Towards a general triple helix mediated DNA recognition scheme

Abstract

This review describes new perspectives offered by the synthesis of non-natural nucleosides to overcome current limitations and extend the triplex-mediated DNA recognition scheme to any sequence. Alternate strand purine binding, direct pyrimidine recognition, and binding to the whole base-pair are described. The review highlights structural requirements to the design of modified nucleosides, as well as perturbing events such as tautomeric ambiguity and intercalation for the extended heterocyclic bases.

References

1. G. Felsenfeld, D. Davies and A. Rich, J. Am. Chem. Soc., 1957, 79, 2023.
2. H. E. Moser and P. B. Dervan, Science, 1987, 238, 645.
3. T. Le Doan, L. Perrouault, D. Praseuth, N. Habhoub, J. L. Decout, N. T. Thuong, J. Lhomme and C. Hélène, Nucleic Acids Res., 1987, 15, 7749.
4. Y.-K. Cheng and B. M. Pettitt, Prog. Biophys. Mol. Biol., 1992, 58, 225.
5. J.-S. Sun, T. Garestier and C. Hélène, Curr. Opin. Struct. Biol., 1996, 6, 327.
6. J. S. Lee, M. L. Woodsworth, L. J. P. Latimer and A. R. Morgan, Nucleic Acids Res., 1984, 12, 6603.
7. L. E. Xodo, G. Manzini, F. Quadrifoglio, G. A. van der Marel and J. H. van Boom, Nucleic Acids Res., 1991, 19, 5625.
8. A. Ono, P. O. P. Ts'o and L.-S. Kan, J. Am. Chem. Soc., 1991, 113, 4032.
9. U. von Krosigk and S. A. Benner, J. Am. Chem. Soc., 1995, 117, 5361.
10. G. Xiang, R. Bogacki and L. W. McLaughlin, Nucleic Acids Res., 1996, 24, 1963.
11. A. B. Staubli and P. B. Dervan, Nucleic Acids Res., 1994, 22, 2637.
12. J. S. Koh and P. B. Dervan, J. Am. Chem. Soc., 1992, 114, 1470.
13. P. S. Miller, P. Bhan, C. D. Cushman and T. L. Trapane, Biochemistry, 1992, 31, 6788.
14. J. Hunziker, E. S. Priestley, H. Brunar and P. B. Dervan, J. Am. Chem. Soc., 1995, 117, 3233.
15. I. Radhakrishnan and D. J. Patel, Biochemistry, 1993, 32, 11 228.
16. E. S. Priestley and P. B. Dervan, J. Am. Chem. Soc., 1995, 117, 4761.
17. T. S. Rao, R. H. Durland, D. M. Seth, M. A. Myrick, V. Bodepudi and G. R. Revankar, Biochemistry, 1995, 34, 765.
18. J. F. Milligan, S. H. Krawczyk, S. Wadwani and M. D. Matteucci, Nucleic Acids Res., 1993, 21, 327.
19. T. S. Rao, A. F. Lewis, R. S. Durland and G. R. Revankar, Tetrahedron Lett., 1993, 34, 6709.
20. V. Roig, R. Kurfurst and N. T. Thuong, Tetrahedron Lett., 1993, 34, 1601.
21. B.-W. Zhou, C. Marchand, U. Asseline, N. T. Thuong, J.-S. Sun, T. Garestier and C. Héléne, Bioconj. Chem., 1995, 6, 516.
22. S. B. Noonberg, J.-C. François, D. Praseuth, A.-L. Guieysse-Peugeot, J. Lacoste, T. Garestier and C. Hélène, Nucleic Acids Res., 1995, 23, 4042.
23. B.-W. Zhou, E. Puga, J.-S. Sun, T. Garestier and C. Héléne, J. Am. Chem. Soc., 1995, 117, 10 425.
24. R. H. Durland, T. S. Rao, V. Bodepudi, D. M. Seth, K. Jayaraman and G. R. Revankar, Nucleic Acids Res., 1995, 23, 647.
25. W. A. Greenberg and P. B. Dervan, J. Am. Chem. Soc., 1995, 117, 5016.
26. H. U. Stilz and P. B. Dervan, Biochemistry, 1993, 32, 2177.
27. T. S. Rao, M. E. Hogan and G. R. Revankar, Nucleosides Nucleotides, 1994, 13, 95.
28. L. C. Griffin, L. L. Kiessling, P. A. Beal, P. Gillespie and P. B. Dervan, J. Am. Chem. Soc., 1992, 114, 7976.
29. K. M. Koshlap, P. Gillespie, P. B. Dervan and J. Feigon, J. Am. Chem. Soc., 1993, 115, 7908.
30. C.-Y. Huang, G. Bi and P. S. Miller, Nucleic Acids Res., 1996, 24, 2606.
31. S. Sasaki, S. Nakmashima, F. Nagatsugi, Y. Tanaka, M. Hisatome and M. Maeda, Tetrahedron Lett., 1995, 36, 9521.
32. S. C. Zimmerman and P. Schmitt, J. Am. Chem. Soc., 1995, 117, 10769.
33. O. Boussif, F. Lezoualc'h, M. A. Zanta, M. D. Mergny, D. Scherman, B. Demeneix and J. P. Behr, Proc. Natl. Acad. Sci. USA, 1995, 92, 7297.
34. S. Baillet and J. P. Behr, Tetrahedron Lett., 1995, 36, 8981.
35. N. Schmid and J. P. Behr, Tetrahedron Lett., 1995, 36, 1447.
36. S. O. Doronina, S. Blanalt-Feidt and J. P. Behr, to be published..