A combined parallel synthesis and screening of macrocyclic lanthanide complexes for the cleavage of phospho di- and triesters and double-stranded DNA

Journal of Combinatorial Chemistry

Volumn 1, Issue 1, 1999, Pages 96-100

  Berg, Thorsten ^a   Simeonov, Anton ^a   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; ESTER; LANTHANIDE; PHOSPHATE;

ARTICLE; CATALYSIS; CHEMISTRY; COMBINATORIAL CHEMISTRY; DRUG EFFECT; ENZYME SPECIFICITY; HYDROLYSIS; KINETICS; METABOLISM; SYNTHESIS; TIME;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; DNA; ESTERS; HYDROLYSIS; KINETICS; METALS, RARE EARTH; PHOSPHATES; SUBSTRATE SPECIFICITY; TIME FACTORS;

EID: 0032600832     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc9800125     Document Type: Article

References (45)

1. Reviews: (a) De Mesmaeker, A.; Haener, R.; Martin, P.; Moser, H. E. Acc. Chem. Res. 1995, 28, 366. (b) Sigman, D. S.; Mazumder, A.; Perrin, D. M. Chem. Rev. 1993, 2295. (c) Papavassiliou, A. G. Biochem. J. 1995, 305, 345.
2. Reviews: (a) De Mesmaeker, A.; Haener, R.; Martin, P.; Moser, H. E. Acc. Chem. Res. 1995, 28, 366. (b) Sigman, D. S.; Mazumder, A.; Perrin, D. M. Chem. Rev. 1993, 2295. (c) Papavassiliou, A. G. Biochem. J. 1995, 305, 345.
3. Reviews: (a) De Mesmaeker, A.; Haener, R.; Martin, P.; Moser, H. E. Acc. Chem. Res. 1995, 28, 366. (b) Sigman, D. S.; Mazumder, A.; Perrin, D. M. Chem. Rev. 1993, 2295. (c) Papavassiliou, A. G. Biochem. J. 1995, 305, 345.
4. (a) Linkletter, B.; Chin, J. Angew. Chem., Int. Ed. 1995, 34, 472.
5. (b) Amiji, S.; Morrow, J. R.; Lake, C. H.; Churchill, M. R. Angew. Chem., Int. Ed. 1994, 33, 773.
6. (c) Chin, K. O. A.; Morrow, J. R. Inorg. Chem. 1994, 33, 5036.
7. (d) Morrow, J. R.; Buttrey, L. A.; Shelton, V. M.; Berback, K. A. J. Am. Chem. Soc. 1992, 114, 1903.
8. (a) Ragunathan, K. G.; Schneider, H.-J. Angew. Chem., Int. Ed. 1996, 35, 1219.
9. (b) Liu, S.; Luo, Z.; Hamilton, A. D. Angew. Chem., Int. Ed. 1997, 36, 2678.
10. (a) Morrow, J. R.; Buttrey, L. A.; Berback, K. A. Inorg. Chem. 1992, 31, 16.
11. (b) Breslow, R.; Huang, D.-L. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 4080.
12. (c) Rammo, J.; Hettich, R.; Roigk, A.; Schneider, H.-J. Chem. Commun. 1996, 105.
13. (a) Molenveld, P.; Engbersen, J. F. J.; Kooijman, H.; Spek, A. L.; Reinhoudt, D. N. J. Am. Chem. Soc. 1998, 120, 6726.
14. (b) Molenveld, P.; Kapsabelis, S.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Am. Chem. Soc. 1997, 119, 2948.
15. (a) Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1993, 115, 12165.
16. (b) Chung, Y.; Akkaya, E. U.; Venkatachalam, T. K.; Czarnik, A. W. Tetrahedron Lett. 1990, 31, 5413.
17. (c) Hettich, R.; Schneider, H.-J. J. Am. Chem. Soc. 1997, 119, 5638.
18. (a) Chapman, W. H., Jr.; Breslow, R. J. Am. Chem. Soc. 1995, 117, 5462.
19. (b) De Rosch, M. A.; Trogler, W. C. Inorg. Chem. 1990, 29, 2409.
20. (a) Borman, S. Chem. Eng. News 1996, 37, 7.
21. (b) Weinberg, W. H.; Jandeleit, B.; Self, K.; Turner, H. Curr. Opin. Solid State Mater. Sci. 1998, 3, 104.
22. (c) Jandeleit, B.; Weinberg, W. H. Chem. Ind. 1998, 19, 795-798.
23. (d) Jandeleit, B.; Turner, H. W.; Uno, T.; van Beek, J. A. M.; Weinberg, W. H. Catal. Technol. In press.
24. (a) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
25. (b) Gilbertson, S. R.; Wang, X. Tetrahedron Lett. 1996, 37, 6475.
26. (c) Burgess, K.; Lim, H.-J.; Porte, A. M.; Sulikowski, G. A. Angew. Chem., Int. Ed. 1996, 35, 220.
27. (d) Shimiziu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 1997, 36, 1704.
28. (e) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 1996, 35, 1668.
29. (f) Porte, A. M.; Reibenspies, J.; Burgess, K. J. Am. Chem. Soc. 1998, 120, 9180.
30. (g) Senkan, S. M. Nature 1998, 394, 350.
31. (h) Taylor, S. J.; Morken, J. P. Science 1998, 280, 267.
32. (i) Francis, M. B.; Finney, N. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8983.
33. (k) Francis, M. B.; Jamison, T. F.; Jacobsen, E. N. Curr. Opin. Chem. Biol. 1998, 2, 422.
34. Menger, F. M.; Eliseev, A. V.; Migulin, V. A. J. Org. Chem. 1995, 60, 6666.
35. Berg, T.; Vandersteen, A.; Janda, K. D. Bioorg. Med. Chem. Lett. 1997, 8, 1221.
36. Zhao, B.; Wu, Y. J.; Tao, J. C.; Yuan, H. Z.; Mao, X. A. Polyhedron 1995,1197.
37. Larock, R. C. Comprehensive Organic Transformations; VCH: New York, 1994.
38. Kirby, A. J.; Younas, M. J. Chem. Soc. B, 1970, 1165.
39. Brown, D. M.; Usher, D. A. J. Chem. Soc. 1965, 6558.
40. Lavey, B. J.; Janda, K. D. J. Org. Chem. 1996, 61, 7633.
41. The change from a parallel to a serial format for determining kinetic parameters for the ligand-metal complexes was due to both decreased sensitivity (the path length in the plate reader is approximately 1/5 of that in a 1 mL cuvette and hence the AOD during a typical kinetic run is much lower in the plate reader) and evaporation from the 96-well plate during the course of a kinetic run combining to reduce the accuracy of the assay.
42. Baykal, U.; Akkaya, E. U. Tetrahedron Lett. 1998, 39, 5861.
43. Gao, C.; Lin, C.-H.; Lo, C.-H. L.; Mao, S.; Wirsching, P.; Lerner, R. A.; Janda, K. D. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 11777.
44. ICP-MS data for compund 4aTb: 31.2% Tb; 4cGd: 26.5% Gd; 4dDy: 35% Dy.
45. As the presence of a 1:1 complex could not completely be excluded, we based our calculations on the molecular weight of the 1:1 complexes in order to prevent too high rate enhancements due to a too high molecular weight of the metal complexes 4Ln.