In situ selection of lead compounds by click chemistry: Target-guided optimization of acetylcholinesterase inhibitors

Journal of the American Chemical Society

Volumn 127, Issue 18, 2005, Pages 6686-6692

  Krasiński, Antoni ^a   Radić, Zoran ^b   Manetsch, Roman ^a   Raushel, Jessica ^a   Taylor, Palmer ^b   Sharpless, K Barry ^a   Kolb, Hartmuth C ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; DISSOCIATION; DRUG PRODUCTS; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MIXTURES; REACTION KINETICS;

ACETYLCHOLINESTERASE (ACHE); CLICK CHEMISTRY; REAGENTS; TACRINE AZIDE;

LEAD COMPOUNDS;

ACETYLENE; AZIDE; CHOLINESTERASE INHIBITOR; ISOQUINOLINE DERIVATIVE; LEAD; PHENYLTETRAHYDROISOQUINOLINE; TACRINE; TRIAZOLE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING SITE; DISSOCIATION CONSTANT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY;

ANIMALS; BINDING SITES; CHOLINESTERASE INHIBITORS; COMBINATORIAL CHEMISTRY TECHNIQUES; MICE; PHENANTHRIDINES; STEREOISOMERISM; TACRINE; TRIAZOLES;

EID: 18644384979     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja043031t     Document Type: Article

References (50)

