.-M. H., and Hanawalt, P. C. (1989) Repair analysis of mitomycin C-induced DNA crosslinking in ribosomal RNA genes in lymphoblastoid cells from Fanconi's anemia patients. Mutat. Res. 217, 185-192.
14. Dorr, R. T., Bowden, G. T., Alberts, D. S., and Liddil, J. D. (1985) Interactions of mitomycin C with mammalian DNA detected by alkaline elution. Cancer Res. 45, 3510-3516.
15. Fracasso, P. M., and Sartorelli, A. C. (1986) 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.
16. Giese, R. W., and Vouros, P. (1993) Methods development toward the measurement of polyaromatic hydrocarbon-DNA adducts by mass spectrometry. Res. Rep. Health Eff. Inst. 1-25.
17. Doerge, D. R., Churchwell, M. I., Marques, M. M., and Beland, F. A. (1999) Quantitative analysis of 4-aminobiphenyl-C8-deoxyguanosyl DNA adducts produced in vitro and in vivo using HPLC-ES-MS. Carcinogenesis 20, 1055-1061.
18. Andrews, C. L., Vouros, P., and Harsch, A. (1999) Analysis of DNA adducts using high-performance separation techniques coupled to electrospray ionization mass spectrometry. J. Chromatogr. A 856, 515-526.
19. Singh, G., Gutierrez, A., Xu, K., and Blair, I. A. (2000) Liquid chromatography/electron capture atmospheric pressure chemical ionization/mass spectrometry: Analysis of pentafluorobenzyl derivatives of biomolecules and drugs in the attomole range. Anal. Chem. 72, 3007-3013.
20. Paehler, A., Richoz, J., Soglia, J., Vouros, P., and Turesky, R. J. (2002) Analysis and quantification of DNA adducts of 2-amino-3,8- dimethylimidazo[4,5-f]quinoxaline in liver of rats by liquid chromatography/electrospray tandem mass spectrometry. Chem. Res. Toxicol. 15, 551-561.
21. Takeiri, A., Mishima, M., Tanaka, K., Shioda, A., Harada, A., Watanabe, K., Masumura, K.-I., and Nohmi, T. (2006) A newly established GDL1 cell line from gpt delta mice well reflects the in vivo mutation spectra induced by mitomycin C. Mutat. Res. 609, 102-115.
22. Budach, W., Paulsen, F., Welz, S., Classen, J., Scheithauer, H., Marini, P., Belka, C., and Bamberg, M. (2002) Mitomycin C in combination with radiotherapy as a potent inhibitor of tumour cell repopulation in a human squamous cell carcinoma. Br. J. Cancer 86, 470-476.
23. Montie, J. E. (2001) Intravesical therapy for bladder cancer: empiricism at the helm. J. Natl. Cancer Inst. 93, 572-573.
24. Zheng, H., Wang, X., Warren, A. J., Legerski, R. J., Nairn, R. S., Hamilton, J. W., and Li, L. (2003) Nucleotide excision repair- and polymerase eta-mediated error-prone removal of mitomycin C interstrand cross-links. Mol. Cell. Biol. 23, 754-761.
25. 3-3H] mitomycin C. J. Labelled Compd. Radiopharm. 28, 903-908.
26. Cao, H., Hearst, J. E., Corash, L., and Wang, Y. (2008) LC-MS/MS for the detection of DNA interstrand cross-links formed by 8-methoxypsoralen and UVA irradiation in human cells. Anal. Chem. 80, 2932-2938.
27. Kinoshita, S., Uzu, K., Nakano, K., and Takahashi, T. (1971) Mitomycin derivatives. 2. Derivatives of decarbamoylmitosane and decarbamoylmitosene. J. Med. Chem. 14, 109-112.
28. Palom, Y., Belcourt, M. F., Kumar, G. S., 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.
29. Tomasz, M., Lipman, R., Verdine, G. L., and Nakanishi, K. (1986) Reassignment of the guanine-binding mode of reduced mitomycin C. Biochemistry 25, 4337-4344.
