Combinatorial approach to the discovery of novel coordination complexes

Journal of the American Chemical Society

Volumn 118, Issue 37, 1996, Pages 8983-8984

  Francis, Matthew B ^a   Finney, Nathaniel S ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METAL COMPLEX;

ARTICLE; COMPLEX FORMATION; DRUG SYNTHESIS; TECHNIQUE;

EID: 0029811207     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961842u     Document Type: Article

References (25)

1. (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993.
2. (b) Comprehensive Organometallic Chemistry II; Wilkinson, G., Stone, F. G. A., Abel, E. W., Hegedus, L. S., Eds.; Pergamon: New York, 1995; Vol. 12.
3. Fluorescent Chemosensors for Ion and Molecule Recognition; Czarnik, A. W., Ed.; ACS Symposium Series 538; American Chemical Society: Washington, DC, 1992.
4. Lippard, S. J.; Berg, J. M. Principles of Bioinorganic Chemistry; University Science Books: Mill Valley, CA, 1994.
5. For recent reviews on strategies for the synthesis of small-molecule libraries, see: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (b) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123. (c) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
6. For recent reviews on strategies for the synthesis of small-molecule libraries, see: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (b) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123. (c) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
7. For recent reviews on strategies for the synthesis of small-molecule libraries, see: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (b) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123. (c) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
8. For combinatorial approaches to the study of ligand-receptor interactions, see: (a) Still, W. C. Acc. Chem. Res. 1996, 29, 155 and references therein. (b) Yu, H.; Chen, J. K.; Feng, S.; Dalgarno, D. C.; Brauer, A. W.; Schreiber, S. L. Cell 1994, 76, 933. (c) Combs, A. P.; Kapoor, T. M.; Feng, S.; Chen, J. K.; Daudé-Snow, L. F.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 287. (d) Zuckermann, R. N.; et al. J. Med. Chem. 1994, 37, 2678. (e) Wang, G. T.; Li, S.; Wideburg, N.; Krafft, G. A.; Kempf, D. J. J. Med. Chem. 1995, 38, 2995. (f) Campbell, D. A.; Bermak, J. C.; Burkoth, T. S.; Patel, D. V. J. Am. Chem. Soc. 1995, 117, 5381.
9. For combinatorial approaches to the study of ligand-receptor interactions, see: (a) Still, W. C. Acc. Chem. Res. 1996, 29, 155 and references therein. (b) Yu, H.; Chen, J. K.; Feng, S.; Dalgarno, D. C.; Brauer, A. W.; Schreiber, S. L. Cell 1994, 76, 933. (c) Combs, A. P.; Kapoor, T. M.; Feng, S.; Chen, J. K.; Daudé-Snow, L. F.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 287. (d) Zuckermann, R. N.; et al. J. Med. Chem. 1994, 37, 2678. (e) Wang, G. T.; Li, S.; Wideburg, N.; Krafft, G. A.; Kempf, D. J. J. Med. Chem. 1995, 38, 2995. (f) Campbell, D. A.; Bermak, J. C.; Burkoth, T. S.; Patel, D. V. J. Am. Chem. Soc. 1995, 117, 5381.
10. For combinatorial approaches to the study of ligand-receptor interactions, see: (a) Still, W. C. Acc. Chem. Res. 1996, 29, 155 and references therein. (b) Yu, H.; Chen, J. K.; Feng, S.; Dalgarno, D. C.; Brauer, A. W.; Schreiber, S. L. Cell 1994, 76, 933. (c) Combs, A. P.; Kapoor, T. M.; Feng, S.; Chen, J. K.; Daudé-Snow, L. F.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 287. (d) Zuckermann, R. N.; et al. J. Med. Chem. 1994, 37, 2678. (e) Wang, G. T.; Li, S.; Wideburg, N.; Krafft, G. A.; Kempf, D. J. J. Med. Chem. 1995, 38, 2995. (f) Campbell, D. A.; Bermak, J. C.; Burkoth, T. S.; Patel, D. V. J. Am. Chem. Soc. 1995, 117, 5381.
11. For combinatorial approaches to the study of ligand-receptor interactions, see: (a) Still, W. C. Acc. Chem. Res. 1996, 29, 155 and references therein. (b) Yu, H.; Chen, J. K.; Feng, S.; Dalgarno, D. C.; Brauer, A. W.; Schreiber, S. L. Cell 1994, 76, 933. (c) Combs, A. P.; Kapoor, T. M.; Feng, S.; Chen, J. K.; Daudé-Snow, L. F.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 287. (d) Zuckermann, R. N.; et al. J. Med. Chem. 1994, 37, 2678. (e) Wang, G. T.; Li, S.; Wideburg, N.; Krafft, G. A.; Kempf, D. J. J. Med. Chem. 1995, 38, 2995. (f) Campbell, D. A.; Bermak, J. C.; Burkoth, T. S.; Patel, D. V. J. Am. Chem. Soc. 1995, 117, 5381.
