Analysis of 1,N2-ethenoguanine and 5,6,7,9-tetrahydro-7-hydroxy-9- oxoimidazo[1,2-α]purine in DNA treated with 2-chlorooxirane by high performance liquid chromatography/electrospray mass spectrometry and comparison of amounts to other DNA adducts

Chemical Research in Toxicology

Volumn 10, Issue 2, 1997, Pages 242-247

  Müller, Michael ^a   Belas, Frank J ^a   Blair, Ian A ^a   Peter Guengerich, F ^a,b  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARCINOGEN; DNA; GUANINE DERIVATIVE; INDUSTRIAL CHEMICAL; PURINE DERIVATIVE; VINYL CHLORIDE; 1,N(2) ETHENOGUANOSINE; 1,N(2)-ETHENOGUANOSINE; 5,6,7,9 TETRAHYDRO 7 HYDROXY 9 OXOIMIDAZO(1,2 A)PURINE; 5,6,7,9-TETRAHYDRO-7-HYDROXY-9-OXOIMIDAZO(1,2-A)PURINE; CHLOROETHYLENE OXIDE; DRUG DERIVATIVE; ETHYLENE OXIDE; GUANOSINE; IMIDAZOLE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; DNA ADDUCT; DNA DETERMINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; ANIMAL; CATTLE; COMPARATIVE STUDY; DRUG EFFECT; FISH; MALE; MASS FRAGMENTOGRAPHY; SPERMATOZOON; SYNTHESIS; THYMUS;

ANIMALS; CATTLE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA; DNA ADDUCTS; ETHYLENE OXIDE; FISHES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GUANOSINE; IMIDAZOLES; MALE; PURINES; SPERMATOZOA; THYMUS GLAND;

EID: 0030614916     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx960124i     Document Type: Article

References (38)

