Characterization of the Reaction Products of 2′-Deoxyguanosine and 1,2,3,4-Diepoxybutane after Acid Hydrolysis: Formation of Novel Guanine and Pyrimidine Adducts

Chemical Research in Toxicology

Volumn 17, Issue 4, 2004, Pages 521-528

  Zhang, Xin Yu ^a   Elfarra, Adnan A ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 HYDROXY 2 OXIRANYLETHYL) 2' DEOXYGUANOSINE; 1,3 BUTADIENE; 2 AMINO 1 (2,3,4 TRIHYDROXYBUTYL) 1,7 DIHYDRO 6H PURIN 6 ONE; 2 AMINO 1 (4 CHLORO 2,3 DIHYDROXYBUTYL) 1,7 DIHYDRO 6H PURIN 6 ONE; 2 AMINO 7 (2,3,4 TRIHYDROXYBUTYL) 1,7 DIHYDRO 6H PURIN 6 ONE; 2 AMINO 7 (3 CHLORO 2,4 DIHYDROXYBUTYL) 1,7 DIHYDRO 6H PURIN 6 ONE; 5 (3,4 DIHYDROXY 1 PYRROLIDINYL) 2,6 DIAMINO 4(3H)PYRIMIDINONE; 6 OXO 2 AMINO 9 (2 DEOXY BETA ERYTHRO PENTOFURANOSYL) 7 (2 HYDROXY 2 OXIRANYLETHYL) 6,9 DIHYDRO 1H PURINIUM; 7 HYDROXY 6 HYDROXYMETHYL 5,6,7,8 TETRAHYDROPYRIMIDO[1,2 A]PURIN 10(1H) ONE; 7,8 DIHYDROXY 1,5,6,7,8,9 HEXAHYDRO 1,3 DIAZEPINO[1,2 A]PURIN 11(11H) ONE; 7,8 DIHYDROXY 3 (2 DEOXY BETA ERYTHRO PENTOFURANOSYL) 3,5,6,7,8,9 HEXAHYDRO 1,3 DIAZEPINO[1,2 A]PURIN 11(11H) ONE; ACID; BUTADIENE DIEPOXIDE; CARCINOGEN; DEOXYGUANOSINE; GUANINE DERIVATIVE; MUTAGENIC AGENT; N (2 HYDROXY 1 OXIRANYLETHYL) 2' DEOXYGUANOSINE; NUCLEOSIDE DERIVATIVE; PURINE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DECOMPOSITION; HYDROLYSIS; METABOLITE; PH; TEMPERATURE;

BIOLOGICAL MARKERS; CARCINOGENS; DEOXYGUANOSINE; EPOXY COMPOUNDS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS;

EID: 1942486367     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx034243r     Document Type: Article

References (41)

