Design, synthesis, and evaluation of small molecule Hsp90 probes

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 8, 2011, Pages 2603-2614

  Taldone, Tony ^a   Zatorska, Danuta ^a   Patel, Pallav D ^a   Zong, Hongliang ^b   Rodina, Anna ^a   Ahn, James H ^a   Moulick, Kamalika ^a   Guzman, Monica L ^b   Chiosis, Gabriela ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b WEILL CORNELL MEDICAL COLLEGE   (United States)

Author keywords

Cancer; Docking; Heat shock protein 90; NVP AUY922; PU H71; SNX 2112

Indexed keywords

5 (2,4 DIHYDROXY 5 ISOPROPYLPHENYL) 4 (4 MORPHOLINOMETHYLPHENYL) 3 ISOXAZOLECARBOXYLIC ACID ETHYLAMIDE; HEAT SHOCK PROTEIN 90 INHIBITOR; INDAZOL 4 ONE DERIVATIVE; ISOXAZOLE DERIVATIVE; MOLECULAR MARKER; PU H 71; SNX 2112; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; BINDING COMPETITION; BREAST CANCER; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; ENZYME INHIBITOR COMPLEX; LEUKEMIA CELL LINE; MOLECULAR DOCKING; MOLECULAR PROBE;

ANTINEOPLASTIC AGENTS; BINDING, COMPETITIVE; DRUG DESIGN; HSP90 HEAT-SHOCK PROTEINS; HUMANS; MOLECULAR PROBES;

EID: 79954414696     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.03.013     Document Type: Article

References (45)