1. Gedigk, P., Müller, R., and Bechtelsheimer, H. (1975) Morphology of liver damage among polyvinyl chloride production workers. A report on 51 cases. Ann. N.Y. Acad. Sci. 246, 278-285.
2. Buffler, P. A., Wood, S., Eifler, C., Suarez, L., and Kilian, D. J. (1979) Mortality experience of workers in a vinyl chloride monomer production plant. J. Occup. Med. 21, 195-203.
3. Nicholson, W. J., Hammond, E. C., Seidman, H., and Selikoff, I. J. (1975) Mortality experience of a cohort of vinyl chloride -polyvinyl chloride workers. Ann. N.Y. Acad. Sci. 246, 225-230.
4. Bolt, H. M. (1988) Roles of etheno-DNA adducts in tumorigenicity of olefins. Crit. Rev. Toxicol. 18, 299-309.
5. Guengerich, F. P., Min, K. S., Persmark, M., Kim, M. S., Humphreys, W. G., and Cmarik, J. L. (1994) Dihaloalkanes and polyhaloalkenes. In DNA Adducts: Identification and Significance (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartsch, H., Eds.) IARC Scientific Publications No. 125, pp 57-72, IARC Publications, Lyon.
6. Barrio, J. R., Secrist, J. A., III, and Leonard, N. J. (1972) Fluorescent adenosine and cytidine derivatives. Biochem. Biophys. Res. Commun. 46, 597-604.
7. 2,2-ethenoguanine. Synthesis and comparison of the electronic spectral properties of these linear and angular triheterocycles related to the Y bases. J. Org. Chem. 42, 3292-3296.
8. Singer, B., and Bartsch, H. (1986) The Role of Cyclic Nucleic Acid Adducts in Carcinogenesis and Mutagenesis, IARC Scientific Publications, Lyon.
9. 6-Ethenoadenosine formation, mutagenicity and murine tumor induction as indicators of the generation of an electrophilic epoxide metabolite of the closely related carcinogens ethyl carbamate (urethane) and vinyl carbamate. Carcinogenesis 11, 463-473.
10. Guengerich, F. P., Geiger, L. E., Hogy, L. L., and Wright, P. L. (1981) In vitro metabolism of acrylonitrile to 2-cyanoethylene oxide, reaction with glutathione, and irreversible binding to proteins and nucleic acids. Cancer Res. 41, 4925-4933.
11. 2-ethenoguanosine in reactions of mucochloric acid with nucleosides. Chem. Res. Toxicol. 5, 852-855.
12. 2-Ethenodeoxyguanosine as a potential marker for DNA adducts formation by trans-4-hydroxy-2-nonenal. Cancer Res. 48, 320-323.
13. Okazaki, O., Persmark, M., and Guengerich, F. P. (1993) N-Nitroso-N-methylvinylaimne: reaction of the epoxide with guanyl and adenyl moieties to yield adducts derived from both parts of the molecule. Chem. Res. Toxicol. 6, 168-173.
14. 2,3-ethenoguanine in rat tissue DNA. Carcinogenesis 11, 1287-1292.
15. 4-ethenocytosine by lipid peroxidation products and nucleic acid bases. Chem. Res. Toxicol. 8, 278-283.
16. 2-(2-oxoethyl)guanine. Chem. Res. Toxicol. 6, 635-648.
17. Walling, C., and Fredricks, P. S. (1962) Positive halogen compounds. IV. Radical reactions of chlorine and t-butyl hypochlorite with some small ring compounds. J. Am. Chem. Soc. 84, 3326-3331.
18. Guengerich, F. P., Crawford, W. M., Jr., and Watanabe, P. G. (1979) Activation of vinyl chloride to covalently bound metabolites: roles of 2-chloroethylene oxide and 2-chloroacetaldehyde. Biochemistry 18, 5177-5182.
19. Guengerich, F. P., and Raney, V. M. (1992) Formation of etheno adducts of adenosine and cytidine from 1-halooxiranes. Evidence for a mechanism involving initial reaction with the endocyclic nitrogens. J. Am. Chem. Soc. 114, 1074-1080.
20. 4]guanine, a reagent for the production of internal standards of guanyl DNA adducts. Chem. Res. Toxicol. 8, 333-337.
21. 2-alkylguanines. Biochemistry 8, 238-245.
22. Müller, M., Hutchinson, L. K., and Guengerich, F. P. (1996) Addition of deoxyribose to guanine and modified DNA bases by Lactobacillus helveticas trans-N-deoxyribosylase. Chem. Res. Toxicol. 9, 1140-1144.
23. Chaudhary, A. K., Nokubo, M., Marnett, L. J., and Blair, I. A. (1994) Analysis of the malondialdehyde-2′-deoxyguanosine adduct in rat liver DNA by gas chromatography/electron capture negative chemical ionization mass spectrometry. Biol. Mass Spectrom. 23, 457-464.
24. Ciroussel, F., Barbin, A., Eberle, G., and Bartsch, H. (1990) Investigations on the relationship between DNA ethenobase adduct levels in several organs of vinyl chloride-exposed rats and cancer susceptibility. Biochem. Pharmacol. 39, 1109-1113.
25. 4-ethenocytidine. J. Am. Chem. Soc. 98, 7408-7414.
26. Bedell, M. A., Dyroff, M. C., Doerjer, G., and Swenberg, J. A. (1986) Quantitation of etheno adducts by fluorescence detection. In The Role of Cyclic Nucleic Acid Adducts in Carcinogenesis and Mutagenesis (Singer, B., and Bartsch, H., Eds.) pp 425-436, IARC Scientific Publications, Lyon.
27. Guengerich, F. P. (1992) Roles of the vinyl chloride oxidation products 1-chlorooxirane and 2-chloroacetaldehyde in the in vitro formation of etheno adducts of nucleic acid bases. Chem. Res. Toxicol. 5, 2-5.
28. Swenberg, J. A., Fedtke, N., Ciroussel, F., Barbin, A., and Bartsch, H. (1992) Etheno adducts formed in DNA of vinyl chloride-exposed rats are highly persistent in liver. Carcinogenesis 13, 727-729.
29. Dosanjh, M. K., Chenna, A., Kim, E., Fraenkel-Conrat, H., Samson, L., and Singer, B. (1994) All four known cyclic adducts formed in DNA by the vinyl chloride metabolite chloroacetaldehyde are released by a human DNA glycosylase. Proc. Natl. Acad. Sci. U.S.A. 91, 1024-1028.
30. Barbin, A., Laib, R. J., and Bartsch, H. (1985) Lack of miscoding properties of 7-(2-oxoethyl)guanine, the major vinyl chloride - DNA adduct. Cancer Res. 45, 2440-2444.
31. 4-ethenocytosine, and 4-amino-5-(imidazol-2-yl)imidazole. Biochemistry 32, 12793-12801.
32. 2,3-etheno-deoxyguanosine, using a site-directed kinetic assay. Carcinogenesis 12, 745-747.
33. 2,3-ethenoguanine, produces G → A transitions in Escherichia coli. Proc. Natl. Sci. U.S.A. 88, 9974-9978.
34. 2,3-ethenodeoxyguanosine 5′-triphosphate. Stability of the glycosyl bond in the monomer and in poly(dG,εdG-dC). Chem. Res. Toxicol. 2, 230-233.
35. 2,3-Etheno-2′-deoxyguanosine [8,9-dihydro-9-oxo-2′-deoxy-3-β-D-ribofuranosylimidazo[2,1-b]purine]: a practical synthesis and characterization. J. Org. Chem. 58, 2552-2556.
36. Simha, D., Palejwala, V. A., and Humayun, M. Z. (1991) Mechanisms of mutagenesis by exocyclic DNA adducts. Construction and in vitro template characteristics of an oligonucleotide bearing a single site-specific ethenocytosine. Biochemistry 30, 8727-8735.
37. Moriya, M., Zhang, W., Johnson, F., and Grollman, A. P. (1994) Mutagenic potency of exocyclic DNA adducts: marked differences between Escherichia coli and simian kidney cells. Proc. Natl. Acad. Sci. U.S.A. 91, 11899-11903.
38. Leonard, N. J. (1992) Etheno-bridged nucleotides in structural diagnosis and carcinogenesis. Chemtracts: Biochemistry and Molecular Biology 3, 273-297.