Highly cooperative DNA dialkylation by the homodimer of imidazole - pyrrole diamide - CPI conjugate with vinyl linker

Journal of the American Chemical Society

Volumn 122, Issue 8, 2000, Pages 1602-1608

  Tao, Zhi Fu ^a   Saito, Isao ^b   Sugiyama, Hiroshi ^a  

^a TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; DNA FRAGMENT; IMIDAZOLE DERIVATIVE; PYRROLE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; BASE PAIRING; DNA ALKYLATION; DNA SEQUENCE; DNA STRUCTURE; DRUG BINDING SITE; DRUG MECHANISM; GEL ELECTROPHORESIS;

EID: 0034009512     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9926212     Document Type: Article

References (37)

1. For example and applications, see: (a) Hartley, J. A. Molecular Basis of Specificity in Nucleic Acid-Drug Interaction; Pullman, B., Jortner, J., Eds.; Kluwer Academic Publishers: Netherlands, 1990; pp 513-530. (b) Nucleic Acid Targeted Drug Design; Prospt, C. L., Perun, T. J., Eds.; Dekker: New York, 1992. (c) Rajski, S. R.; Williams, R. M. Chem. Rev. 1998, 98, 2723.
2. For example and applications, see: (a) Hartley, J. A. Molecular Basis of Specificity in Nucleic Acid-Drug Interaction; Pullman, B., Jortner, J., Eds.; Kluwer Academic Publishers: Netherlands, 1990; pp 513-530. (b) Nucleic Acid Targeted Drug Design; Prospt, C. L., Perun, T. J., Eds.; Dekker: New York, 1992. (c) Rajski, S. R.; Williams, R. M. Chem. Rev. 1998, 98, 2723.
3. For example and applications, see: (a) Hartley, J. A. Molecular Basis of Specificity in Nucleic Acid-Drug Interaction; Pullman, B., Jortner, J., Eds.; Kluwer Academic Publishers: Netherlands, 1990; pp 513-530. (b) Nucleic Acid Targeted Drug Design; Prospt, C. L., Perun, T. J., Eds.; Dekker: New York, 1992. (c) Rajski, S. R.; Williams, R. M. Chem. Rev. 1998, 98, 2723.
4. (a) Advance in DNA Sequence Specific Agent; Hurley, L. H., Ed.; JAI Press: London, 1992; Vol. 1.
5. (b) Advances in DNA Sequence Specific Agents; Hurley, L. H.; Chaires, J. B., Ed.; JAI Press: London, 1996; Vol. 2.
6. (c) Advances in DNA Sequence Specific Agents; Jones, G. B., Palumbo, M., Ed.; JAI Press: London, 1998; Vol. 3.
7. (a) Wittung-Stafshede, P. Science 1998, 281, 657.
8. (b) Denison, C.; Kodadek, T. Chem. Biol. 1998, 5, R129.
9. (a) Moser, H. E.; Dervan, P. B. Science, 1987, 238, 645.
10. (b) Thoung, N. T.; Helene, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 666.
11. (c) Lukhtanov, E. A.; Mills, A. G.; Kutyavin, I. V.; Gorn, V. V.; Reed, M. W.; Meyer, R. B. Nucleic Acids Res. 1997, 25, 5077.
12. (d) Belousov, E. S.; Afonina, I. A.; Podyminogin, M A.; Gamper, H. B.; Reed, M. W.; Wydro, R. M.; Meyer, R. B. Nucleic Acids Res. 1997, 25, 3440.
13. (e) Taylor, M. J.; Dervan, P. B. Bioconjugate Chem. 1997, 8, 354.
14. (a) For recent reviews, see: Wemmer, D. E.; Dervan, P. B. Curr. Opin. Str. Biol. 1997, 7, 355. Nielsen, P. E. Chem. Eur. J. 1997, 3, 505.
