Synthesis and spectroscopy of Ru(II)-bridged DNA hairpins

Abstract

A difunctional Ru(II) complex has been prepared which can be incorporated into synthetic oligonucleotides by means of standard solid-phase methodology and the properties of several oligonucleotide conjugates capable of forming Ru(II)-bridged hairpins have been investigated.

References

1. A. Sigel and H. Sigel, Interactions of Metal Ions with Nucleotides, Nucleic Acids, and Their Constituents, Marcel Dekker Inc., New York, 1996, vol. 32, p. 814; A. Sigel and H. Sigel, Probing of Nucleic Acids by Metal Ion Complexes of Small Molecules, Marcel Dekker Inc., New York, 1996, vol. 33, p. 678.
2. For selected examples, see: W. Bannwarth, D. Schmidt, R. L. Stallard, C. Hornung, R. Knorr and F. Müller, Helv. Chim. Acta, 1988, 71, 2085; C. J. Murphy, M. R. Arkin, Y. Jenkins, N. D. Ghatlia, S. H. Bossman, N. J. Turro and J. K. Barton, Science, 1993, 262, 1025; T. J. Meade and J. F. Kayyem, Angew. Chem., Int. Ed. Engl., 1995, 34, 352; E. Meggers, D. Kusch and B. Giese, Helv. Chim. Acta, 1997, 80, 640.
3. J. Tesler, K. A. Cruickshank, K. S. Schanze and T. L. Netzel, J. Am. Chem. Soc., 1989, 111, 7221; C. Moucheron, A. Kirsch-De Mesmaeker and J. M. Kelly, J. Photochem. Photobiol. B. Biol., 1997, 40, 91.
4. D. J. Hurley and Y. Tor, J. Am. Chem. Soc., 1998, 120, 2194.
5. F. D. Lewis, T. Wu, Y. Zhang, R. L. Letsinger, S. R. Greenfield and M. R. Wasielewski, Science, 1997, 277, 673; F. D. Lewis and R. L. Letsinger, J. Biol. Inorg. Chem., 1998, 3, 215.
6. R. L. Letsinger and T. Wu, J. Am. Chem. Soc., 1995, 117, 7323.
7. B. P. Sullivan, D. J. Salmon and T. J. Meyer, Inorg. Chem., 1978, 17, 3334.
8. K. A. Opperman, S. L. Mecklenburg and T. J. Meyer, Inorg. Chem., 1994, 33, 5295.
9. T. Brown and D. J. S. Brown, in Oligonucleotides and Analogues; A Practical Approach, ed. E. Eckstein, IRL Press, New York, 1991, pp. 1–24.
10. tert-Butyl hydroperoxide (1.0 M dichloromethane) was used as the oxidizer instead of I₂ for the completion of the synthesis. Overall yields ranged from 3–5% after purification.
11. A. Juris, V. Balzani, F. Barigelletti, S. Campanga, P. Belser and A. Von Zelewsky, Coord. Chem. Rev., 1988, 84, 85.
12. J. SantaLucia, Jr., Proc. Natl. Acad. Sci. USA, 1998, 95, 1460.
13. I. Ortmans, C. Moucheron and A. Kirsch-De Mesmaeker, Coord. Chem. Rev., 1998, 168, 233.
14. C. Sheu and C. S. Foote, J. Am. Chem. Soc., 1995, 117, 6439; S. O. Kelly and J. K. Barton, Chem. Biol., 1998, 5, 413.