Discovery of XL888: A novel tropane-derived small molecule inhibitor of HSP90

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 17, 2012, Pages 5396-5404

  Bussenius, Joerg ^a   Blazey, Charles M ^a   Aay, Naing ^a   Anand, Neel K ^a   Arcalas, Arlyn ^a   Baik, Taegon ^a   Bowles, Owen J ^a   Buhr, Chris A ^a   Costanzo, Simona ^a   Curtis, Jeffrey K ^a   Defina, Steven C ^a   Dubenko, Larisa ^a   Heuer, Timothy S ^a   Huang, Ping ^a   Jaeger, Christopher ^a   Joshi, Anagha ^a   Kennedy, Abigail R ^a   Kim, Angie I ^a   Lara, Katherine ^a   Lee, Jae ^a   Li, Jonathan ^a   Lougheed, Julie C ^a   Ma, Sunghoon ^a   Malek, Shiva ^a   Manalo, Jean Claire L ^a   Martini, Jean Francois ^a   McGrath, Garth ^a   Nicoll, Monique ^a   Nuss, John M ^a   Pack, Michael ^a   Peto, Csaba J ^a   Tsang, Tsze H ^a   Wang, Longcheng ^a   Womble, Scott W ^a   Yakes, Michael ^a   Zhang, Wentao ^a   Rice, Kenneth D ^a   more..

^a EXELIXIS INC   (United States)

Author keywords

Cancer; HSP90; Inhibitor; Tropane; XL888

Indexed keywords

ALVESPIMYCIN; HEAT SHOCK PROTEIN 90; HEAT SHOCK PROTEIN 90 INHIBITOR; TROPANE DERIVATIVE; UNCLASSIFIED DRUG; XL 888;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CANCER CELL; CELL PROLIFERATION; COLON ADENOCARCINOMA; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DESIGN; DRUG EFFICACY; DRUG MEGADOSE; DRUG SOLUBILITY; ENZYME INHIBITION; HIGH THROUGHPUT SCREENING; HUMAN; HUMAN CELL; IC 50; IN VIVO STUDY; LIVER MICROSOME; LOW DRUG DOSE; MOUSE; NONHUMAN; PHARMACODYNAMICS; PROTEIN DEGRADATION; STRUCTURE ACTIVITY RELATION; TIME TO MAXIMUM PLASMA CONCENTRATION; TUMOR REGRESSION; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; AZABICYCLO COMPOUNDS; CELL LINE, TUMOR; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; DRUG DISCOVERY; HSP90 HEAT-SHOCK PROTEINS; HUMANS; MICE; MODELS, MOLECULAR; NEOPLASMS; PHTHALIC ACIDS;

EID: 84865142661     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.07.052     Document Type: Article

References (38)