1. B. Panaretou, C. Prodromou, S.M. Roe, R. O'Brien, J.E. Ladbury, P.W. Piper, and L.H. Pearl EMBO 17 1998 4829
2. W.M.J. Obermann, H. Sondermann, A.A. Russo, N.P. Pavletich, and F.U. Hartl J. Cell Biol. 143 1998 901
3. L. Whitesell, and S.L. Lindquist Nat. Rev. Cancer 5 2005 761
4. T. Taldone, W. Sun, and G. Chiosis Bioorg. Med. Chem. 17 2009 2225
5. Y. Janin Drug Discovery Today 15 2010 342
6. D.B. Solit, F.F. Zheng, M. Drobnjak, P.N. Munster, B. Higgins, D. Verbel, G. Heller, W. Tong, C. Cardon-Cardo, D.B. Agus, H.I. Scher, and N. Rosen Clin. Cancer Res. 8 2002 986
7. P.A. Brough, W. Aherne, X. Barril, J. Borgognoni, K. Boxall, J.E. Cansfield, K.-M.J. Cheung, I. Collins, N.G.M. Davies, M.J. Drysdale, B. Dymock, S.A. Eccles, H. Finch, A. Fink, A. Hayes, R. Howes, R.E. Hubbard, K. James, A.M. Jordan, A. Lockie, V. Martins, A. Massey, T.P. Matthews, E. McDonald, C.J. Northfield, L.H. Pearl, C. Prodromou, S. Ray, F.I. Raynaud, S.D. Roughley, S.Y. Sharp, A. Surgenor, D.L. Walmsley, P. Webb, M. Wood, P. Workman, and L. Wright J. Med. Chem. 51 2008 196
8. S. Chandarlapaty, A. Sawai, Q. Ye, A. Scott, M. Silinski, K. Huang, P. Fadden, J. Partdrige, S. Hall, P. Steed, L. Norton, N. Rosen, and D.B. Solit Clin. Cancer Res. 14 2008 240
9. E. Caldas-Lopes, L. Cerchietti, J.H. Ahn, C.C. Clement, A.I. Robles, A. Rodina, K. Moulick, T. Taldone, A. Gozman, Y. Guo, N. Wu, E. de Stanchina, J. White, S.S. Gross, Y. Ma, L. Varticovski, A. Melnick, and G. Chiosis Proc. Natl Acad. Sci. USA 106 2009 8368
10. C.P. Carden, D. Sarker, S. Postel-Vinay, T.A. Yap, G. Attard, U. Banerji, M.D. Garrett, G.V. Thomas, P. Workman, S.B. Kaye, and J.S. de Bono Drug Discovery Today 15 2010 88
11. L. Whitesell, E.G. Mimnaugh, B. De Costa, C.E. Myers, and L.M. Neckers Proc. Natl Acad. Sci. USA 91 1994 8324
12. H. He, D. Zatorska, J. Kim, J. Aguirre, L. Llauger, Y. She, N. Wu, R.M. Immormino, D.T. Gewirth, and G. Chiosis J. Med. Chem. 49 2006 381
13. K.H. Huang, J.M. Veal, R.P. Fadden, J.W. Rice, J. Eaves, J.-P. Strachan, A.F. Barabasz, B.E. Foley, T.E. Barta, W. Ma, M.A. Silinski, M. Hu, J.M. Partridge, A. Scott, L.G. DuBois, T. Freed, P.M. Steed, A.J. Ommen, E.D. Smith, P.F. Hughes, A.R. Woodward, G.J. Hanson, W.S. McCall, C.J. Markworth, L. Hinkley, M. Jenks, L. Geng, M. Lewis, J. Otto, B. Pronk, K. Verleysen, and S.E. Hall J. Med. Chem. 52 2009 4288
14. R.C. Clevenger, J.M. Raibel, A.M. Peck, and B.S.J. Blagg J. Org. Chem. 69 2004 4375
15. Y. Du, K. Moulick, A. Rodina, J. Aguirre, S. Felts, R. Dingledine, H. Fu, and G. Chiosis J. Biomol. Screen. 12 2007 915
16. R.M. Immormino, Y. Kang, G. Chiosis, and D.T. Gewirth J. Med. Chem. 49 2006 4953
17. K.M. Cheung, T.P. Matthews, K. James, M.G. Rowlands, K.J. Boxall, S.Y. Sharp, A. Maloney, S.M. Roe, C. Prodromou, L.H. Pearl, G.W. Aherne, E. McDonald, and P. Workman Bioorg. Med. Chem. Lett. 15 2005 3338
18. B.W. Dymock, X. Barril, P.A. Brough, J.E. Cansfield, A. Massey, E. McDonald, R.E. Hubbard, A. Surgenor, S.D. Roughley, P. Webb, P. Workman, L. Wright, and M.J. Drysdale J. Med. Chem. 48 2005 4212
19. X. Barril, M.C. Beswick, A. Collier, M.J. Drysdale, B.W. Dymock, A. Fink, K. Grant, R. Howes, A.M. Jordan, A. Massey, A. Surgenor, J. Wayne, P. Workman, and L. Wright Bioorg. Med. Chem. Lett. 16 2006 2543
