Measurement of the incorporation and repair of exogenous 5-hydroxymethyl-2′-deoxyuridine in human cells in culture using gas chromatography-negative chemical ionization-mass spectrometry

Chemical Research in Toxicology

Volumn 20, Issue 12, 2007, Pages 1787-1796

  Rogstad, Daniel K ^a   Darwanto, Agus ^a   Herring, Jason L ^a   Rogstad, Katherine Noyes ^a   Burdzy, Artur ^a   Hadley, Scott R ^a   Neidigh, Jonathan W ^a   Sowers, Lawrence C ^a  

^a LOMA LINDA UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 HYDROXYMETHYLDEOXYURIDINE; DNA;

ARTICLE; CONTROLLED STUDY; DERIVATIZATION; DNA DAMAGE; DNA REPAIR; DNA REPLICATION; EXCISION REPAIR; GAS CHROMATOGRAPHY; HUMAN; HUMAN CELL; MASS SPECTROMETRY; OSTEOSARCOMA CELL;

BIOLOGICAL MARKERS; CELL LINE, TUMOR; CELL SURVIVAL; DNA DAMAGE; DNA REPAIR; FORMIC ACIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; HYDROGEN PEROXIDE; HYDROLYSIS; SENSITIVITY AND SPECIFICITY; THYMIDINE; THYMINE;

EID: 38349014680     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx700221x     Document Type: Article

References (43)