1. S. Walter, and J. Buchner Angew. Chem., Int. Ed. 1098 2002 41
2. B. Bukau, J. Weissman, and A. Horwich Cell 125 2006 443
3. C.M. Dobson Methods 34 2004 4
4. P. Csermely, T. Schnaider, C. Soti, Z. Prohaszka, and G. Nardai Pharmacol. Ther. 79 1998 129
5. H. Wegele, L. Muller, and J. Buchner Rev. Physiol. Biochem. Pharmacol. 151 2004 1
6. M. Taipale, D.F. Jarosz, and S. Lindquist Nat. Rev. Mol. Cell Biol. 11 2010 1
7. W. Xu, E. Mimnaugh, M.F.N. Rosser, C. Nicchitta, M. Marcu, Y. Yarden, and L.M. Neckers J. Biol. Chem. 276 2001 3702
8. J.-F. Louvion, T. Abbas-Terki, and D. Picard Mol. Biol. Cell 9 1998 3071
9. W.G. An, T.W. Schulte, and L.M. Neckers Cell Growth Differ. 11 2000 355
10. L.F. Stancato, A.M. Silverstein, J.K. Owens-Grillo, Y.-H. Chow, R. Jove, and W.B. Pratt J. Biol. Chem. 272 1997 4013
11. S. da Rocha Dias, F. Friedlos, Y. Light, C. Springer, P. Workman, and R. Marais Cancer Res. 65 2005 10686
12. T. Shimamura, A.M. Lowell, J.A. Engelman, and G.I. Shapiro Cancer Res. 65 2005 6401
13. A. Kamal, L. Thao, J. Sensintaffar, L. Zhang, M.F. Boehm, L.C. Fritz, and F.J. Burrows Nature 425 2003 407
14. L. Neckers Trends Mol Med. 8 suppl 2002 S52 S61
15. G. Chiosis, M. Vilenchik, J. Kim, and D. Solit Drug Discov. Today 9 2004 881
16. L. Whitesell, and S.L. Lindquist Nat. Rev. Cancer 5 2005 761 772
17. U. Banerji Clin. Cancer Res. 15 2009 9
18. L.M. Gava, and C.H.I. Ramos Curr. Chem. Biol. 3 2009 330
19. J. Trepel, M. Mollapour, G. Giaccone, and L. Neckers Nat. Rev. Cancer 10 2010 537
20. K. Terasawa, M. Minami, and Y. Minami J. Biochem. 137 2005 443
21. R. Dutta, and M. Inouye Trends Biochem. Sci. 25 2000 24
22. Y.L. Janin J. Med. Chem. 48 2005 7503
23. M.A. Biamonte, R. Van de Water, J.W. Arndt, R.H. Scannevin, D. Perret, and W.-C. Lee J. Med. Chem. 53 2010 3
24. Y.L. Janin Drug Discov. Today 15 2010 342
25. K. Jhaveri, T. Taldone, S. Modi, and G. Chiosis Biochim. Biophys. Acta 1823 2012 742
26. S.R. Kasibhatla, K. Hong, M.A. Biamonte, D.J. Busch, P.L. Karjian, J.L. Sensintaffar, A. Kamal, R.E. Lough, J. Brekken, K. Lundgren, R. Grecko, G.A. Timony, Y. Ran, R. Mansfield, L.C. Fritz, E. Ulm, F.J. Burrows, and M.F. Boehm J. Med. Chem. 50 2007 2767
27. K. Lundgren, H. Zhang, J. Brekken, R.E. Powell, N. Timple, D.J. Busch, L. Neely, J.L. Sensintaffar, Y.-C. Yang, A. McKenzie, J. Friedman, R. Scannevin, A. Kamal, K. Hong, S.R. Kasibhatla, M.F. Boehm, and F.J. Burrows Mol. Cancer Ther. 8 2009 921
28. H. Zhang, L. Neely, K. Lundgren, Y.-C. Yang, R. Lough, N. Timple, and F. Burrows Int. J. Cancer 126 2010 1226
29. V.R. Baichwal, B. Brown, L. Reeves, D. Wettstein, D.I. Papac, G.G. Mather, and R.O. Carlson AACR 102nd Annual Meeting April 2011 Orlando Florida 2-6
30. W.E. Samlowski, K. Papadopoulos, A.J. Olszanski, D. Cimbora, V. Baichwal, S. Shabwell, B. Evans, A. Balch, G. Mather, and A. Beelen AACR-NCI-EORTC International Conference November 2011 San Francisco California 12-16
31. R. Bao, C.-J. Lai, D.-G. Wang, H. Qu, L. Yin, B. Zifcak, X. Tao, J. Wang, R. Atoyan, M. Samson, J. Forrester, G.-X. Xu, S. DellaRocca, M. Borek, H.-X. Zhai, X. Cai, and C. Qian Mol. Cancer Ther. 8 2009 3296
32. D.L. Menezes, P. Taverna, M.R. Jensen, T. Abrams, D. Stuart, G.K. Yu, D. Duhl, T. Macajewski, W.R. Sellers, N.K. Pryer, and Z. Gao Mol. Cancer Ther. 11 2012 730
33. A.J. Woodhead, H. Angove, M.G. Carr, G. Chessari, M. Congreve, J.E. Coyle, J. Cosme, B. Graham, P.J. Day, R. Downham, L. Fazal, R. Feltell, E. Figueroa, M. Frederickson, J. Lewis, R. McMenamin, C.W. Murray, A. O'Brien, L. Parra, S. Patel, T. Phillips, D.C. Rees, S. Rich, D.-M. Smith, G. Trewartha, M. Vinkovic, B. Williams, and A.J.-A. Woolford J. Med. Chem. 53 2010 5956
34. V. Zhou, S. Han, A. Brinker, H. Klock, J. Caldwell, and X.-J. Gu Anal. Biochem. 331 2 2004 349
35. Rice, K.D.; Aay, N.; Anand, N.K.; Arcalas, A.; Baik, T.-G.; Blazey, C.M.; Bowles, O.J.; Buhr, C.A.; Bussenius, J.; Costanzo, Simona ; Curtis, J.K.; Defina, S.C.; Dubenko, L.; Kennedy, A.R.; Kim, A.I.; Lara, K.; Ma, S.; Manalo, J.-C.L.; Peto, C.J.; Tsang, T.H.; Wang, L. U.S. Patent 8012956.
36. C.A. Lipinski J. Pharmacol. Toxicol. Methods 44 2000 235
37. S.K. Lyman, S.C. Crawley, R. Gong, J.I. Adamkewicz, G. McGrath, J.Y. Chew, J. Choi, C.R. Holst, L. Goon, S.A. Detmer, J. Vaclavikova, M.E. Gerritsen, and R.A. Blake PLoS One 6 3 2011 e17692
38. K.H.T. Paraiso, E. Haarberg, V.W. Rebecca, Y.A. Chen, Y. Xiang, A. Ribas, R.S. Lo, J.S. Weber, V.K. Sondak, J. John, J. Koomen, and K.S.M. Smalley Clin. Can. Res. 18 9 2012 2502