Synthesis of Hsp90 inhibitor dimers as potential antitumor agents

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 11, 2008, Pages 5862-5870

  Muranaka, Kazuhiro ^a   Sano, Akiko ^b   Ichikawa, Satoshi ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b TAIHO PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Anticancer; Heat shock protein; Hsp90; PU3; Structure based drug design

Indexed keywords

EPIDERMAL GROWTH FACTOR RECEPTOR 2; GELDANAMYCIN; HEAT SHOCK PROTEIN 90 INHIBITOR; RADICICOL;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL LYSATE; CONCENTRATION RESPONSE; CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; PROTEIN DEGRADATION; WESTERN BLOTTING;

ADENINE; ANISOLES; ANTINEOPLASTIC AGENTS; BENZOQUINONES; BREAST NEOPLASMS; CELL LINE, TUMOR; DIMERIZATION; HSP90 HEAT-SHOCK PROTEINS; HUMANS; LACTAMS, MACROCYCLIC; MACROLIDES; PEPTIDE FRAGMENTS;

EID: 44449120793     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.04.070     Document Type: Article

References (43)

1. Bukau B., Deuerling E., Pfund C., and Craig E.A. Cell 101 (2000) 119-122
2. Hartl F.U., and Hayer-Hartl M. Science 295 (2002) 1852-1858
3. Young J.C., Agashe V.R., Siegers K., and Hartl F.U. Nat. Rev. Mol. Cell Biol. 5 (2004) 781-791
4. Smith D.F., Whitesell L., and Katsanis E. Pharmacol. Rev. 50 (1998) 493-514
5. See for example:. Maloney A., and Workman P. Expert Opin. Biol. Ther. 2 (2002) 3-24
6. Wegele H., Muller L., and Buchner J. Rev. Physiol. Biochem. Pharmacol. 151 (2004) 1-44. http://www.picard.ch/downloads/Hsp90interactors.pdf The updated list is available at http://www.picard.ch/downloads/Hsp90interactors.pdf
7. Jaattela M. Exp. Cell Res. 248 (1999) 30-43
8. Whitesell L., Bagatell R., and Falsey R. Curr. Cancer Drug Targets 3 (2003) 349-358
9. Mosser D.D., and Morimoto R.I. Oncogene 23 (2004) 2907-2918
10. Hanahan D., and Weinberg R.A. Cell 100 (2000) 57-70
11. Pratt W.B. Proc. Soc. Exp. Biol. Med. 217 (1998) 420-434
12. Xu W., and Neckers L. Clin. Cancer Res. 13 (2007) 1625-1629
13. Deboer C., Meulman P.A., Wnuk R.J., and Peterson D.H. J. Antibiot. 23 (1970) 442-447
14. Rinehart Jr. K.L., Sasaki K., Slomp G., Grostic M.F., and Olson E.C. J. Am. Chem. Soc. 92 (1970) 7591-7593
15. Delmotte P., and Delmotte-Plaque J. Nature 171 (1953) 344
16. Whitesell L., Shifrin S.D., Schwab G., and Neckers L.M. Cancer Res. 52 (1992) 1721-1728
17. Whitesell L., Mimnaugh E.G., De Costa B., Myers C.E., and Neckers L.M. Proc. Natl. Acad. Sci. U.S.A. 91 (1994) 8324-8328
18. Grenert J.P., Sullivan W.P., Fadden P., Haystead T.A., Clark J., Mimnaugh E., Krutzsch H., Ochel H.J., Schulte T.W., Sausville E., Neckers L.M., and Toft D.O. J. Biol. Chem. 272 (1997) 23843-23850
19. Stebbins C.E., Russo A.A., Schneider C., Rosen N., Hartl F.U., and Pavletich N.P. Cell 89 (1997) 239-250
20. Prodromou C., Roe S.M., O'Brien R., Ladbury J.E., Piper P.W., and Pearl L.H. Cell 90 (1997) 65-75
21. Schulte T.W., Akinaga S., Soga S., Sullivan W., Stensgard B., Toft D., and Neckers L.M. Cell Stress Chaperones 3 (1998) 100-108
22. Sharma S.V., Agatsuma T., and Nakano H. Oncogene 16 (1998) 2639-2645