15. (a) For recent reviews, see: Wemmer, D. E.; Dervan, P. B. Curr. Opin. Str. Biol. 1997, 7, 355. Nielsen, P. E. Chem. Eur. J. 1997, 3, 505.
16. (b) Lamamie de Clairac, R. P.; Geierstanger, B. H.; Mrksich, M.; Dervan, P. B. Wemmer, D. E. J. Am. Chem. Soc. 1997, 119, 7909.
17. (c) White, S.; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B. Nature 1998, 391, 468.
18. (d) Kielkopf, C. L.; Baird, E. E.; Dervan, P. B.; Rees, D. C. Nat. Struct. Biol. 1998, 5, 104.
19. (e) Yang, X.-L.; Kaenzig, C.; Lee, M.; Wang, A. H.-J. Eur. J. Biochem. 1999, 263, 646.
20. (f) Fujiwara, T.; Tao, Z.-F.; Ozeki, Y.; Saito, I.; Wang, A. H.-J.; Lee, M.; Sugiyama, H. J. Am. Chem. Soc. 1999, 121, 7706.
21. Tao, Z.-F.; Fujiwara, T.; Saito, I.; Sugiyama, H. Angew. Chem., Int. Ed. 1999, 38, 650.
22. Tao, Z.-F.; Fujiwara, T.; Saito, I.; Sugiyama, H. J. Am. Chem. Soc. 1999, 121, 4961.
23. Double-strand alkylation at homopurine sequences of DNA through triplex formation were attempted: (a) Povsic, T. J.; Strobel, S. A.; Dervan, P. B. J. Am. Chem. Soc. 1992, 114, 5934 and references therein. (b) Reed, M. W.; Wald, A.; Meyer, R. B. J. Am. Chem. Soc. 1998, 120, 9729.
24. Double-strand alkylation at homopurine sequences of DNA through triplex formation were attempted: (a) Povsic, T. J.; Strobel, S. A.; Dervan, P. B. J. Am. Chem. Soc. 1992, 114, 5934 and references therein. (b) Reed, M. W.; Wald, A.; Meyer, R. B. J. Am. Chem. Soc. 1998, 120, 9729.
25. (a) Wang, Y.; Gupta, R.; Huang, L.; Luo, W.; Lown, J. W. Anti-cancer Drug Des. 1996, 11, 15.
26. (b) Fregeau, N. L.; Wang, Y.; Pon, R. T.; Wylie, W. A.; Lown, J. W. J. Am. Chem. Soc. 1995, 117, 8917.
27. (c) Iida, H.; Lown, J. W. Recent Res. Devel. Synth. Org. Chem. 1998, 1, 17.
28. McGeary, R. P. Tetrahedron Lett. 1998, 39, 3319.
29. Wadsworth, W. S., Jr.; Emmons, W. D. J. Am. Chem. Soc. 1961, 83, 1733.
30. Nagamura, S.; Asai, A.; Kanda, Y.; Kobayashi, E.; Gomi, K.; Saito, H. Chem. Pharm. Bull. 1996, 44, 1723.
31. (a) Sugiyama, H.; Hosoda, M.; Saito, I.; Asai, A.; Saito, H. Tetrahedron Lett. 1990, 31, 7197.
32. (b) Sugiyama, H.; Ohmori, K.; Chan, K. L.; Hosoda, M.; Asai, A.; Saito, H.; Saito, I. Tetrahedron Lett. 1993, 34, 2179.
33. (c) Sugiyama, H.; Fujiwara, T.; Ura, A.; Tashiro, T.; Yamamoto, K.; Kawanishi, S.; Saito, I. Chem. Res. Toxicol. 1994, 7, 673.
34. (a) Trauger, J. W.; Baird, E. E.; Dervan, P. B. Nature 1996, 382, 559.
35. (b) Gottesfeld, J. M.; Neely, L.; Trauger, J. W.; Baird, E. E.; Dervan, P. B. Nature 1997, 387, 202.
36. (c) Dickinson, L. A.; Gulizia, R. J.; Trauger, J. W.; Baird, E. E.; Mosier, D. E.; Gottesfeld, J. M.; Dervan, P. B. Proc. Natl. Acd. Sci. U.S.A. 1998, 95, 1298.
37. Dickinson, L. A.; Trauger, J. W.; Baird, E. E.; Ghazal, P.; Dervan, P. B.; Gottesfeld, J. M. Biochemistry 1999, 38, 10801.