1. Loeb, L. A. (1989) Endogenous carcinogenesis: molecular oncology into the twenty-first century - presidential address. Cancer Res. 49, 5489-5496.
2. Mullaart, E., Lohman, P. H., Berends, F., and Vijg, J. (1990) DNA damage metabolism and aging. Mutat. Res. 237, 189-210.
3. Teebor, G. W., Frenkel, K., and Goldstein, M. S. (1984) Ionizing radiation and tritium transmutation both cause formation of 5-hydroxymethyl- 2′-deoxyuridine in cellular DNA. Proc. Natl. Acad. Sci. U.S.A. 81, 318-321.
4. Frenkel, K., Zhong, Z. J., Wei, H. C., Karkoszka, J., Patel, U., Rashid, K., Georgescu, M., and Solomon, J. J. (1991) Quantitative high-performance liquid chromatography analysis of DNA oxidized in vitro and in vivo. Anal. Biochem. 196, 126-136.
5. Djuric, Z., Luongo, D. A., and Harper, D. A. (1991) Quantitation of 5-(hydroxymethyl)uracil in DNA by gas chromatography with mass spectral detection. Chem. Res. Toxicol. 4, 687-691.
6. Ames, B. N., Shigenaga, M. K., and Hagen, T. M. (1993) Oxidants, antioxidants, and the degenerative diseases of aging. Proc. Natl. Acad. Sci. U.S.A. 90, 7915-7922.
7. Levy, D. D., and Teebor, G. W. (1991) Site directed substitution of 5-hydroxymethyluracil for thymine in replicating φX-174am3 DNA via synthesis of 5-hydroxymethyl-2′-deoxyuridine-5′-triphosphate. Nucleic Acids Res. 19, 3337-3343.
8. Herrala, A. M., and Vilpo, J. A. (1989) Template-primer activity of 5-(hydroxymethyl)uracil-containing DNA for prokaryotic and eukaryotic DNA and RNA polymerases. Biochemistry 28, 8274-8277.
9. Mellac, S., Fazakerley, G. V., and Sowers, L. C. (1993) Structures of base pairs with 5-(hydroxymethyl)-2′-deoxyuridine in DNA determined by NMR spectroscopy. Biochemistry 32, 7779-7786.
10. Kallen, R. G., Simon, M., and Marmur, J. (1962) The occurrence of a new pyrimidine base replacing thymine in a bacteriophage DNA: 5-hydroxymethyl uracil. J. Mol. Biol. 5, 248-250.
11. Boorstein, R. J., Chiu, L. N., and Teebor, G. W. (1989) Phylogenetic evidence of a role for 5-hydroxymethyluracil-DNA glycosylase in the maintenance of 5-methylcytosine in DNA. Nucleic Acids Res. 17, 7653-7661.
12. Boorstein, R. J., Cummings, A., Jr., Marenstein, D. R., Chan, M. K., Ma, Y., Neubert, T. A., Brown, S. M., and Teebor, G. W. (2001) Definitive identification of mammalian 5-hydroxymethyluracil DNA N-glycosylase activity as SMUG1. J. Biol. Chem. 276, 41991-41997.
13. Baker, D., Liu, P., Burdzy, A., and Sowers, L. C. (2002) Characterization of the substrate specificity of a human 5-hydroxymethyluracil glycosylase activity. Chem. Res. Toxicol. 15, 33-39.
14. Zhang, Q. M., Yonekura, S. I., Takao, M., Yasui, A., Sugiyama, H., and Yonei, S. (2005) DNA glycosylase activities for thymine residues oxidized in the methyl group are functions of the hNEIL1 and hNTH1 enzymes in human cells. DNA Repair 4, 71-79.
15. Rogstad, D. K., Liu, P., Burdzy, A., Lin, S. S., and Sowers, L. C. (2002) Endogenous DNA lesions can inhibit the binding of the AP-1 (c-Jun) transcription factor. Biochemistry 41, 8093-8102.
16. Ivarie, R. (1987) Thymine methyls and DNA-protein interactions. Nucleic Acids Res. 15, 9975-9983.
17. Kaufman, E. R. (1986) Biochemical analysis of toxic effects of 5-hydroxymethyl-2′-deoxyuridine in mammalian cells. Somat. Cell Mol. Genet. 12, 501-512.
18. Boorstein, R. J., Chiu, L. N., and Teebor, G. W. (1992) A mammalian cell line deficient in activity of the DNA repair enzyme 5-hydroxymethyluracil-DNA glycosylase is resistant to the toxic effects of the thymidine analog 5-hydroxymethyl-2′-deoxyuridine. Mol. Cell Biol. 12, 5536-5540.
19. Mi, L. J., Chaung, W., Horowitz, R., Teebor, G. W., and Boorstein, R. J. (2001) Excessive base excision repair of 5-hydroxymethyluracil from DNA induces apoptosis in Chinese hamster V79 cells containing mutant p53. Carcinogenesis 22, 179-186.
20. Horton, J. K., Joyce-Gray, D. F., Pachkowski, B. F., Swenberg, J. A., and Wilson, S. H. (2003) Hypersensitivity of DNA polymerase β null mouse fibroblasts reflects accumulation of cytotoxic repair intermediates from site-specific alkyl DNA lesions. DNA Repair 2, 27-48.
21. Horton, J. K., Stefanick, D. F., Naron, J. M., Kedar, P. S., and Wilson, S. H. (2005) Poly(ADP-ribose) polymerase activity prevents signaling pathways for cell cycle arrest after DNA methylating agent exposure. J. Biol. Chem. 280, 15773-15785.
22. Braithwaite, E. K., Kedar, P. S., Lan, L., Polosina, Y. Y., Asagoshi, K., Poltoratsky, V. P., Horton, J. K., Miller, H., Teebor, G. W., Yasui, A., and Wilson, S. H. (2005) DNA polymerase λ protects mouse fibroblasts against oxidative DNA damage and is recruited to sites of DNA damage/repair. J. Biol. Chem. 280, 31641-31647.
