Ruthenium half-sandwich complexes bound to protein kinase Pim-1

Angewandte Chemie - International Edition

Volumn 45, Issue 10, 2006, Pages 1580-1585

  Debreczeni, Judit É ^a   Bullock, Alex N ^a   Atilla, G Ekin ^b   Williams, Douglas S ^b   Bregman, Howard ^b   Knapp, Stefan ^a   Meggers, Eric ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Bioinorganic chemistry; Inhibitors; Proteins; Ruthenium

Indexed keywords

BIOINORGANIC CHEMISTRY; INHIBITORS;

ENZYMES; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; REACTION KINETICS;

RUTHENIUM COMPOUNDS;

PROTEIN KINASE INHIBITOR; PROTEIN KINASE PIM 1; RUTHENIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; PROTEIN TERTIARY STRUCTURE; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; PROTEIN KINASE INHIBITORS; PROTEIN STRUCTURE, TERTIARY; PROTO-ONCOGENE PROTEINS C-PIM-1; RUTHENIUM; STEREOISOMERISM;

EID: 33746342800     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503468     Document Type: Article

References (61)

1. a) D. J. Newman, G. M. Cragg, K. M. Snader, Nat. Prod. Rep. 2000, 17, 215-234;
2. b) J. Clardy, C. Walsh, Nature 2004, 432, 829-837.
3. a) S. L. Schreiber, Science 2000, 287, 1964-1969;
4. b) M. D. Burke, S. L. Schreiber, Angew. Chem. 2004, 116, 48-60;
5. Angew. Chem. Int. Ed. 2004, 43, 46-58.
6. For chemical space, see: C. M. Dobson, Nature 2004, 432, 824-828.
7. L. Zhang, P. J. Carroll, E. Meggers, Org. Lett. 2004, 6, 521-523.
8. H. Bregman, D. S. Williams, G. E. Atilla, F. J. Carroll, E. Meggers, J. Am. Chem. Soc. 2004, 126, 13594-13595.
9. D. S. Williams, G. E. Atilla, H. Bregman, A. Arzoumanian, P. S. Klein, E. Meggers, Angew. Chem. 2005, 117, 2020-2023;
10. Angew. Chem. Int. Ed. 2005, 44, 1984-1987.
11. Metal-based drugs: a) (Eds.: C. Orvig, M. J. Abrams), Chem. Rev. 1999, 99, 2201-2842;
12. b) Z. Guo, P. J. Sadler, Angew. Chem. 1999, 111, 1610-1630;
13. Angew. Chem. Int. Ed. 1999, 38, 1512-1531;
14. c) (Ed.: N. Farrell), Coord. Chem. Rev. 2002, 232, 1-230.
15. Metal complexes as enzyme inhibitors: A. Y. Louie, T. J. Meade, Chem. Rev. 1999, 99, 2711-2734.
16. For bioorganometallic chemistry, see: a) K. Severin, R. Bergs, W. Beck, Angew. Chem. 1998, 110, 1722-1743;
17. Angew. Chem. Int. Ed. 1998, 37, 1634-1654;
18. b) D. B. Grotjahn, Coord. Chem. Rev. 1999, 190, 1125-1141;
19. c) (Ed.: G. Jaouen), J. Organomet. Chem. 1999, 589, 1-126;
20. d) N. Metzler-Nolte, Angew. Chem. 2001, 113, 1072-1076;
21. Angew. Chem. Int. Ed. 2001, 40, 1040-1043;
22. e) R. H. Fish, G. Jaouen, Organometallics 2003, 22, 2166-2177;
23. f) R. Stodt, S. Gencaslan, I. M. Müller, W. S. Sheldrick, Eur. J. Inorg. Chem. 2003, 1873-1882;
24. g) D. Schlawe, A. Majdalani, J. Velcicky, E. Heßler, T. Wieder, A. Prokop, H.-G. Schmalz, Angew. Chem. 2004, 116, 1763-1766;
25. Angew. Chem. Int. Ed. 2004, 43, 1731-1734;
26. h) D. R. Van Staveren, N. Metzler-Nolte, Chem. Rev. 2004, 104, 5931-5985.
27. For crystal structures of metal complexes bound to proteins, see: a) K. Di Gleria, D. P. Nickerson, H. A. O. Hill, L.-L. Wong, V. Fülöp, J. Am. Chem. Soc. 1998, 120, 46-52;
28. b) W. Zhong, D. Alexeev, I. Harvey, M. Guo, D. J. B. Hunter, H. Zhu, D. J. Campopiano, P. J. Sadler, Angew. Chem. 2004, 116, 6040-6044;
29. Angew. Chem. Int. Ed. 2004, 43, 5914-5918;