12. For combinatorial approaches to the study of ligand-receptor interactions, see: (a) Still, W. C. Acc. Chem. Res. 1996, 29, 155 and references therein. (b) Yu, H.; Chen, J. K.; Feng, S.; Dalgarno, D. C.; Brauer, A. W.; Schreiber, S. L. Cell 1994, 76, 933. (c) Combs, A. P.; Kapoor, T. M.; Feng, S.; Chen, J. K.; Daudé-Snow, L. F.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 287. (d) Zuckermann, R. N.; et al. J. Med. Chem. 1994, 37, 2678. (e) Wang, G. T.; Li, S.; Wideburg, N.; Krafft, G. A.; Kempf, D. J. J. Med. Chem. 1995, 38, 2995. (f) Campbell, D. A.; Bermak, J. C.; Burkoth, T. S.; Patel, D. V. J. Am. Chem. Soc. 1995, 117, 5381.
13. For combinatorial approaches to the study of ligand-receptor interactions, see: (a) Still, W. C. Acc. Chem. Res. 1996, 29, 155 and references therein. (b) Yu, H.; Chen, J. K.; Feng, S.; Dalgarno, D. C.; Brauer, A. W.; Schreiber, S. L. Cell 1994, 76, 933. (c) Combs, A. P.; Kapoor, T. M.; Feng, S.; Chen, J. K.; Daudé-Snow, L. F.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 287. (d) Zuckermann, R. N.; et al. J. Med. Chem. 1994, 37, 2678. (e) Wang, G. T.; Li, S.; Wideburg, N.; Krafft, G. A.; Kempf, D. J. J. Med. Chem. 1995, 38, 2995. (f) Campbell, D. A.; Bermak, J. C.; Burkoth, T. S.; Patel, D. V. J. Am. Chem. Soc. 1995, 117, 5381.
14. Spatially addressed synthetic libraries have been applied with success for the identification of metal-containing solid-state materials (Briceño, G.; Chang, H.; Sun, X.; Schultz, P. G.; Xiang, X.-D. Science 1995, 270, 273), Tc-binding peptides (Malin, R.; Schneider-Mergenet, J.; et al. J. Am. Chem. Soc. 1995, 117, 11821), and selective catalysts (Burgess. K.; Lim, H.-J.; Porte, A. M.; Sulikowski, G. A. Angew. Chem. Int. Ed. Engl. 1996, 35, 220).
15. Spatially addressed synthetic libraries have been applied with success for the identification of metal-containing solid-state materials (Briceño, G.; Chang, H.; Sun, X.; Schultz, P. G.; Xiang, X.-D. Science 1995, 270, 273), Tc-binding peptides (Malin, R.; Schneider-Mergenet, J.; et al. J. Am. Chem. Soc. 1995, 117, 11821), and selective catalysts (Burgess. K.; Lim, H.-J.; Porte, A. M.; Sulikowski, G. A. Angew. Chem. Int. Ed. Engl. 1996, 35, 220).
16. Spatially addressed synthetic libraries have been applied with success for the identification of metal-containing solid-state materials (Briceño, G.; Chang, H.; Sun, X.; Schultz, P. G.; Xiang, X.-D. Science 1995, 270, 273), Tc-binding peptides (Malin, R.; Schneider-Mergenet, J.; et al. J. Am. Chem. Soc. 1995, 117, 11821), and selective catalysts (Burgess. K.; Lim, H.-J.; Porte, A. M.; Sulikowski, G. A. Angew. Chem. Int. Ed. Engl. 1996, 35, 220).
17. Burger, M. T.; Still, W. C. J. Org. Chem. 1995, 60, 7382.
18. Experimental procedures for the synthesis of the library and its components are provided as supporting information.
19. Furka, A.; Sebestyen, F.; Asgedom, M.; Dibo, G. Int. J. Pept. Protein Res. 1991, 37, 487.
20. Ohlmeyer, M. H. J.; Swanson, R. N.; Dillard, L. W.; Reader, J. C.; Asouline, G.; Kobayashi, R.; Wigler, M.: Still, W. C. Proc. Natl Acad. Sci. U.S.A. 1993, 90, 10922.
21. Equilibration experiments have shown the binding of Ni(II) to be reversible under these conditions.
22. A sample of 24 000 beads, or 2.0 copies of the library, assures that 95% of the ligands are represented with 99% confidence. Burgess, K.; Liaw, A. I.; Wang, N. J. Med. Chem. 1994, 37, 2985.
23. -4 M and at a variety of higher Ni concentrations led to the identification of 16 and 17 as ligands in every case.
24. n-2). Several other hits from this binding screen have been resynthesized on solid phase for binding confirmation. Experiments to determine the association constants of these complexes are underway and will be reported separately.
25. In all cases, control experiments revealed no detectable metal ion binding to the poly(ethylene glycol) support. The structures of representative ligands for each of these metals are provided in the supporting information.