Synthesis and Properties of H-ras DNA Sequences Containing O6-Substituted 2'-Deoxyguanosine Residues at the First, Second, or Both Positions of Codon 12

Chemical Research in Toxicology

Volumn 1, Issue 6, 1988, Pages 391-397

  Pauly, Gary T ^a   Pei, Guo K ^a   Moschel, Robert C ^a   Powers, Marilyn ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYGUANOSINE; OLIGODEOXYRIBONUCLEOTIDE;

DNA SEQUENCE; GENE; NONHUMAN; RAT;

BASE SEQUENCE; CODON; DEOXYGUANOSINE; DEOXYRIBONUCLEOSIDES; DNA; GENES, RAS; MOLECULAR SEQUENCE DATA; OLIGODEOXYRIBONUCLEOTIDES; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0024246378     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx00006a011     Document Type: Article

References (38)

1. Sukumar, S., Notario, V., Martin-Zanca, D., and Barbacid, M. (1983) Induction of mammary carcinomas in rats by nitrosomethylurea involves malignant activation of H-ras-1 locus by mutations. Nature (London) 306, 658–661.
2. Zarbl, H., Sukumar, S., Arthur, A. V., Martin-Zanca, D., and Barbacid, M. (1985) Direct mutagenesis of Ha-ros-1 oncogenes by N-Nitroso-N-methylurea during initiation of mammary carcinogenesis in rats. Nature (London) 315, 382–385.
3. 6-alkylation of deoxyguanosine to the mutagenicity and carcinogenicity of nitrosamines and nitrosamides. Nature (London) 223, 206–207.
4. 6-methylguanine in templates for RNA polymerase. Biochim. Biophys. Acta 308, 310–316.
5. 6-methyldeoxyguanylic acid and its copolymers with deoxycytidylic acid. Biochim. Biophys. Acta 521, 770–778.
6. 6-methylguanine. Biochim. Biophys. Acta 562, 51—61.
7. 6-methylguanine into viral and plasmid genomes. Proc. Natl. Acad Sci. U.S.A. 81,13-17.
8. 6-methylguanine built into a unique site in a viral Proc. Natl. Acad. Sci. U.S.A. 81, 6271–6275.
9. 6-methylguanine in gene G of bacteriophage ϕX174. Proc. Natl. Acad. Sci. U.S.A. 82, 7173–7177.
10. 6-Methylguanine mutation and repair is nonuniform. J. Biol. Chem. 261, 9879–9885.
11. 6-methylguanine in ϕX174 replicative form DNA. Proc. Natl. Acad. Sci. U.S.A. 83, 7348–7352.
12. Hill-Perkins, M., Jones, M. D., and Karran, P. (1986) Sitespecific mutagenesis in vivo by single methylated or deaminated purine bases. Mutat. Res. 162,153-163.
13. 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.
14. Barbacid, M. (1986) Human Oncogenes. In Important Advances In Oncology (DeVita, V. T., Hillman, S., and Rosenberg, S. A., Eds.) pp 3–22, J. B. Lippincott, Co., Philadelphia.
15. Barbacid, M. (1987) ras genes. Annu. Rev. Biochem. 56, 779–827.
16. Dhar, R., Ellis, R. W., Shih, T. Y., Oroszlan, S., Shapiro, B., Maizel, J., Lowy, D., and Scolnick, E. (1982) Nucleotide sequence of the p21 transforming protein of Harvey murine sarcoma virus. Science 217, 934–937.
17. Beaucage, S. L. (1984) A simple and efficient preparation of deoxynucleoside phosphoramidites in situ. Tetrahedron Lett. 25, 375–378.
18. Barone, A. D., Tang, J.-Y., and Caruthers, M. H. (1984) In situ activation of bis-dialkylaminophosphines—a new method for synthesizing deoxyoligonucleotides on polymer supports. Nucleic Acids Res. 12, 4051-4061.
19. Moore, M. F., and Beaucage, S. L. (1985) Conceptual basis of the selective activation of bis(dialkylamino)methoxyphosphines by weak acids and its application toward the preparation of deoxynucleoside phosphoramidites in situ. J. Org. Chem. 50, 2019–2025.
20. Nielsen, J., Marugg, J. E., Taagaard, M., van Boom, J. H., and Dhal, O. (1986) Polymer-supported synthesis of deoxyoligonucleotides using in-situ prepared deoxynucleoside 2-cyanoethyl phosphoramidites. Revl. Trav. Chim. Pays-Bas 105, 33–34.
21. 6-methylguanine. J. Am. Chem. Soc. 104, 1050-1054.
22. 6Me)GCG]. Nucleic Acids Res. 11, 3393–3404.
23. 6-methylguanine opposite adenine, cytosine, guanine, and thymine. Biochemistry 23, 5686–5691.
24. 6-alkyldeoxyguanosine residues at preselected sites. Biochemistry 26, 2465–2471.
25. 6-alkylated deoxyguanosine nucleosides. Tetrahedron Lett. 23, 2253–2256.
26. 2-substituted guanosines). J. Am. Chem. Soc. 87, 3752–3759.
27. Narang, S. A., Brousseau, R., Hsiung, H. M., and Michniewicz, J. J. (1980) Chemical synthesis of deoxyoligonucleotides by the modified triester method. Methods Enzymol. 65, 610–620.
28. Borer, P. N., Dengler, B., Tinoco, I., and Uhlenbeck, O. C. (1974) Stability of ribonucleic acid double-stranded helices. J. Mol. Biol. 86, 843–853.
29. 3 double-helix formation in water and deuterium oxide. Biochemistry 20, 1409–1413.
30. 3. Biochemistry 20, 1413–1418.
31. Kierzek, R., Caruthers, M. H., Longfellow, C. E., Swinton, D., Turner, D. H., and Freier, S. M. (1986) Polymer-supported RNA synthesis and its application to test the nearest-neighbor model for duplex stability. Biochemistry 25, 7840–7846.
32. Ivanov, V. I., Minchencova, L. E., Schyolkina, A. K., and Poletayev, A. I. (1973) Different conformations of double-stranded nucleic acid in solution as revealed by circular dichroism. Biopolymers 12, 89–110.
33. Pohl, F. M. (1976) Polymorphism of a synthetic DNA in solution. Nature (London) 260, 365–366.
34. Saenger, W. (1984) Principles of Nucleic Acid Structure, Springer-Verlag, New York.
35. Topal, M. D. (1988) DNA repair, oncogenes and carcinogenesis. 691–696. Carcinogenesis
36. Briscoe, W. T., and Cotter, L.-E. (1985) DNA sequence has an effect on the extent and kinds of alkylation of DNA by a potent carcinogen. Chem.-Biol. Interact. 56, 321–331.
37. Hartley, J. A., Gibson, N. W., Kohn, K. W., and Mattes, W. B. (1986) DNA sequence selectivity of guanine-N7 alkylation by three antitumor chloroethylating agents. Cancer Res. 46, 1943–1947.
38. Mattes, W. B., Hartley, J. A., and Kohn, K. W. (1986) DNA sequence selectivity of guanine-N7 alkylation by nitrogen mustards. Nucleic Acids Res. 14, 2971–2987.