Regioselective synthesis of 1,N2-Etheno-2′-deoxyguanosine and its generation in oligomeric DNA

Chemical Research in Toxicology

Volumn 16, Issue 6, 2003, Pages 708-714

  Huang, Yanhe ^a   Torres, M Cecilia ^a   Iden, Charles R ^a   Johnson, Francis ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,N2 ETHENO 2' DEOXYGUANOSINE; ALKANE DERIVATIVE; ALKYLATING AGENT; CHLOROACETALDEHYDE; CHLOROETHYLENE OXIDE; DEOXYADENOSINE DERIVATIVE; DEOXYCYTIDINE; DEOXYGUANOSINE DERIVATIVE; DNA; DNA BASE; ETHYLENE OXIDE DERIVATIVE; FATTY ACID DERIVATIVE; OLIGOMER; PERIODATE SODIUM; PHOSPHORAMIDIC ACID DERIVATIVE; PROPANE; UNCLASSIFIED DRUG; VINYL CHLORIDE;

ARTICLE; DEHYDRATION; DNA ADDUCT; DNA ALKYLATION; LABORATORY AUTOMATION; OXIDATION; PHYSICAL CHEMISTRY; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037974281     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx025659s     Document Type: Article

References (27)

1. U.S. Department of Health and Human Services, Public Health Service, National Toxicology Program (2002) Tenth Report on Carcinogens: Vinyl Chloride, Government Printing Office, Washington, DC.
2. Gross, H., and Freiberg, J. (1969) α-Haloethers XLI. Existence of chloroethylene oxide. J. Prakt. Chem. 311, 506-510.
3. Barbin, A., Bresil, H., Croisy, A., Jacquignon, P., Malaveille, C., Montesano, R., and Bartsch, H. (1975) Liver-microsome-mediated formation of alkylating agents from vinyl bromide and vinyl chloride. Biochem. Biophys. Res. Commun. 67, 596-603.
4. Laib, R. J. (1986) The role of cyclic base adducts in vinyl chloride-induced carcinogenesis: Studies on nucleic acid alkylation in vivo. In The Role of Cyclic Nucleic Acid Adducts in Carcinogenesis and Mutagenesis, IARC Scientific Publications: No. 70 (Singer, B., and Bartsch, H., Eds.) pp 101-108, Oxford University Press, Oxford.
5. Malaveille, C., Bartsch, H., Barbin, A., Camus, A. M., Metesano, R., Croisy, A., and Jacquignon, P. (1975) Mutagenicity of vinyl chloride, chloroethylene oxide, chloroacetaldehyde, and chloroethanol. Biochem. Biophys. Res. Commun. 63, 363-370.
6. 2,3-ethenodeoxyguanosine in rat tissue DNA. Carcinogenesis 11, 1287-1292.
7. Jones, B. K., and Hathaway, D. E. (1978) The biological fate of vinylidene chloride in rats. Chem.-Biol. Interact. 20, 27-41.
8. 4-ethenocytidine moieties in RNA by vinyl chloride metabolites in vitro and in vivo. Arch. Toxicol. 39, 235-237.
9. 6-etheno-adenosine. Toxicology 8, 185-188.
10. Lee, S. H., Oe, T., and Blair, I. A. (2001) Vitamin C-induced decomposition of lipid hydroperoxides to endogenous genotoxins. Science 292, 2083-2086.
11. 6-etheno-2′-deoxyadenosine adduct by lipid hydroperoxide-mediated generation of 4-oxo-2-nonenal. Chem. Res. Toxicol. 13, 846-852.
12. 2-etheno-2′-deoxyguanosine adduct formation. Chem. Res. Toxicol. 13, 601-609.
13. Lee, S. H., Rindgen, D., Bible, R. H., Jr., Hajdu, E., and Blair, I. A. (2000) Characterization of 2′-deoxyadenosine adducts derived from 4-oxo-2-nonenal, a novel product of lipid peroxidation. Chem. Res. Toxicol. 13, 565-574.
14. 2-ethenodeoxyguanosine as a potential marker for DNA adduct formation by trans-4-hydroxy-2-nonenal. Cancer Res. 48, 320-323.
15. 2-ethenoguanine, 5,6,7,9-tetrahydro-9-oxoimidazo[1,2-α]purine, and 5,6,7,9-tetrahydro-7-hydroxy-9-oxoimidazo[1,2-α]purine. Biochemistry 37, 5184-5193.
16. 2-ethenoguanine in Chinese hamster ovary cell chromosomal DNA. Chem. Res. Toxicol. 12, 501-507.
17. 4-ethano, and 3-(2-hydroxyethyl) derivatives of 2′-deoxycytidine and their incorporation into oligomeric DNA. Chem. Res. Toxicol. 8, 148-156.
18. Moriya, M., Zhang, W., Johnson, F., and Grollman, A. P. (1994) Mutagenic potency ofexocyclic DNA adducts: Marked differences between Escherichia coli and simian kidney cells. Proc. Natl. Acad. Sci. U.S.A. 91, 11899-11903.
19. Nechev, L. V., Harris, C. M., and Harris, T. M. (2000) Synthesis of nucleosides and oligonucleotides containing adducts of acrolein and vinyl chloride. Chem. Res. Toxicol. 13, 421-429.
20. -, human immunodeficiency virus-1 reverse transcriptase, and rat polymerase β. Biochemistry 36, 6069-6079.
21. 2 position of deoxyguanosine. Chem. Res. Toxicol. 9, 630-637.
22. 2-(2-oxoethyl)guanine. Chem. Res. Toxicol. 6, 635-648.
23. Khullar, S., Varaprasad, C. V., and Johnson, F. J. (1999) Postsynthetic generation of a major acrolein adduct of 2′-deoxyguanosine in oligomeric DNA. J. Med. Chem. 42, 947-950.
24. 2-Ethenodeoxyguanosine: properties and formation in chloroacetaldehyde-treated polynucleotides and DNA. Chem. Res. Toxicol. 5, 634-638.
25. Shibutani, S., Bodepudi, V., Johnson, F., and Grollman, A. P. (1993) Translesional synthesis on DNA templates containing 8-oxo-7,8-dihydrodeoxyadenosine. Biochemistry 32, 4615-4621.
26. Iriuchijima, S., and Kojima, N. (1982) Asymmetric hydrolysis of esters by biochemical methods. Part III. Asymmetric hydrolysis of (±)-1,2-diacetoxy-3-chloropropane and its related compounds with lipase. Synthesis of optically pure (S)-propranolol. Agric. Biol. Chem. 46, 1153-1157.
27. Huang, Y., and Johnson, F. (2002) Regioselective 1-Alkylation of 2′-deoxyguanosine. Nucleosides, Nucleotides, Nucleic Acids 21, 435-447.