Synthesis of oligonucleotides containing the ethylene dibromide- derived DNA adducts s-[2-(N7-Guanyl)ethyl]glutathione, S-[2-(N2- Guanyl)ethyl]glutathione, and S-[2-(O6-Guanyl)ethyl]glutathione at a single site

Chemical Research in Toxicology

Volumn 10, Issue 10, 1997, Pages 1133-1143

  Kim, Mi Sook ^a   Guengerich, F Peter ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIBROMOETHANE; 9 FLUORENYLMETHYL CHLOROFORMATE; CARCINOGEN; DEOXYGUANOSINE DERIVATIVE; DEOXYINOSINE; GLUTATHIONE DERIVATIVE; OLIGOMER; OLIGONUCLEOTIDE; SODIUM HYDROXIDE;

ALKYLATION; ARTICLE; BACTERIOPHAGE; BASE PAIRING; CHIRALITY; DERIVATIZATION; DNA ADDUCT; GLUTATHIONE METABOLISM; MUTATION; NUCLEIC ACID BASE SUBSTITUTION; NUCLEOTIDE METABOLISM;

CARCINOGENS; DNA ADDUCTS; ETHYLENE DIBROMIDE; GLUTATHIONE; OLIGONUCLEOTIDES;

EID: 0030770458     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9701081     Document Type: Article

References (55)

