A new method of in situ activation for a novel class of DNA alkylating agents: Tunable metal cation complexation and activation [20]

Journal of the American Chemical Society

Volumn 122, Issue 26, 2000, Pages 6325-6326

  Boger, Dale L ^a   Wolkenberg, Scott E ^a   Boyce, Christopher W ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; METAL ION;

CATALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; DNA ALKYLATION; KINETICS; LETTER; REACTION ANALYSIS;

EID: 0034608975     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000653f     Document Type: Letter

References (25)

1. Molecular Aspects of Anticancer Drug-DNA Interactions; Neidle, S., Waring, M., Eds.; CRC: Boca Raton, 1993 and 1994; Vols. 1 and 2.
2. Johnson, D. S.; Boger, D. L. In Comprehensive Supramolecular Chemistry; Lehn, J. M., Ed.; Pergamon: Oxford, 1996; Vol. 4, Chapter 3, pp 73-176.
3. Boger, D. L.; Boyce, C. W. J. Org. Chem. 2000, 65, in press.
4. Phillips, J. P. Chem. Rev. 1956, 56, 271. Irving H.; Williams, R. J. P. J. Chem. Soc. 1953, 3192.
5. Phillips, J. P. Chem. Rev. 1956, 56, 271. Irving H.; Williams, R. J. P. J. Chem. Soc. 1953, 3192.
6. Boger, D. L.; Munk, S. A.; Zarrinmayeh, H.; Ishizaki, T.; Haught, J.; Bina, M. Tetrahedron 1991, 47, 2661.
7. 2+, lowering the apparent efficiencies of DNA alkylation. For any given application, the optimal results are going to depend on the reaction conditions (solvent, buffer, temperature, time) and the optimal catalyst from the range of metal cation catalysts can be established to tune the reactivity.
8. Gueron, M.; Weisbuch G. Biochimie 1981, 63, 821.
9. Marzilli, L. G.; Kistenmacher, T. J. Acc. Chem. Res. 1977, 10, 146.
10. Aich, P.; Dasgupta, D. Biochemistry 1995, 34, 1376. Huang, H. W.; Li, D.; Cowan, J. A. Biochimie 1995, 77, 729.
11. Aich, P.; Dasgupta, D. Biochemistry 1995, 34, 1376. Huang, H. W.; Li, D.; Cowan, J. A. Biochimie 1995, 77, 729.
12. Gao, X.; Patel, D. J. Biochemistry 1990, 29, 10940. Aich, P.; Sen, R.; Dasgupta, D. Biochemistry 1992, 31, 2988.
13. Gao, X.; Patel, D. J. Biochemistry 1990, 29, 10940. Aich, P.; Sen, R.; Dasgupta, D. Biochemistry 1992, 31, 2988.
14. Spinelli, M.; Dabrowiak, J. C. Biochemistry 1982, 21, 5862.
15. Fan, J.-Y.; Sun, D.; Yu, H.; Kerwin, S. M.; Hurley, L. H. J. Med. Chem. 1995, 38, 408.
16. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1439. Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. A. Chem. Rev. 1997, 97, 787.
17. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1439. Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. A. Chem. Rev. 1997, 97, 787.
18. Boger, D. L.; Johnson, D. S.; Yun, W. J. Am. Chem. Soc. 1994, 116, 1635. Boger, D. L.; Yun, W. J. Am. Chem. Soc. 1993, 115, 9872.
19. Boger, D. L.; Johnson, D. S.; Yun, W. J. Am. Chem. Soc. 1994, 116, 1635. Boger, D. L.; Yun, W. J. Am. Chem. Soc. 1993, 115, 9872.
20. Boger, D. L.; Hertzog, D. L.; Bollinger, B.; Johnson, D. S.; Cai, H.; Goldberg, J.; Turnbull, P. J. Am. Chem. Soc. 1997, 119, 4977. Boger, D. L.; Bollinger, B.; Hertzog, D. L.; Johnson, D. S.; Cai, H.; Mesini, P.; Garbaccio, R. M.; Jin, Q.; Kitos, P. A. J. Am. Chem. Soc. 1997, 119, 4987.
21. Boger, D. L.; Hertzog, D. L.; Bollinger, B.; Johnson, D. S.; Cai, H.; Goldberg, J.; Turnbull, P. J. Am. Chem. Soc. 1997, 119, 4977. Boger, D. L.; Bollinger, B.; Hertzog, D. L.; Johnson, D. S.; Cai, H.; Mesini, P.; Garbaccio, R. M.; Jin, Q.; Kitos, P. A. J. Am. Chem. Soc. 1997, 119, 4987.
22. Boger, D. L.; Garbaccio, R. M. Bioorg. Med. Chem. 1997, 5, 263. Boger, D. L.; Garbaccio, R. M. Acc. Chem. Res. 1999, 32, 1043.
23. Boger, D. L.; Garbaccio, R. M. Bioorg. Med. Chem. 1997, 5, 263. Boger, D. L.; Garbaccio, R. M. Acc. Chem. Res. 1999, 32, 1043.
24. Boger, D. L.; Johnson, D. S.; Yun, W.; Tarby, C. M. Bioorg. Med. Chem. 1994, 2, 115.
25. Mulay, I. L.; Roy, R.; Knox, B. E.; Suhr, N. H.; Delaney, W. E. J. Natl. Cancer Inst. 1971, 47, 1.