Dramatic increase of the DNA cleavage activity of Cu(Clip-phen) by fixing the bridging linker on the C³ position of the phenanthroline units

Abstract

The synthesis of a new ligand with two phenanthrolines bridged on their C³ carbon by a serinol is reported; Cu(3-Clip-phen) cleaves DNA more efficiently than the parent Cu(2-Clip-phen) bridged on the C² carbon.

References

1. D. S. Sigman, A. Mazumder and D. M. Perrin, Chem. Rev., 1993, 93, 2295.
2. G. Pratviel, J. Bernadou and B. Meunier, Adv. Inorg. Chem., 1998, 45, 251.
3. J. M. Veal, K. Merchant and R. L. Rill, Nucleic Acids Res., 1991, 19, 3383.
4. B. R. James and R. J. P. Williams, J. Chem. Soc., 1961, 2007.
5. M. Pitié and B. Meunier, Inorg. Chem., 1998, 37, 3486.
6. M. Pitié and B. Meunier, Bioconjugate Chem., 1998, 9, 604.
7. J. Gallagher, C. B. Chen, C. Q. Pan, D. M. Perrin, Y. Cho and D. S. Sigman, Bioconjugate Chem., 1996, 7, 413; T. B. Thederan, M. D. Kuwabara, T. A. Larsen and D. S. Sigman, J. Am. Chem. Soc., 1989, 111, 4941.
8. F. C. K. Chiu, R. T. C. Brownlee, K. Mitchell and D. R. Phillips, Bioorg. Med. Chem. Lett., 1994, 4, 2721.
9. D. Tzalis, Y. Tor, S. Failla and J. S. Siegel, Tetrahedron Lett., 1995, 36, 3489.
10. D. Tzalis and Y. Tor, Angew. Chem., Int. Ed. Engl., 1997, 36, 2666 and references therein.
11. R. P. Hertzberg and P. B. Dervan, Biochemistry, 1984, 23, 3934.
12. J. Bernadou, G. Pratviel, F. Bennis, M. Girardet and B. Meunier, Biochemistry, 1989, 28, 7268.