1. Department of Health and Human Services (2000) U.S. Public Health Services, National Toxicology Program, The Ninth Report on Carcinogens, Research Triangle Park, NC.
2. 1 mice after 60 weeks of inhalation exposure. Science 227, 548-549.
3. 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.
4. Melnick, R. L., and Huff, J. (1992) 1,3-Butadiene: toxicity and carcinogenicity in laboratory animals and in humans. Rev. Environ. Contam. Toxicol. 124, 111-144.
5. Santos-Burgoa, C., Matanoski, G. M., Zeger, S., and Schwartz, L. (1992) Lymphohematopoietic cancer in styrene-butadiene polymerization workers. Am. J. Epidemiol. 136, 843-854.
6. Divine, B. J., Wendt, J. K., and Hartman, C. M. (1993) Cancer mortality among workers at a butadiene production facility. In Butadiene and Styrene: Assessment of Health Hazards (Sorsa, M., Peltonen, K., Vainio, H., and Hemminki, K., Eds.) IARC Scientific Publications No. 127, pp 345-362, IARC, Lyon.
7. Delzell, E., Sathiakumar, N., Hovinga, M., Macaluso, M., Julian, J., Larson, R., Cole, P., and Muir, D. C. F. (1996) A follow-up study of synthetic rubber workers. Toxicology 113, 182-189.
8. Macaluso, M., Larson, R., Delzell, E., Sathiakumar, N., Hovinga, M., Julian, J., Muir, D., and Cole, P. (1996) Leukemia and cumulative exposure to butadiene, styrene and benzene among workers in the synthetic rubber industry. Toxicology 113, 190-202.
9. Csanády, G. A., Guengerich, F. P., and Bond, J. A. (1992) Comparison of the biotransformation of 1,3-butadiene and its metabolite, butadiene monoepoxide, by hepatic and pulmonary tissues from humans, rats and mice. Carcinogenesis 13, 1143-1153.
10. Duescher, R. J., and Elfarra, A. A. (1992) 1,3-Butadiene oxidation by human myeloperoxidase. Role of chloride ion in catalysis of divergent pathways. J. Biol. Chem. 267, 19859-19865.
11. Duescher, R. J., and Elfarra, A. A. (1994) Human liver-microsomes are efficient catalysts of 1,3-butadiene oxidation. Evidence for major roles by cytochromes P450 2A6 and 2E1. Arch. Biochem. Biophys. 311, 342-349.
12. Krause, R. J., and Elfarra, A. A. (1997) Oxidation of butadiene monoxide to meso- and (±)-diepoxybutane by cDNA-expressed human cytochrome P450s and by mouse, rat, and human liver microsomes: evidence for preferential hydration of meso-diepoxybutane in rat and human microsomes. Arch. Biochem. Biophys. 337, 176-184.
13. Gervasi, P. G., Citti, L., Del Monte, M., Longo, V., and Benetti, D. (1985) Mutagenicity and chemical reactivity of epoxidic intermediates of the isoprene metabolism and other structurally related compounds. Mutat. Res. 156, 77-82.
14. Tice, R. R., Boucher, R., Luke, C. A., and Shelby, M. D. (1987) Comparative cytogenetic analysis of bone marrow damage induced in male B6C3F1 mice by multiple exposures to gaseous 1,3-butadiene. Environ. Mutagen. 9, 235-250.
15. Cochrane, 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. Cochrane, 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.
17. Lawley, P. D., and Brookes, P. (1967) Interstrand cross-linking of DNA by difunctional alkylating agents. J. Mol. Biol. 25, 143-160.
18. 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.
19. Zhang, X.-Y., and Elfarra, A. A. (2003) Identification and characterization of a series of nucleoside adducts formed by the reaction of 2′-deoxyguanosine and 1,2,3,4-diepoxybutane under physiological conditions. Chem. Res. Toxicol. 16, 1606-1615.
20. 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.
21. Oe, T., Kambouris, S. J., Walker, V. E., Meng, Q. X., 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.
22. Koivisto, P., Kilpeläinen, I., Rasanen, I., Adler, I.-D., Pacchierotti, F., and Peltonen, K. (1999) Butadiene diolepoxide- and diepoxybutane-derived DNA adducts at N7-guanine: a high occurrence of diolepoxide-derived adducts in mouse lung after 1,3-butadiene exposure. Carcinogenesis 20, 1253-1259.
23. 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.
24. 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.
25. Koivisto, P., and Peltonen, K. (2001) N7-guanine adducts of the epoxy metabolites of 1,3-butadiene in mice lung. Chem.-Biol. Interact. 135-136, 363-372.
26. Selzer, R. R., and Elfarra, A. A. (1999) In vitro reactions of butadiene monoxide with single- and double-stranded DNA: characterization and quantitation of several purine and pyrimidine adducts. Carcinogenesis 20, 285-292.
27. 32P-postlabeling analysis of aromatic carcinogen: DEA adducts. Cancer Res. 45, 5656-5662.
28. 32P-postlabeling. Chem. Res. Toxicol. 7, 733-739.
29. 6-oxopropenyl-2′-deoxyadenosine adduct in malondialdehyde-modified DNA using liquid chromatography/electrospray ionization tandem mass spectrometry. Carcinogenesis 17, 1167-1170.
30. Lawley, P. D., Orr, D. J., and Jarman, M. (1975) Isolation and identification of products from alkylation of nucleic acids: ethyl- and isopropyl-purines. Biochem. J. 145, 73-84.
31. Li, F., Segal, A., and Solomon, J. J. (1992) In vitro reaction of ethylene oxide with DNA and characterization of DNA adducts. Chem.-Biol. Interact. 83, 35-54.
32. Solomon, J. J., Mukai, F., Fedyk, J., and Segal, A. (1988) Reactions of propylene oxide with 2′-deoxynucleosides and in vitro with calf thymus DNA. Chem.-Biol. Interact. 67, 275-294.
33. Singer, B., and Grunberger, D. (1983) Molecular Biology of Mutagens and Carcinogens, Plenum Press, New York.
34. 5-formyl-2,5,6-triamino-4-hydroxypyrimidine as a major adduct in rat liver DNA after treatment with the carcinogens, N,N-dimethylnitrosamine or 1,2-dimethylhydrazine. Biochem. Biophys. Res. Commun. 110, 625-631.
35. 7-alkylated guanosines. Chem.-Biol. Interact. 53, 173-181.
36. Moschel, R. C., Hudgins, W. R., and Dipple, A. (1984) Substituent-induced effects on the stability of benzylated guanosines: model systems for the factors influencing the stability of carcinogen-modified nucleic acids. J. Org. Chem. 49, 363-372.
37. Kadlubar, F. F., Unruh, L. E., Beland, F. A., Straub, K. M., and Evans, F. E. (1981) Formation of DNA adducts by the carcinogen N-hydroxy-2-naphthylamine. Natl. Cancer Inst. Monogr. 58, 143-152.
38. Kriek, E., and Westra, J. G. (1980) Structural identification of the pyrimidine derivatives formed from N-(deoxyguanosin-8-yl)-2-aminofluorene in aqueous solution at alkaline pH. Carcinogenesis 1, 459-468.
39. Swenberg, J. A., Koc, H., Upton, P. B., Georguieva, N., Ranasinghe, A., Walker, V. E., and Henderson, R. (2001) Using DNA and hemoglobin adducts to improve the risk assessment of butadiene. Chem.-Biol. Interact. 135-136, 387-403.
40. Rydberg, P., Magnusson, A.-L., Zorcec, V., Granath, F., and Törnqvist, M. (1996) Adducts to N-terminal valines in hemoglobin from butadiene metabolites. Chem.-Biol. Interact. 101, 193-205.
41. Kautiainen, A., Fred, C., Rydberg, P., and Törnqvist, M. (2000) A liquid chromatography tandem mass spectrometric method for in vivo dose monitoring of diepoxybutane, a metabolite of butadiene. Rapid Commun. Mass Spectrom. 14, 1848-1853.