1. Jain, A.; Huang, S. G.; Whitesides, G. M. J. Am. Chem. Soc. 1994, 116, 5057-5062.
2. Mammen, M.; Chio, S.-K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2755-2794.
3. Rideout, D. Science 1986, 233, 561-563.
4. Rideout, D.; Calogeropoulou, T.; Jaworski, J.; McCarthy, M. Biopolymers 1990, 29, 247-262.
5. Huc, I.; Lehn, J.-M. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 2106-2110.
6. Rainström, O.; Lehn, J.-M. ChemBioChem 2000, 1, 41-48.
7. Lehn, J.-M.; Eliseev, A. V. Science 2001, 291, 2331-2332.
8. Bunyapaiboonsri, T.; Ramström, O.; Lohmann, S.; Lehn, J.-M.; Peng, L.; Goeldner, M. ChemBioChem 2001, 2, 438-444.
9. Eliseev, A. V. Pharm. News 2002, 9, 207-215.
10. Ramström. O.; Lehn, J.-M. Nat. Rev. Drug Discovery 2002, 1, 26-36.
11. Otto, S. Curr. Opin. Drug Discovery Dev. 2003, 6, 509-520.
12. Erlanson, D. A.; Braisted, A. C.; Raphael, D. R.; Randal, M.; Stroud, R. M.; Gordon, E. M.; Wells, J. A. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 9367-9372.
13. Erlanson, D. A.; Lam, J. W.; Wiesmann, C.; Luong, T. N.; Simmons, R. L.; DeLano, W. L.; Choong, I. C.; Burdett, M. T.; Flanagan, W. M.; Lee, D.; Gordon, E. M.; O'Brien, T. Nat. Biotechnol. 2003, 21, 308-314.
14. Ramström, O.; Lohmann, S.; Bunyapaiboonsri, T.; Lehn, J.-M. Chem.-Eur. J. 2004, 10, 1711-1715.
15. Maly, D. J.; Choons, I. C.; Ellman, J. A. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 2419-2424.
16. Kehoe, J. W.; Maly, D. J.; Verdugo, D. E.; Armstrong, J. I.; Cook, B. N.; Ouyang, Y.-B.; Moore, K. L.; Ellman, J. A.; Bertozzi, C. R. Bioorg. Med. Chem. Lett. 2002, 12, 329-332.
17. Lewis, W. G.; Green, L. G.; Grynszpan, F.; Radić, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 1053-1057.
18. Bourne. Y.; Kolb, H. C.; Radí, Z.; Sharpless, K. B.; Taylor, P.; Marchot, P. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 1449-1454.
19. Inglese, J.; Benkovic, S. J. Tetrahedron 1991, 47, 2351-2364.
20. Boger, D. L.; Haynes, N.-E.; Kilos, P. A.; Warren, M. S.; Ramcharan, J.; Marolewski, A. E.; Benkovic, S. J. Bioorg. Med. Chem. 1997, 5, 1817-1830.
21. Greasley, S. E.; Marsilje, T. H.; Cai, H.; Baker, S.; Benkovic, S. J.; Boger, D. L.; Wilson, I. A. Biochemistry 2001, 40, 13538-13547.
22. Nguyen, R.; Hue, I. Angew. Chem., Int. Ed. 2001, 40, 1774-1776.
23. Nicolaou, K. C.; Hughes, R.; Cho, S. Y.; Winssinger, N.; Smethurst, C.; Labischinski, H.; Endermann, R. Angew. Chem., Int. Ed. 2000, 39, 3823-3828.
24. Nicolaou, K. C.; Hughes, R.; Cho, S. Y.; Winssinger, N.; Labischinski, H.; Endermann, R. Chem.-Eur. J. 2001, 7, 3824-3843.
25. Poulin-Kerstien, A. T.; Dervan, P. B. J. Am. Chem. Soc. 2003, 125, 15811-15821.
26. Manetsch, R.; Krasiński, A.; Radić, Z.; Raushel, J.; Taylor, P.; Sharpless, K. B.; Kolb, H. C. J. Am. Chem. Soc. 2004, 126, 12809-12818.
27. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 1-176.
28. Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210-216.
29. Mock W. L.; Irra, T. A.; Wepsiec, J. P.; Manimaran, T. L. J. Org. Chem. 1983, 48, 3619-3620.
30. Mock, W. L.; Irra, T. A.; Wepsiec, J. P.; Adhya, M. J. Org. Chem. 1989, 54, 5302-5308.
31. Mock, W. L. Top. Curr. Chem. 1995, 175, 1-24.
32. Du D.-M.; Carlier, P. R. Curr. Pharm. Des. 2004, 10, 3141-3156.
33. Han, Y. F.; Li. C. P.-L.; Chow, E.; Wang, H.; Pang, Y.-P.; Carlier, P. R. Bioorg. Med. Chem. 1999, 7, 2569-2575.
34. Carlier, P. R.; Han, Y. F.; Chow, E. S.-H.; Li, C. P.-L.; Wang, H.; Lieu, T. X.; Wong, H. S.; Pang, Y.-P. Bioorg. Med. Chem. 1999, 7, 351-357.
35. Pang, Y.-P.; Quiram, P.; Jelacic, T.; Hong, F.; Brimijoin, S. J. Biol. Chem. 1996, 271, 23646-23649.
36. Mocharia, V. P.; Colasson, B.; Lee, L.; Roeper, S.; Sharpless, K. B.; Wong, C.-H.; Kolb, H. C. Angew. Chem., Int. Ed. 2005, 44, 116-120.
37. Wei, J.; Buriak, J. M.; Siuzdak, G. Nature 1999, 399, 243-246.
38. Thomas, J. J.; Shen, Z.; Crowell, J. E.; Finn, M. G.; Siuzdak, G. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 4932-4937.
39. d = 23 nM.
40. Hunter, A.; Downs, C. D. J. Biol. Chem. 1945, 87, 427-446.
41. Kumar, P.; Dhawan, K. N.; Kishor, K.; Bhargava, K. P.; Satsangi, R. K. J. Heterocycl. Chem. 1982, 19, 677-679.
42. Lee, D. U.; Wiegrebe, W. Bull. Korean Chem. Soc. 1991, 12, 373-376.
43. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
44. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064.
45. Krasiński, A.; Fokin, V. V.; Sharpless, K. B. Org. Lett. 2004, 6, 1237-1240.
46. Akimova, G. S.; Chistokletov, V. N.; Petrov, A. A. Zh. Org. Khim. 1967, 3, 968-974.
47. Akimova, G. S.; Chistokletov, V. N.; Petrov, A. A. Zh. Org. Khim. 1967, 3, 2241-2247.
48. Akimova, G. S.; Chistokletov, V. N.; Petrov, A. A. Zh. Org. Khim. 1968, 4, 389-394.
49. Radić, Z.; Pickering, N. A.; Vellom. D. C.; Camp, S.; Taylor, P. Biochemistry 1993, 32, 12074-12084.
50. Marchot, P.; Ravelli, R. B. G.; Raves, M. L.; Bourne, Y.; Vellom, D. C.; Kanter, J.; Camp, S.; Sussman, J. L.; Taylor, P. Protein Sci. 1996, 5, 672-679.