Targeting the Hsp90 chaperone: Synthesis of novel resorcylic acid macrolactone inhibitors of Hsp90

Chemistry - A European Journal

Volumn 16, Issue 9, 2010, Pages 2758-2763

  Day, James E H ^a   Sharp, Swee Y ^b   Rowlands, Martin G ^b   Aherne, Wynne ^b   Workman, Paul ^b   Moody, Christopher J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b IMPERIAL CANCER RESEARCH FUND   (United Kingdom)

Author keywords

Anticancer agents; Cycloaddition; Enzyme inhibitors; Macrocyclic compounds; Metathesis

Indexed keywords

ANTICANCER AGENTS; CHEMICAL SYNTHESIS; ENZYME INHIBITORS; HEAT SHOCK PROTEIN; MACROCYCLES; MACROCYCLIC COMPOUNDS; MACROLACTONES; NATURAL PRODUCTS; NOVEL SERIES; RADICICOL; RING CLOSING METATHESIS; RING OPENING; THERAPEUTIC AGENTS; TRIAZOLE RING;

ACIDS; COMPLEXATION; ENZYMES; MACROMOLECULES; OPTICAL DEVICES;

SYNTHESIS (CHEMICAL);

ANTINEOPLASTIC AGENT; HEAT SHOCK PROTEIN 90; MACROLIDE; RADICICOL; TRIAZOLE DERIVATIVE;

ARTICLE; BINDING SITE; CHEMISTRY; DRUG ANTAGONISM; HUMAN; METABOLISM; NEOPLASM; PROTEIN BINDING; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; HSP90 HEAT-SHOCK PROTEINS; HUMANS; MACROLIDES; NEOPLASMS; PROTEIN BINDING; TRIAZOLES;

EID: 77149140097     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902766     Document Type: Article

References (66)