30. Utzat, C. D., Clement, C. C., Ramos, L. A., Das, A., Tomasz, M., and Basu, A. K. (2005) DNA adduct of the mitomycin C metabolite 2,7-diaminomitosene is a nontoxic and nonmutagenic DNA lesion in vitro and in vivo. Chem. Res. Toxicol. 18, 213-223.
31. Champeil, E., Paz, M. M., Ladwa, S., Clement, C. C., Zatorski, A., and Tomasz, M. (2008) Synthesis of an oligodeoxyribonucleotide adduct of mitomycin C by the postoligomerization method, via a triamino mitosene. J. Am. Chem. Soc. 130, 9556-9565.
32. Suresh Kumar, G., Lipman, R., Cummings, J., and Tomasz, M. (1997) Mitomycin C-DNA adducts generated by DT-diaphorase. Revised mechanism of the reductive activation of mitomycin C. Biochemistry 36, 14128-14136.
33. Boamah, E. K., White, D. E., Talbott, K. E., Arva, N. C., Berman, D., Tomasz, M., and Bargonetti, J. (2007) Mitomycin-DNA adducts induce p53-dependent and p53-independent cell death pathways. ACS Chem. Biol. 2, 399-407.
34. Meyn, R. E., Jenkins, S. F., and Thompson, L. H. (1982) Defective removal of DNA cross-links in a repair-deficient mutant of Chinese hamster cells. Cancer Res. 42, 3106-3110.
35. Larminat, F., Cambois, G., Zdzienicka, M. Z., and Defais, M. (1998) Lack of correlation between repair of DNA interstrand cross-links and hypersensitivity of hamster cells towards mitomycin C and cisplatin. FEBS Lett. 437, 97-100.
36. Islas, A. L., Vos, J.-M., and Hanawalt, P. C. (1991) Differential introduction and repair of psoralen photoadducts to DNA in specific human genes. Cancer Res. 51, 2867-2873.
37. 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.
38. Tomasz, M., Lipman, R., Mcguinness, B. F., and Nakanishi, K. (1988) Isolation and characterization of a major adduct between mitomycin-C and DNA. J. Am. Chem. Soc. 110, 5892-5896.
39. Abbas, T., Olivier, M., Lopez, J., Houser, S., Xiao, G., Kumar, G. S., Tomasz, M., and Bargonetti, J. (2002) Differential activation of p53 by the various adducts of mitomycin C. J. Biol. Chem. 277, 40513-40519.
40. Nojima, K., Hochegger, H., Saberi, A., Fukushima, T., Kikuchi, K., Yoshimura, M., Orelli, B. J., Bishop, D. K., Hirano, S., Ohzeki, M., Ishiai, M., Yamamoto, K., Takata, M., Arakawa, H., Buerstedde, J. M., Yamazoe, M., Kawamoto, T., Araki, K., Takahashi, J. A., Hashimoto, N., Takeda, S., and Sonoda, E. (2005) Multiple repair pathways mediate tolerance to chemotherapeutic cross-linking agents in vertebrate cells. Cancer Res. 65, 11704-11711.
41. Maccubbin, A. E., Mudipalli, A., Nadadur, S. S., Ersing, N., and Gurtoo, H. L. (1997) Mutations induced in a shuttle vector plasmid exposed to monofunctionally activated mitomycin C. Environ. Mol. Mutagen. 29, 143-151.
42. Carrano, A. V., Thompson, L. H., Stretka, D. G., Minkler, J. L., Mazrimas, J. A., and Fong, S. (1979) DNA crosslinking, sister chromatid exchange and specific locus mutations. Mutat. Res. 63, 175-188.
43. Kim, S. Y., and Rockwell, S. (1995) 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.
44. Fujiwara, Y., and Tatsumi, M. (1977) Cross-link repair in human cells and its possible defect in Fanconi's anemia cells. J. Mol. Biol. 113, 635-649.