Structural Characterization of the Major DNA-DNA Cross-Link of 1,2,3,4-Diepoxybutane

Chemical Research in Toxicology

Volumn 17, Issue 2, 2004, Pages 129-136

  Park, Soobong ^a   Tretyakova, Natalia ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE; 1,4 BIS(GUAN 7 YL) 2,3 BUTANEDIOL; ALKYLATING AGENT; ANTINEOPLASTIC AGENT; BUTADIENE DIEPOXIDE; BUTANEDIOL; DNA; DOUBLE STRANDED DNA; GUANINE DERIVATIVE; NUCLEIC ACID BASE; PRODRUG; TREOSULFAN; UNCLASSIFIED DRUG;

ARTICLE; CARCINOGENIC ACTIVITY; CARCINOGENICITY; CATTLE; CHROMATOGRAPHY; CHROMOSOME ABERRATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; COVALENT BOND; CYTOPATHOGENIC EFFECT; DNA ADDUCT; DNA ALKYLATION; DNA CROSS LINKING; DNA SEQUENCE; DNA STRUCTURE; GENE DELETION; GENOTOXICITY; HYDROLYSIS; MASS SPECTROMETRY; MOLECULAR STABILITY; MUTAGENICITY; NONHUMAN; POINT MUTATION; STRUCTURE ANALYSIS; SYNTHESIS; THYMUS; ULTRAVIOLET SPECTROSCOPY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA; EPOXY COMPOUNDS; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

ANIMALIA; BOS TAURUS;

EID: 1342310594     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0342058     Document Type: Article

References (39)