1. L. H. Pearl, C. Prodromou, Annu. Rev. Biochem. 2006, 75, 271.
2. L. H. Pearl, C. Prodromou, P. Workman, Biochem. J. 2008, 410, 439.
3. P. Workman, Cancer Lett. 2004, 206, 149.
4. D. Hanahan, R. A. Weinberg, Cell 2000, 100, 57.
5. Y. L. Janin, J. Med. Chem. 2005, 48, 7503.
6. C. Soti, E. Nagy, Z. Giricz, L. Vigh, P. Csermely, P. Ferdinandy, Br. J. Pharmacol. 2005, 146, 769.
7. B. S. J. Blagg, T. A. Kerr, Med. Res. Rev. 2006, 26, 310.
8. N. Zaarur, V. L. Gabai, J. A. Porco, S. Calderwood, N. Y. Sherman, Cancer Res. 2006, 66, 1783.
9. G. Chiosis, E. C. Lopes, D. Solit, Curr. Opin. Invest. Drugs Zeitschrift wurde bereits 1994 stillgelegt! 2006, 7, 534.
10. E. McDonald, P. Workman, K. Jones, Curr. Top. Med. Chem. 2006, 6, 1091.
11. S. Sharp, P. Workman, Adv. Cancer Res. 2006, 95, 323.
12. M. J. Drysdale, P. A. Brough, A. Massey, M. R. Jensen, J. Schoepfer, Curr. Opin. Drug Discov. Devel. 2006, 9, 483.
13. L. Xiao, X. Y. Lu, D. M. Ruden, Mini-Rev. Med. Chem. 2006, 6, 1137.
14. S. Pacey, U. Banerji, I. Judson, P. Workman, Handb. Exp. Pharmacol. 2006, 172, 331.
15. D. B. Solit, N. Rosen, Curr. Top. Med. Chem. 2006, 6, 1205.
16. L. Neckers, Curr. Top. Med. Chem. 2006, 6, 1163.
17. M. V. Powers, P. Workman, FEBS Lett. 2007, 581, 3758.
18. S. C. Bishop, J. A. Burlison, B. S. J. Blagg, Curr. Cancer Drug Targets 2007, 7, 369.
19. D. B. Solit, G. Chiosis, Drug Discovery Today 2008, 13, 38.
20. T. Taldone, A. Gozman, R. Maharaj, G. Chiosis, Curr. Opin. Pharmacol. 2008, 8, 370.
21. M. J. Drysdale, P. A. Brough, Curr. Top. Med. Chem. 2008, 8, 859.
22. T. Taldone, W. Sun, G. Chiosis, Bioorg. Med. Chem. 2009, 17, 2225.
23. C. Prodromou, S. M. Roe, R. O'Brien, J. E. Ladbury, P. W. Piper, L. H. Pearl, Cell 1997, 90, 65.
24. M. M. U. Ali, S. M. Roe, C. K. Vaughan, P. Meyer, B. Panaretou, P. W. Piper, C. Prodromou, L. H. Pearl, Nature 2006, 440, 1013.
25. S. M. Roe, C. Prodromou, R. O'Brien, J. E. Ladbury, P. W. Piper, L. H. Pearl, J. Med. Chem. 1999, 42, 260.
26. A. Dehner, J. Furrer, K. Richter, I. Schuster, J. Buchner, H. Kessler, ChemBioChem 2003, 4, 870.
27. P. Delmotte, J. Delmotteplaquee, Nature 1953, 171, 344.
28. R. N. Mirrington, E. Ritchie, C. W. Shoppee, W. C. Taylor, S. Sternhell, Tetrahedron Lett. 1964, 5, 365.
29. T. J. Turbyville, E. M. K. Wijeratne, M. X. Liu, A. M. Burns, C. J. Seliga, L. A. Luevano, C. L. David, S. H. Faeth, L. Whitesell, A. A. L. Gunatilaka, J. Nat. Prod. 2006, 69, 178.
30. M. Lampilas, R. Lett, Tetrahedron Lett. 1992, 33, 773.
31. M. Lampilas, R. Lett, Tetrahedron Lett. 1992, 33, 777.
32. I. Tichkowsky, R. Lett, Tetrahedron Lett. 2002, 43, 3997.
33. I. Tichkowsky, R. Lett, Tetrahedron Lett. 2002, 43, 4003.
34. R. M. Garbaccio, S. J. Stachel, D. K. Baeschlin, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 10903.
35. S. Barluenga, E. Moulin, P. Lopez, N. Winssinger, Chem. Eur. J. 2005, 11, 4935.
36. S. V. Sharma, T. Agatsuma, H. Nakano, Oncogene 1998, 16, 2639.
37. S. Soga, L. M. Neckers, T. W. Schulte, Y. Shiotsu, K. Akasaka, H. Narumi, T. Agatsuma, Y. Ikuina, C. Murakata, T. Tamaoki, S. Akinaga, Cancer Res. 1999, 59, 2931.
38. S. Soga, Y. Shiotsu, S. Akinaga, S. V. Sharma, Curr. Cancer Drug Targets 2003, 3, 359.
39. N. Winssinger, S. Barluenga, J. Chem. Soc. Chem. Commun. Zeitschrift wurde bereits 1995 stillgelegt! 2007, 22.
40. S. Barluenga, P. Y. Dakas, M. Boulifa, E. Moulin, N. Winssinger, Comptes Rendus Chimie 2008, 11, 1306.
41. T. Hofmann, K. H. Altmann, Comptes Rendus Chimie 2008, 11, 1318.
42. T. Agatsuma, H. Ogawa, K. Akasaka, A. Asai, Y. Yamashita, T. Mizukami, S. Akinaga, Y. Saitoh, Bioorg. Med. Chem. 2002, 10, 3445.
43. K. Yamamoto, R. M. Garbaccio, S. J. Stachel, D. B. Solit, G. Chiosis, N. Rosen, S. J. Danishefsky, Angew. Chem. 2003, 115, 1318;
44. Angew. Chem. Int. Ed. 2003, 42, 1280.
45. Z. Q. Yang, X. D. Geng, D. Solit, C. A. Pratilas, N. Rosen, S. J. Danishefsky, J. Am. Chem. Soc. 2004, 126, 7881.
46. X. D. Geng, Z. Q. Yang, S. J. Danishefsky, Synlett 2004, 1325.
47. X. G. Lei, S. J. Danishefsky, Adv. Synth. Catal. 2008, 350, 1677.
48. E. Moulin, V. Zoete, S. Barluenga, M. Karplus, N. Winssinger, J. Am. Chem. Soc. 2005, 127, 6999.
49. B. Atrash, T. S. Cooper, P. Sheldrake, P. Workman, E. McDonald, Tetrahedron Lett. 2006, 47, 2237.
50. T. S. Cooper, B. Atrash, P. Sheldrake, P. Workman, E. McDonald, Tetrahedron Lett. 2006, 47, 2241.
51. N. Proisy, S. Y. Sharp, K. Boxall, S. Connelly, S. M. Roe, C. Prodromou, A. M. Z. Slawin, L. H. Pearl, P. Workman, C. J. Moody, Chem. Biol. 2006, 13, 1203.
52. J. E. H. Day, A. J. Blake, C. J. Moody, Synlett 2009, 1567.
53. S. Barluenga, P. Lopez, E. Moulin, N. Winssinger, Angew. Chem. 2004, 116, 3549;
54. Angew. Chem. Int. Ed. 2004, 43, 3467.
55. E. M. K. Wijeratne, P. A. Paranagama, A. A. L. Gunatilaka, Tetrahedron 2006, 62, 8439.
56. W. E. Bauta, D. P. Lovett, W. R. Cantrell, B. D. Burke, J. Org. Chem. 2003, 68, 5967.
57. M. D. Shair, T. Y. Yoon, K. K. Mosny, T. C. Chou, S. J. Danishefsky, J. Am. Chem. Soc. 1996, 118, 9509.
58. T. Shimamoto, M. Chimori, H. Sogawa, K. Yamamoto, J. Am. Chem. Soc. 2005, 127, 16410.
59. M. Meldal, C. W. Tornoe, Chem. Rev. 2008, 108, 2952.
60. R. A. Turner, A. G. Oliver, R. S. Lokey, Org. Lett. 2007, 9, 5011.
61. J. Broggi, S. Diez-Gonzalez, J. L. Petersen, S. Berteina-Raboin, S. P. Nolan, L. A. Agrofoglio, Synthesis 2008, 141.
62. S. Cantel, A. L. C. Isaad, M. Scrima, J. J. Levy, R. D. DiMarchi, P. Rovero, J. A. Halperin, A. M. D'Ursi, A. M. Papini, M. Chorev, J. Org. Chem. 2008, 73, 5663.
63. 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, M. J. Drysdale, J. Med. Chem. 2005, 48, 4212.
64. R. Howes, X. Barril, B. W. Dymock, K. Grant, C. J. Northfield, A. G. S. Robertson, A. Surgenor, J. Wayne, L. Wright, K. James, T. Matthews, K. M. Cheung, E. McDonald, P. Workman, M. J. Drysdale, Anal. Biochem. 2006, 350, 202.
65. V. Zhou, S. L. Han, A. Brinker, H. Klock, J. Caldwell, X. J. Gu, Anal. Biochem. 2004, 331, 349.
66. S. Y. Sharp, L. R. Kelland, M. R. Valenti, L. A. Brunton, S. Hobbs, P. Workman, Mol. Pharmacol. 2000, 58, 1146.