1. Letz, G. A., Pond, S. M., Osterloh, J. D., Wade, R. L., and Becker, C. E. (1984) Two fatalities after acute occupational exposure to ethylene dibromide. J. Am. Med. Assoc. 252, 2428-2431.
2. 7-guanyl)ethyl]glutathione in DNA. J. Am. Chem. Soc. 110, 3284-3291.
3. 7-Guanyl)ethyl]glutathione, the major DNA adduct formed from 1,2-dibromoethane. Biochemistry 25, 2192-2198.
4. 7-guanyl)ethyl]glutathione. Cancer Res. 46, 2839-2844.
5. 7-guanyl)ethyl]-N-acetylcysteine in urine following administration of ethylene dibromide to rats. Cancer Res. 49, 5843-5851.
6. 7-guanyl)ethyl]glutathione from ethylene dibromide: effects of modulation of glutathione and glutathione S-transferase levels and the lack of a role for sulfation. Carcinogenesis 11, 419-424.
7. 7-guanyl)ethyl]glutathione as a mutagenic lesion formed from ethylene dibromide. J. Biol. Chem. 267, 6672-6679.
8. Foster, P. L., Wilkinson, W. G., Miller, J. K., Sullivan, A. D., and Barnes, W. M. (1988) An analysis of the mutagenicity of 1,2-dibromoethane to Escherichia coli: influence of DNA repair activities and metabolic pathways. Mutat. Res. 194, 171-181.
9. Ballering, L. A. P., Nivard, M. J. M., and Vogel, E. W. (1994) Mutation spectra of 1,2-dibromoethane, 1,2-dichloroethane and 1-bromo-2-chloroethane in excision repair proficient and repair deficient strains of Drosophila melanogaster. Carcinogenesis 15, 869-875.
10. Graves, R. J., Coutts, C., and Green, T. (1995) Methylene chloride-induced DNA damage: an interspecies comparison. Carcinogenesis 16, 1919-1926.
11. 7-guanyl)ethyl]glutathione. Biochemistry 30, 10513-10522.
12. 7-guanyl methyl-and thioether-substituted d(CATGCCT) derivatives with d(AGGNATC). Chem. Res. Toxicol. 6, 900-905.
13. 7-guanyl thioether derivatives of d(TGCTG*CAAG) with potential complements. Biochemistry 33, 8662-8672.
14. 1-DNA adduct. Proc. Natl. Acad. Sci. U.S.A. 93, 1535-1539.
15. Lawley, P. D., and Brookes, P. (1961) Acidic dissociation of 7:9-dialkylguanines and its possible relation to mutagenic properties of alkylating agents. Nature 192, 1081-1082.
16. Lawley, P. D., and Brookes, P. (1962) Ionization of DNA bases or base analogues as a possible explanation of mutagenesis, with special reference to 5-bromodeoxyuridine. J. Mol. Biol. 4, 216-219.
17. 6-Methylguanine is a critical determinant of 4-(methylnitrosammo)-1-(3-pyridyl)-1-butanone tumorigenesis in A/J mouse lung. Cancer Res. 51, 5557-5564.
18. 6-alkylation of deoxyguanosine to the mutagenicity and carcinogenicity of nitrosamines and nitrosamides. Nature 223, 206-207.
19. 6-methylguanine:thymine mispairs in DNA by extracts of human cells. Biochemistry 31, 7998-8008.
20. 4-alkylthymine and the mutagenic properties of these bases. Mutat. Res. 233, 81-94.
21. 6-methylguanine in a defined primed oligonucleotide when Escherichia coli DNA polymerase I is used. Proc. Natl. Acad. Sci. U.S.A. 86, 8271-8274.
22. 4-methylthymine in Escherichia coli. Biochemistry 30, 7027-7033.
23. 2-Gua, the major adduct of activated benzo[a]pyrene, when studied in an Escherichia coli plasmid using site-directed methods. Carcinogenesis 13, 1415-1425.
24. Shibutani, S., Margulis, L. A., Geacintov, N. E., and Grollman, A. P. (1993) Translesional synthesis on a DNA template containing a single stereoisomer of dG-(+)-or dG-(-)-anti-BPDE (7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene). Biochemistry 32, 7531-7541.
25. 2 position of deoxyguanosine. Chem. Res. Toxicol. 9, 630-637.
26. Einarsson, S., and Josefesson, B. (1987) Preparation of amino acid enantiomers and chiral amines using precolumn derivatization with (+)-1-(9-fluorenyl)ethyl chloroformate and reversed-phase liquid chromatography. Anal. Chem. 59, 1191-1195.
27. Humphreys, W. G., Kim, D.-H., Cmarik, J. L., Shimada, T., and Guengerich, F. P. (1990) Comparison of the DNA alkylating properties and mutagenic responses caused by a series of S-(2-haloethyl)-substituted cysteine and glutathione derivatives. Biochemistry 29, 10342-10350.
28. Carpino, L. A., and Han, G. Y. (1970) The 9-fluorenylmethoxy-carbonyl function, a new base-sensitive amino-protecting group. J. Am. Chem. Soc. 92, 5748-5749.
29. Carpino, L. A., and Han, G. Y. (1972) The 9-fluorenylmethoxy-carbonyl amino-protecting group. J. Org. Chem. 37, 3404-3409.
30. Basu, A. K., and Essigmann, J. M. (1988) Site-specifically modified oligodeoxynucleotides as probes for the structural and biological effects of DNA-damaging agents. Chem. Res. Toxicol. 1, 1-18.
31. Preston, B. D., and Loeb, L. A. (1988) Enzymatic synthesis of site-specifically modified DNA. Mutat. Res. 200, 21-35.
32. Harris, C. M., Zhou, L., Strand, E. A., and Harris, T. M. (1991) New strategy for the synthesis of oligodeoxynucleotides bearing adducts at exocyclic amino sites of purine nucleosides. J. Am. Chem. Soc. 113, 4328-4329.
33. -, human immunodeficiency virus-1 reverse transcriptase, and rat polymerase β. Biochemistry 36, 6069-6079.
34. 1-N7-guanine DNA adduct situated at a unique site. Nucleic Acids Res. 24, 2821-2828.
35. Thier, R., Pemble, S. E., Taylor, J. B., Humphreys, W. G., Persmark, M., Ketterer, B., and Guengerich, F. P. (1993) Expression of mammalian glutathione S-transferase 5-5 in Salmonella typhimurium TA1535 leads to base-pair mutations upon exposure to dihalomethanes. Proc. Natl. Acad. Sci. U.S.A. 90, 8576-8580.
36. Fink, R. M., Enns, T., Kimball, C. P., Silberstein, H. E., Bale, W. F., Maddes, S. C., and Whipple, G. H. (1944) Plasma protein metabolism-normal and associated with shock; observations using protein labeled by heavy nitrogen in lysine. J. Expt. Med. 80, 455-475.
37. Guengerich, F. P., and Broquist, H. P. (1973) Biosynthesis of slaframine, (1S,6S,8aS)-1-acetoxy-6-aminooctahydroindolizine, a parasympathomimetic alklaoid of fungal origin. II. The origin of pipecolic acid. Biochemistry 12, 4270-4274.
38. Landidi, D., and Rolla, F. (1976) A convenient synthesis of N-alkylphthalimides in a solid-liquid two-phase system in the presence of phase transfer catalysts. Synthesis 389-390.
39. Soai, K., Ookawa, A., and Kato, K. (1982) A facile one-step synthesis of N-substituted phthalimides using a catalytic amount of crown ether. Bull. Chem. Soc. Jpn. 55, 1671-1672.
40. 6-methylguanine in DNA: the crucial role of the conformation of the phosphodiester bond. Biochemistry 33, 5335-5346.
41. 6-methylguanine. J. Am. Chem. Soc. 104, 1050-1054.
42. Gaffney, B. L., and Jones, R. A. (1982) A new strategy for the protection of deoxyguanosine during oligonucleotide synthesis. Tetrahedron Lett. 22, 2257-2260.
43. 6-alkylated deoxyguanosine nucleosides. A new strategy for the protection of deoxyguanosine during oligonucleotide synthesis. Tetrahedron Lett. 23, 2253-2256.
44. 6-methylguanine opposite adenine, cytosine, guanine, and thymine. Biochemistry 23, 5686-5691.
45. 6-isopropylguanine. Biochemistry 28, 5779-5786.
46. 6-alkylguanine. Carcinogenesis 11, 811-816.
47. 4-alkylthymine. Nucleosides Nucleotides 10, 315-318.
48. 6 position of 2′-deoxyguanosine at a defined site and incorporation studies of the similarly modified 2′-deoxyguanosine-5′-triphosphate. Carcinogenesis 15, 1371-1375.
49. 6-alkyldeoxyguanosine residues at preselected sites. Biochemistry 26, 2465-2471.
50. Krieg, D. R. (1963) Specificity of chemical mutagenesis. Prog. Nucleic. Acid Res. Mol. Biol. 2, 125-168.
51. Mitsunobu, O. (1981) The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis 1-28.
52. Koole, L. H., Moody, H. M., Broedeers, N. H. L., Quaedflieg, P. J. L. M., Kuijpers, W. H. A., van Genderen, M. H. P., Coenen, J. J. M., van der Wal, S., and Buck, H. M. (1989) Synthesis of phosphate-methylated DNA fragments using 9-fluorenylmethoxycarbonyl as transient base protecting group. J. Org. Chem. 54, 1657-1664.
53. Zhou, Y., and Romano, L. J. (1993) Solid-phase synthesis of oligonucleotides containing site-specific N-(2′-deoxyguanosin-8-yl)-2-(acetylamino)fluorene adducts using 9-fluorenylmethoxy-carbonyl as the base-protecting group. Biochemistry 32, 14043-14052.
54. 6 is dependent on both the chirality of the lesion and the local sequence context. J. Biol. Chem. 268, 23427-23434.
55. 6 at the second position of N-ras codon 61. J. Biol. Chem. 270, 4990-5000.