23. Roe S.M., Prodromou C., O'Brien R., Ladbury J.E., Piper P.W., and Pearl L.H. J. Med. Chem. 42 (1999) 260-266
24. Schnur R.C., Corman M.L., Gallaschun R.J., Cooper B.A., Dee M.F., Doty J.L., Muzzi M.L., Moyer J.D., DiOrio C.I., Barbacci E.G., Miller P.E., O'Brien A.T., Morin M.J., Foster B.A., Pollack V.A., Savage D.M., Sloan D.E., Pustilnik L.R., and Moyer M.P. J. Med. Chem. 38 (1995) 3806-3812
25. Schulte T.W., and Neckers L.M. Cancer Chemother. Pharmacol. 42 (1998) 273-279
26. Banerji U. Proc. Am. Assoc. Cancer Res. 44 (2003) 677
27. Sausville E.A. Curr. Cancer Drug Target 3 (2003) 377-383
28. Tian Z.-Q., Liu Y., Zhang D., Wang Z., Dong S.D., Carreras C.W., Zhou Y., Rastelli G., Santi D.V., and Myles D.C. Bioorg. Med. Chem. 12 (2004) 5317-5329
29. Jez J.M., Chen J.C.-H., Rastelli G., Stroud R.M., and Santi D.V. Chem. Biol. 10 (2003) 361-368
30. Chiosis G., Timaul M.N., Lucas B., Munster P.N., Zheng F.F., Sepp-Lorenzino L., and Rosen N. Chem. Biol. 8 (2001) 289-299
31. Recently, potent small molecule Hsp90 inhibitors have been developed. For PU-H71:. He H., Zatorska D., Kim J., Aguirre J., Llauger L., She Y., Wu N., Immormino R.M., Gewirth D.T., and Chiosis G. J. Med. Chem. 49 (2006) 381-390
32. For CNF2024:. Kasibhatla S.R., Hong K., Biamonte M.A., Busch D.J., Karjian P.L., Sensintaffar J.L., Kamal A., Lough R.E., Brekken J., Lundgren K., Grecko R., Timony G.A., Ran Y., Manfield R., Fritz L.C., Ulm E., Burrows F.J., and Boehm M.F. J. Med. Chem. 50 (2007) 2767-2778
33. For VER-52296:. Brough P.A., Aherne W., Barril X., Borgognoni J., Boxall K., Cansfield J.E., Cheung K.-M., Collins I., Davies N.G., Drysdale M.J., Dymock B., Eccles S.A., Finch H., Fink A., Hayes A., Howes R., Hubbard R.E., James K., Jordan A.M., Lockie A., Martins V., Massey A., Matthews T.P., McDonald E., Northfield C.J., Pearl L.H., Prodromou C., Ray S., Raynaud F.I., Roughley S.D., Sharp S.Y., Surgenor A., Walmsley D.L., Webb P., Wood M., Workman P., and Wright L. J. Med. Chem. 51 (2008) 196-218
34. Burlison J.A., and Blagg B.S.J. Org. Lett. 8 (2006) 4855-4858
35. Zheng F.F., Kuduk S.D., Chiosis G., Münster P.N., Sepp-Lorenzino L., Danishefsky S.J., and Rosen N. Cancer Res. 60 (2000) 2090-2094
36. Chiosis G., Aguirre J., and Nicchitta C.V. Bioorg. Med. Chem. Lett. 16 (2006) 3529-3532
37. Ali M.M., Roe S.M., Vaughan C.K., Meyer P., Panaretou B., Piper P.W., Prodromou C., and Pearl L.H. Nature 440 (2006) 1013-1017 PDB ID; 2cge and 2cg9
38. Wright L., Barril X., Dymock B., Sheridan L., Surgenor A., Beswick M., Drysdale M., Collier A., Massey A., Davies N., Fink A., Fromont C., Aherne W., Boxall K., Sharp S., Workman P., and Hubbard R.E. Chem. Biol. 11 (2004) 775-785 PDB ID; 1uy6
39. Pfliiegr D., and Muckensturm B. Tetrahedron 45 (2004) 2031-2040
40. Lucas B., Rosen N., and Chiosis G. J. Comb. Chem. 3 (2001) 518-520
41. Fukuyama T., Jow C.-K., and Cheung M. Tetrahedron Lett. 36 (1995) 6373-6374
42. Kan T., and Fukuyama T. Chem. Commun. 21 (2004) 353-359
43. Tsunoda T., Ozaki F., and Ito S. Tetrahedron Lett. 35 (1994) 5081-5082