23. Meldrum, J. B., Gupta, V. S., Lowes, N. R., and Paterson, A. R. (1985) Toxicologic and antitumor studies on 5-hydroxymethyldeoxyuridine. Toxicol. Appl. Pharmacol. 79, 423-435.
24. 14C]-derivative with normal and leukemic human hematopoietic cells. Acta Chem. Scand., Ser. B 39, 477-484.
25. Kahilainen, L., Bergstrom, D., Kangas, L., and Vilpo, J. A. (1986) In vitro and in vivo studies of a promising antileukemic thymidine analogue, 5-hydroxymethyl-2′-deoxyuridine. Biochem. Pharmacol. 35, 4211-4215.
26. Vilpo, J. A., Suvanto, E., and Kangas, L. (1987) Antileukemic activity against L1210 leukemia, pharmacokinetics and hematological side effects of 5-hydroxymethyl-2′-deoxyuridine. Leuk. Res. 11, 877-880.
27. Giese, R. W. (1997) Detection of DNA adducts by electron capture mass spectrometry. Chem. Res. Toxicol. 10, 255-270.
28. Saha, M., Kresbach, G. M., Giese, R. W., Annan, R. S., and Vouros, P. (1989) Preparation and mass spectral characterization of pentafluorobenzyl derivatives of alkyl and hydroxyalkyl-nucleobase DNA adducts. Biomed. Environ. Mass Spectrom. 18, 958-972.
29. Annan, R. S., Kresbach, G. M., Giese, R. W., and Vouros, P. (1989) Trace detection of modified DNA bases via moving-belt liquid chromatography-mass spectrometry using electrophoric derivatization and negative chemical ionization. J. Chromatogr. 465, 285-296.
30. Kresbach, G. M., Itani, M., Saha, M., Rogers, E. J., Vouros, P., and Giese, R. W. (1989) Ester and related derivatives of ring N- pentafluorobenzylated 5-hydroxymethyluracil. Hydrolytic stability, mass spectral properties, and trace detection by gas chromatography-electron-capture detection, gas chromatography-electron-capture negative ion mass spectrometry, and moving-belt liquid chromatography-electron-capture negative ion mass spectrometry. J. Chromatogr. 476, 423-438.
31. Abdel-Baky, S., and Giese, R. W. (1991) Gas chromatography/electron capture negative-ion mass spectrometry at the zeptomole level. Anal. Chem. 63, 2986-2989.
32. Teixeira, A. J., Gommers-Ampt, J. H., Van de Werken, G., Westra, J. G., Stavenuiter, J. F., and de Jong, A. P. (1993) Method for the analysis of oxidized nucleosides by gas chromatography/mass spectrometry. Anal. Biochem. 214, 474-483.
33. Chen, H. J., Wu, C. F., and Huang, J. L. (2005) Measurement of urinary excretion of 5-hydroxymethyluracil in human by GC/NICI/MS: correlation with cigarette smoking, urinary TBARS and etheno DNA adduct. Toxicol. Lett. 155, 403-410.
34. LaFrancois, C. J., Yu, K., and Sowers, L. C. (1998) Quantification of 5-(Hydroxymethyl)uracil in DNA by gas chromatography/mass spectrometry: problems and solutions. Chem. Res. Toxicol. 11, 786-793.
35. LaFrancois, C. J., Fujimoto, J., and Sowers, L. C. (1998) Synthesis and characterization of isotopically enriched pyrimidine deoxynucleoside oxidation damage products. Chem. Res. Toxicol. 11, 75-83.
36. Cline, R. E., Fink, R. M., and Fink, K. (1959) Synthesis of 5-substituted pyrimidines via formaldehyde addition. J. Am. Chem. Soc. 81, 2521-2527.
37. Schreiber, E., Matthias, P., Muller, M. M., and Schaffner, W. (1989) Rapid detection of octamer binding proteins with 'mini-extracts', prepared from a small number of cells. Nucleic Acids Res. 17, 6419.
38. Jiang, Q., Blount, B. C., and Ames, B. N. (2003) 5-Chlorouracil, a marker of DNA damage from hypochlorous acid during inflammation. J. Biol. Chem. 278, 32834-32840.
39. Klecker, R. W., Katki, A. G., and Collins, J. M. (1994) Toxicity, metabolism, DNA incorporation with lack of repair, and lactate production for 1-(2′-fluoro-2′-deoxy-β-D-arabinofuranosyl)-5-iodouracil in U-937 and MOLT-4 cells. Mol. Pharmacol. 46, 1204-1209.
40. Rusmintratip, V., Riggs, A. D., and Sowers, L. C. (2000) Examination of the DNA substrate selectivity of DNA cytosine methyltransferases using mass tagging. Nucleic Acids Res. 28, 3594-3599.
41. Mellac, S., Fazakerley, G. V., and Sowers, L. C. (1994) Structures of oligonucleotides containing 5-(methoxymethyl)-2′-deoxyuridine determined by NMR spectroscopy. J. Biomol. Struct. Dyn. 11, 1017-1033.
42. Rusmintratip, V., and Sowers, L. C. (2000) An unexpectedly high excision capacity for mispaired 5-hydroxymethyluracil in human cell extracts. Proc. Natl. Acad. Sci. U.S.A. 97, 14183-14187.
43. Liu, P., Burdzy, A., and Sowers, L. C. (2003) Repair of the mutagenic DNA oxidation product, 5-formyluracil. DNA Repair 2, 199-210.