1. Hecht, S. S. (1999) Tobacco smoke carcinogens and lung cancer. J. Natl. Cancer Inst. 91, 1194-1210.
2. Hanks, D., and Townsley, W. E. (2000) Lymphatic and haematopoietic cancer mortality [letter]. J. Epidemiol. Community Health 54, 480.
3. Stayner, L. T., Dankovic, D. A., Smith, R. J., Gilbert, S. J., and Bailer, A. J. (2000) Human cancer risk and exposure to 1,3-butadiene-a tale of mice and men. Scand. J. Work Environ. Health 26, 322-330.
4. Malvoisin, E., and Roberfroid, M. (1982) Hepatic microsomal metabolism of 1,3-butadiene. Xenobiotica 12, 137-144.
5. Thornton-Manning, J. R., Dahl, A. R., Bechtold, W. E., Griffith, W. C., Jr., and Henderson, R. F. (1995) Disposition of butadiene monoepoxide and butadiene diepoxide in various tissues of rats and mice following a low-level inhalation exposure to 1,3-butadiene. Carcinogenesis 16, 1723-1731.
6. Henderson, R. F., Thornton-Manning, J. R., Bechtold, W. E., and Dahl, A. R. (1996) Metabolism of 1,3-butadiene: species differences. Toxicology 113, 17-22.
7. Nieusma, J. L., Claffey, D. J., Maniglier-Poulet, C., Imiolczyk, T., Ross, D., and Ruth, J. A. (1997) Stereochemical aspects of 1,3-butadiene metabolism and toxicity in rat and mouse liver microsomes and freshly isolated rat hepatocytes. Chem. Res. Toxicol. 10, 450-456.
8. Elfarra, A. A., Krause, R. J., and Selzer, R. R. (1996) Biochemistry of 1,3-butadiene metabolism and its relevance to 1,3-butadiene-induced carcinogenicity. Toxicology 113, 23-30.
9. Tretyakova, N., Lin, Y., Sangaiah, R., Upton, P. B., and Swenberg, J. A. (1997) Identification and quantitation of DNA adducts from calf thymus DNA exposed to 3,4-epoxy-1-butene. Carcinogenesis 18, 137-147.
10. Tretyakova, N. Y., Sangaiah, R., Yen, T. Y., and Swenberg, J. A. (1997) Synthesis, characterization, and in vitro quantitation of N-7-guanine adducts of diepoxybutane. Chem. Res. Toxicol. 10, 779-785.
11. Tretyakova, N., Sangaiah, R., Yen, T. Y., Gold, A., and Swenberg, J. A. (1997) Adenine adducts with diepoxybutane: isolation and analysis in exposed calf thymus DNA. Chem. Res. Toxicol. 10, 1171-1179.
12. Melnick, R. L., and Huff, J. E. (1993) 1,3-Butadiene induces cancer in experimental animals at all concentrations from 6.25 to 8000 parts per million. IARC Sci. Publ. 309-322.
13. Owen, P. E., Glaister, J. R., Gaunt, I. F., and Pullinger, D. H. (1987) Inhalation toxicity studies with 1,3-butadiene. 3. Two year toxicity/carcinogenicity study in rats. Am. Ind. Hyg. Assoc. J. 48, 407-413.
14. Melnick, R. L., Shackelford, C. C., and Huff, J. (1993) Carcinogenicity of 1,3-butadiene. Environ. Health Perspect. 100, 227-236.
15. Cochane, J. E., and Skopek, T. R. (1994) Mutagenicity of butadiene and its epoxide metabolites: I. Mutagenic potential of 1,2-epoxybutene, 1,2,3,4-diepoxybutane and 3,4-epoxy-1,2-butanediol in cultured human lymphoblasts. Carcinogenesis 15, 713-717.
16. Sasiadek, M., Norppa, H., and Sorsa, M. (1991) 1,3-Butadiene and its epoxides induce sister-chromatid exchanges in human lymphocytes in vitro. Mutat. Res 261, 117-121.
17. Recio, L., Steen, A. M., Pluta, L. J., Meyer, K. G., and Saranko, C. J. (2001) Mutational spectrum of 1,3-butadiene and metabolites 1,2-epoxybutene and 1,2,3,4-diepoxybutane to assess mutagenic mechanisms. Chem.-Biol. Interact. 135-136, 325-341.
18. Cochane, J. E., and Skopek, T. R. (1994) Mutagenicity of butadiene and its epoxide metabolites: II. Mutational spectra of butadiene, 1,2-epoxybutene and diepoxybutane at the hprt locus in splenic T cells from exposed B6C3F1 mice. Carcinogenesis 15, 719-723.
19. Meng, Q., Singh, N., Heflich, R. H., Bauer, M. J., and Walker, V. E. (2000) Comparison of the mutations at Hprt exon 3 of T-lymphocytes from B6C3F1 mice and F344 rats exposed by inhalation to 1,3-butadiene or the racemic mixture of 1,2:3,4-diepoxybutane. Mutat. Res 464, 169-184.
20. Brookes, P., and Lawley, P. D. (1961) The alkylation of guanosine and guanylic acid. J. Chem. Soc. 3923-3927.
21. Lawley, P. D., and Brookes, P. (1965) Molecular mechanism of the cytotoxic action of difunctional alkylating agents and of resistance to this action. Nature 206, 480-483.
22. Lawley, P. D., and Brookes, P. (1967) Interstrand cross-linking of DNA by difunctional alkylating agents. J. Mol. Biol. 25, 143-160.
23. Jelitto, B., Vangala, R. R., and Laib, R. J. (1989) Species differences in DNA damage by butadiene: role of diepoxybutane. Arch. Toxicol. Suppl. 13, 246-249.
24. Millard, J. T., and White, M. M. (1993) Diepoxybutane cross-links DNA at 5′-GNC sequences. Biochemistry 32, 2120-2124.
25. Burrows, C. J., and Muller, J. G. (1998) Oxidative nucleobase modifications leading to strand scission. Chem. Rev. 98, 1109-1152.
26. Maxam, A. M., and Gilbert, W. (1980) Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol. 65, 499-560.
27. Millard, J. T., and Wilkes, E. E. (2001) Diepoxybutane and diepoxyoctane interstrand cross-linking of the 5S DNA nucleosomal core particle. Biochemistry 40, 10677-10685.
28. 7 linkage of deoxyguanosine residues at the duplex sequence 5′-d(GNC). J. Am. Chem. Soc. 115, 2551-2557.
29. Rink, S. M., and Hopkins, P. B. (1995) A mechlorethamine-induced DNA interstrand cross-link bends duplex DNA. Biochemistry 34, 1439-1445.
30. Millard, J. T., Luedtke, N. W., and Spencer, R. J. (1996) The 5′-GNC preference for mustard cross-linking is preserved in a restriction fragment. Anticancer Drug Des. 11, 485-492.
31. Rajski, S. R., and Williams, R. M. (1998) DNA cross-linking agents as antitumor drugs. Chem. Rev. 98, 2723-2796.
32. Koc, H., Tretyakova, N. Y., Walker, V. E., Henderson, R. F., and Swenberg, J. A. (1999) Molecular dosimetry of N-7 guanine adduct formation in mice and rats exposed to 1,3-butadiene. Chem. Res. Toxicol. 12, 566-574.
33. Tretyakova, N. Y., Chiang, S. Y., Walker, V. E., and Swenberg, J. A. (1998) Quantitative analysis of 1,3-butadiene-induced DNA adducts in vivo and in vitro using liquid chromatography electrospray ionization tandem mass spectrometry. J. Mass Spectrom. 33, 363-376.
34. Oe, T., Kambouris, S. J., Walker, V. E., Meng, Q., Recio, L., Wherli, S., Chaudhary, A. K., and Blair, I. A. (1999) Persistence of N7-(2,3,4-trihydroxybutyl)guanine adducts in the livers of mice and rats exposed to 1,3-butadiene. Chem. Res. Toxicol. 12, 247-257.
35. Singer, B., and Grunberger, D. (1983) Molecular Biology of Mutagens and Carcinogens, Plenum Press, New York and London.
36. Carmical, J. R., Kowalczyk, A., Zou, Y., Van Houten, B., Nechev, L. V., Harris, C. M., Harris, T. M., and Lloyd, R. S. (2000) Butadiene-induced intrastrand DNA cross-links: a possible role in deletion mutagenesis. J. Biol. Chem. 275, 19482-19489.
37. Swenberg, J. A., Christova-Gueorguieva, N. I., Upton, P. B., Ranasinghe, A., Scheller, N., Wu, K. Y., Yen, T. Y., and Hayes, R. (2000) 1,3-butadiene: cancer, mutations, and adducts. Part V: Hemoglobin adducts as biomarkers of 1,3-butadiene exposure and metabolism. Res. Rep. Health Eff. Inst. 191-210.
38. Citti, L., Gervasi, P. G., Turchi, G., Bellucci, G., and Bianchini, R. (1984) The reaction of 3,4-epoxy-1-butene with deoxyguanosine and DNA in vitro: synthesis and characterization of the main adducts. Carcinogenesis 5, 47-52.
39. Masta, A., Gray, P. J., and Phillips, D. R. (1994) Molecular basis of nitrogen mustard effects on transcription processes: role of depurination. Nucleic Acids Res. 22, 3880-3886.