30. c) I. W. McNae, K. Fishburne, A. Habtemariam, T. M. Hunter, M. Melchart, F. Wang, M. D. Walkinshaw, P. J. Sadler, Chem. Commun. 2004, 1786-1787;
31. d) M. V. Cherrier, L. Martin, C. Cavazza, L. Jacquamet, D. Lemaire, J. Gaillard, J. C. Fontecilla-Camps, J. Am. Chem. Soc. 2005, 127, 10075-10082;
32. e) S. M. Contakes, G. A. Juda, D. B. Langley, N. W. Halpern-Manners, A. P. Duff, A. R. Dunn, H. B. Gray, D. M. Dooley, J. M. Guss, H. C. Freeman, Proc. Natl. Acad. Sci. USA 2005, 102, 13451-13456.
33. For cocrystal structures of staurosporine with protein kinases, see, for example: a) L. M. Toledo, N. B. Lydon, Structure 1997, 5, 1551-1556;
34. b) A. M. Lawrie, M. E. M. Noble, P. Tunnah, N. R. Brown, L. N. Johnson, J. A. Endicott, Nat. Struct. Biol. 1997, 4, 796-801;
35. c) L. Prade, R. A. Engh, A. Girod, V. Kinzel, R. Huber, D. Bossemeyer, Structure 1997, 5, 1627-1637.
36. For protein kinase inhibitor scaffolds, see: a) C. García- Echeverría, P. Traxler, D. B. Evans, Med. Res. Rev. 2000, 20, 28-57;
37. b) A. J. Bridges, Chem. Rev. 2001, 101, 2541-2571.
38. For CDKs, see: a) M. Knockaert, P. Greengard, L. Meijer, Trends Pharmacol. Sci. 2002, 23, 417-425;
39. b) A. Huwe, R. Mazitschek, A. Giannis, Angew. Chem. 2003, 115, 2170-2187;
40. Angew. Chem. Int. Ed. 2003, 42, 2122-2138.
41. For Pim-1, see: M. Bachmann, T. Möröy, Int. J. Biochem. Cell Biol. 2005, 37, 726-730.
42. For GSK-3, see: a) H. Eldar-Finkelman, Trends Mol. Med. 2002, 8, 126-132 ;
43. b) B. W. Doble, J. R. Woodgett, J. Cell Sci. 2003, 116, 1175-1186;
44. c) R. S. Jope, G. V. W. Johnson, Trends Biochem. Sci. 2004, 29, 95-102;
45. d) P. Cohen, M. Goedert, Nat. Rev. Drug Discovery 2004, 3, 479-487.
46. For optically active organometallic compounds, see: H. Brunner, Angew. Chem. 1999, 111, 1194-1208;
47. Angew. Chem. Int. Ed. 1999, 38, 1248-1263.
48. For the synthesis of 5 and 6, see: H. Bregman, D. S. Williams, E. Meggers, Synthesis 2005, 1521-1527.
49. -1. The enantiomers do not show any significant racemization in an acetonitrile solution over a time period of 12 h.
50. S. S. Taylor, E. Radzio-Andzelm, Structure 1994, 2, 345-355.
51. For the cocrystal structure of staurosporine with Pim-1, see: M. D. Jacobs, J. Black, O. Futer, L. Swenson, B. Hare, M. Fleming, K. Saxena, J. Biol. Chem. 2005, 280, 13728-13734.
52. For attractive interactions between organic fluorine and carbonyl groups, see: a) F. Hof, D. M. Scofield, W. B. Schweizer, F. Diederich, Angew. Chem. 2004, 116, 5166-5169;
53. Angew. Chem. Int. Ed. 2004, 43, 5056-5059;
54. b) J. A. Olsen, D. W. Banner, P. Seiler, B. Wagner, T. Tschopp, U. Obst-Sander, M. Kansy, K. Müller, F. Diederich, ChemBioChem 2004, 5, 666-675.
55. For orthogonal multipolar interactions in crystal structures, see: R. Paulini, K. Müller, F. Diederich, Angew. Chem. 2005, 117, 1820-1839;
56. Angew. Chem. Int. Ed. 2005, 44, 1788-1805.
57. A. N. Bullock, J. É. Debreczeni, O. Y. Fedorov, A. Nelson, B. D. Marsden, S. Knapp, J. Med. Chem. 2005, 48, 7604-7614.
58. Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326.
59. L. C. Storoni, A. J. McCoy, R. J. Read, Acta Crystallogr. Sect. D 2004, 60, 432-438.
60. G. N. Murshudov, A. A. Vagin, E. J. Dodson, Acta. Crystallogr. Sect. D 1997, 53, 240-255.
61. D. E. McRee, J. Struct. Biol. 1999, 125, 156-165.