Rapid and highly base selective RNA cleavage by a dinuclear Cu(II) complex

Abstract

A bis-Cu(II) complex based on a covalently linked terpyridine and bipyridine ligand system is shown to rapidly cleave bis-ribonucleotides with remarkable selectivity for adenine bases.

References

1. Reviews: B. N. Trawick, A. T. Daniher and J. K. Bashkin, Chem. Rev., 1998, 98, 939; M. Komiyama, J. Biochem., 1995, 118, 665; J. R. Morrow, Adv. Inorg. Biochem., 1994, 9, 41; M. W. Gobel, Angew. Chem., 1994, 106, 1201; Angew. Chem., Int. Ed. Engl., 1994, 33, 1141; D. S. Sigman, A. Mazumder and D. M. Perrin, Chem. Rev., 1993, 93, 2295; J. Chin, Acc. Chem. Res., 1991, 24, 145.
2. Recent examples: (a) P. Hurst, B. K. Takasaki and J. Chin, J. Am. Chem. Soc., 1996, 118, 9982; (b) M. J. Young and J. Chin, ibid., 1995, 117, 10 577; (c) B. Linkletter and J. Chin, Angew. Chem., 1995, 107, 529; Angew. Chem., Int. Ed. Engl., 1995, 34, 472; (d) W. H. Chapman, Jr. and R. Breslow, J. Am. Chem. Soc., 1995, 117, 5462; (e) M. Yashiro, A. Ishikubu and M. Komoyama, Chem. Commun., 1997, 83; (f) M. Yashiro, A. Ishikubu and M. Komiyama, J. Chem. Soc., Chem. Commun., 1995, 1793; (g) M. Komiyama, N. Takeda, M. Irisawa and M. Yashiro, in DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases, ed. B. Meunier, Kluwer Academic Publishers, Boston, 1996, p. 321; (h) J. K. Bashkin, J. Xie, A. T. Daniher, L. A. Jenkins and G. C. Yeh, ibid., p. 355; (i) R. Haner, J. Hall, D. Husken and H. E. Moser, ibid., p. 307; (j) D. Magda, R. A. Miller, M. Wright and J. Rao, ibid., p. 337; (k) J. R. Morrow and V. M. Shelton, New J. Chem., 1994, 18, 371; (l) R. Ott and R. Krämer, Angew. Chem., Int. Ed., 1998, 37, 1957.
3. C. A. Stein and J. S. Cohen, Cancer Res., 1988, 48, 2659.
4. E. Uhlmann and A. Peyman, Chem. Rev., 1990, 90, 543.
5. J. F. Milligan, M. D. Matteucci and J. C. Martin, J. Med. Chem., 1993, 36, 1923.
6. For the techniques currently available for RNA sequencing and structure mapping see: T. D. Tullus, in Bioorganic Chemistry: Nucleic Acids, ed. S. M. Hecht, Oxford University Press, New York, 1996, p. 1244.
7. S. Liu, Z. Luo and A. D. Hamilton, Angew. Chem., Int. Ed. Engl., 1997, 36, 2678.
8. S. Liu and A. D. Hamilton, Bioorg. Med. Chem. Lett., 1997, 7, 1779.
9. T. Koike and Y. Inoue, Chem. Lett., 1972, 569.
10. The background rate of hydrolysis of ApA at pH 7.5 is ca. 1.6 × 10^–10 s^–1, see Y. Matsumoto and M. Komiyama, J. Chem. Soc., Chem. Commun., 1990, 1050; K. Yoshinari and M. Komiyama, Chem. Lett., 1990, 519.