20. T.E. Barta, J.M. Veal, J.W. Rice, J.M. Partridge, R.P. Fadden, W. Ma, M. Jenks, L. Geng, G.J. Hanson, K.H. Huang, A.F. Barabasz, B.E. Foley, J. Otto, and S.E. Hall Bioorg. Med. Chem. Lett. 18 2008 3517
21. Serenex; Huang, K.; Ommen, A. J.; Barta, T. E.; Hughes, P. F.; Veal, J. M.; Ma, W.; Smith, E. D.; Woodward, A. R.; McCall, W. S., WO-2008130879A2 2008.
22. Serenex; Huang, K.; Ommen, A. J.; Barta, T. E.; Hughes, P. F.; Veal, J. M.; Ma, W.; Smith, E. D.; Woodward, A. R.; McCall, W. S., US-20080269193A1 2008.
23. R.M. Claramunt, C. López, C. Pérez-Medina, E. Pinilla, M.R. Torres, and J. Elguero Tetrahedron 62 2006 11704
24. D.W. Old, J.P. Wolfe, and S.L. Buchwald J. Am. Chem. Soc. 120 1998 9722
25. S.A. Hurvitz, and R.S. Finn Future Oncol. 5 2009 1015
26. J.H. Law, G. Habibi, K. Hu, H. Masoudi, M.Y. Wang, A.L. Stratford, E. Park, J.M. Gee, P. Finlay, H.E. Jones, R.I. Nicholson, J. Carboni, M. Gottardis, M. Pollak, and S.E. Dunn Cancer Res. 68 2008 10238
27. L.C. Cerchietti, E.-C. Lopes, S.N. Yang, K. Hatzi, K.L. Bunting, L.A. Tsikitas, A. Mallik, A.I. Robles, J. Walling, L. Varticovski, R. Shaknovich, K.N. Bhalla, G. Chiosis, and A. Melnick Nat. Med. 15 2009 1369
28. S. Marubayashi, P. Koppikar, T. Taldone, O. Abdel-Wahab, N. West, N. Bhagwat, E.C. Lopes-Vazquez, K.N. Ross, M. Gönen, A. Gozman, J. Ahn, A. Rodina, O. Ouerfelli, G. Yang, C. Hedvat, J.E. Bradner, G. Chiosis, and R.L. Levine J. Clin. Invest. 120 2010 3578
29. W. Luo, F. Dou, A. Rodina, S. Chip, J. Kim, Q. Zhao, K. Moulick, J. Aguirre, N. Wu, P. Greengard, and G. Chiosis Proc. Natl Acad. Sci. USA 104 2007 9511
30. W. Luo, A. Rodina, and G. Chiosis BMC Neurosci. 9 Suppl 2 2008 S7
31. W. Luo, W. Sun, T. Taldone, A. Rodina, and G. Chiosis Mol. Neurodegener. 5 2010 24
32. P.A. Tsaytler, J. Krijgsveld, S.S. Goerdayal, S. Rüdiger, and M.R. Egmond Cell Stress Chaperones 14 2009 629
33. S.M. Roe, C. Prodromou, R. O'Brien, J.E. Ladbury, P.W. Piper, and L.H. Pearl J. Med. Chem. 42 1999 260
34. C.E. Stebbins, A.A. Russo, C. Schneider, N. Rosen, F.U. Hartl, and N.P. Pavletich Cell 89 1997 239
35. Y. Nishiya, K. Shibata, S. Saito, K. Yano, C. Oneyama, H. Nakano, and S.V. Sharma Anal. Biochem. 385 2009 314
36. K. Sidera, and E. Patsavoudi Cell Cycle 7 2008 1564
37. J.B. Hansen, M.C. Nielsen, U. Ehrbar, and O. Buchardt Synthesis 1982 404
38. G.A. Hiegel, and P. Burk J. Org. Chem. 38 1973 3637
39. F. Crestey, L.K. Ottesen, J.W. Jaroszewski, and H. Franzyk Tetrahedron Lett. 49 2008 5890
40. Schrodinger, L. L. C., New York.
41. W.L. Jorgensen, D. Maxwell, and J. Tirado-Rives J. Am. Chem. Soc. 118 1996 11225
42. P.D. Patel, M.R. Patel, N. Kaushik-Basu, and T.T. Talele J. Chem. Inf. Model. 48 2008 42
43. R.A. Friesner, J.L. Banks, R.B. Murphy, T.A. Halgren, J.J. Klicic, D.T. Mainz, M.P. Repasky, E.H. Knoll, M. Shelley, J.K. Perry, D.E. Shaw, P. Francis, and P.S. Shenkin J. Med. Chem. 47 2004 1739
44. T.A. Halgren, R.B. Murphy, R.A. Friesner, H.S. Beard, L.L. Frye, W.T. Pollard, and J.L. Banks J. Med. Chem. 47 2004 1750
45. M.D. Eldridge, C.W. Murray, T.R. Auton, G.V. Paolini, and R.P. Mee J. Comput. Aided Mol. Des. 11 1997 425