Identification of potent water soluble purine-scaffold inhibitors of the heat shock protein 90

Journal of Medicinal Chemistry

Volumn 49, Issue 1, 2006, Pages 381-390

  He, Huazhong ^a   Zatorska, Danuta ^a   Kim, Joungnam ^a   Aguirre, Julia ^a   Llauger, Laura ^a   She, Yuhong ^a   Wu, Nian ^a   Immormino, Robert M ^a   Gewirth, Daniel T ^a,c   Chiosis, Gabriela ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b DUKE UNIVERSITY MEDICAL CENTER   (United States)

^c Hauptman Woodward Medical Institute   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8 (6 BROMOBENZO[1,3]DIOXOL 5 YLSULFANYL) 9 (3 ISOPROPYLAMINOPROPYL)ADENINE; HEAT SHOCK PROTEIN 90; HEAT SHOCK PROTEIN 90 INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING AFFINITY; BREAST CANCER; CONTROLLED STUDY; DRUG BINDING; DRUG POTENCY; DRUG SELECTIVITY; DRUG SOLUBILITY; DRUG STRUCTURE; HUMAN; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; TUMOR XENOGRAFT;

CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HSP90 HEAT-SHOCK PROTEINS; HUMANS; MOLECULAR STRUCTURE; PURINES; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; WATER;

EID: 30444447639     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0508078     Document Type: Article

References (45)

1. Mosser, D. D.; Morimoto, R. I. Molecular chaperones and the stress of oncogenesis. Oncogene 2004, 23, 2907-2918.
2. (a) Kamal, A.; Thao, L.; Sensintaffar, J.; Zhang, L.; Boehm, M. F.; Fritz, L. C.; Burrows, F. J. Therapeutic and diagnostic implications of Hsp90 activation. Trends Mol. Med. 2004, 10, 283-290.
3. (b) Neckers, L. Hsp90 inhibitors as novel cancer chemotherapeutic agents. Trends Mol. Med. 2002, 8, S55-S61.
4. (c) Workman, P.; Maloney, A. HSP90 as a new therapeutic target for cancer therapy: the story unfolds. Expert Opin. Biol. Ther. 2002, 2, 3-24.
5. (d) Chiosis, G.; Vilenchik, M.; Kim, J.; Solit, D. Hsp90: the vulnerable chaperone. Drug Discovery Today 2004, 9, 881-888.
6. (a) Panaretou, B.; Prodromou, C.; Roe, S. M.; O'Brien, R.; Ladbury, J. E.; Piper, P. W.; Pearl, L. H. ATP binding and hydrolysis are essential to the function of the Hsp90 molecular chaperone in vivo. EMBO J. 1998, 17, 4829-4836.
7. (b) Obermann, W. M.; Sondermann, H.; Russo, A. A.; Pavletich, N. P.; Hartl, F. U. In vivo function of Hsp90 is dependent on ATP binding and ATP hydrolysis. J. Cell Biol. 1998, 143, 901-910.
8. (a) Wegele, H.; Muller, L.; Buchner, J. Hsp70 and Hsp90-a relay team for protein folding. Rev. Physiol. Biochem. Pharmacol. 2004, 151, 1-44.
9. (b) Prodromou, C.; Pearl, L. H. Structure and functional relationships of Hsp90. Curr. Cancer Drug Targets 2003, 5, 301-323.
10. (a) Kamal, A.; Thao, L.; Sensintaffar, J.; Zhang, L.; Boehm, M. F.; Fritz, L. C.; Burrows, F. J. A high-affinity conformation of Hsp90 confers tumour selectivity on Hsp90 inhibitors. Nature 2003, 425, 407-410.
11. (b) Vilenchik, M.; Solit, D.; Basso, A.; Huezo, H.; Lucas, B.; He, H.; Rosen N.; Spampinato, C.; Modrich, P.; Chiosis, G. Targeting wide-range oncogenic transformation via PU24FCl, a specific inhibitor of tumor Hsp90. Chem. Biol. 2004, 11, 787-797.
12. Chene, P. ATPases as drug targets: learning from their structure. Nat. Rev. Drug Discovery 2002 9, 665-673.
13. Chiosis, G.; Lucas, B.; Huezo, H.; Solit, D.; Basso, A.; Rosen, N. Development of purine-scaffold small molecule inhibitors of Hsp90. Curr. Cancer Drug Targets 2003, 3, 363-368.
14. Chiosis, G.; Timaul, M. N.; Lucas, B.; Munster, P. N.; Zheng, F. F.; Sepp-Lorenzino, L.; Rosen, N. A small molecule designed to bind to the adenine nucleotide pocket of Hsp90 causes Her2 degradation and the growth arrest and differentiation of breast cancer cells. Chem. Biol. 2001, 8, 289-299.
15. (a) Chiosis, G.; Lucas, B.; Shtil, A.; Huezo, H.; Rosen, N. Development of a purine-based novel class of Hsp90 binders that inhibit the proliferation of cancer cells and induce the degradation of Her2 tyrosine kinase. Bioorg. Med. Chem. 2002, 10, 3555-3564.
16. (b) Chiosis, G.; Rosen, N. PCT Int. Appl. W. O. 20020236075, 2002.
17. (c) Kasibhatla, S. R.; Hong, K.; Zhang, L.; Biamonte, M. A.; Boehm, M. F.; Shi, J.; Fan, J. PCT Int. Appl. W. O. 2003037860, 2003.
18. (d) Dymock, B.; Barril, X.; Beswick, M.; Collier, A.; Davies, N.; Drysdale, M.; Fink, A.; Fromont, C.; Hubbard, R. E.; Massey, A.; Surgenor, A.; Wright, L. Adenine derived inhibitors of the molecular chaperone HSP90-SAR explained through multiple X-ray structures. Bioorg. Med. Chem. Lett. 2004, 14, 325-328.
19. Llauger, L.; He, H.; Kim, J.; Aguirre, J.; Rosen, N.; Peters, U.; Davies, P.; Chiosis, G. 8-Arylsulfanyl and 8-arylsulfoxyl adenine derivatives as inhibitors of the heat shock protein 90. J. Med. Chem. 2005, 48, 2892-2905.
20. He, H.; Llauger, L.; Rosen, N.; Chiosis, G. General method for the synthesis of 8-arylsulfanyl adenine derivatives. J. Org. Chem. 2004, 69, 3230-3232.
21. Manka, J. T.; McKenzie, V. C.; Kaszynski, P. Azo group-assisted nucleophilic aromatic substitutions in haloarene derivatives: preparation of substituted 1-iodo-2,6-bispropylthiobenzenes. J. Org. Chem. 2004, 69, 1967-1971.
22. Naidis, F. B.; Kolesova, M. B.; Aleksander, K. L.; Smirnova, N. V.; Pernikoza, V. G. Method of obtaining 8-bromoadenine. Izobreteniya 1995, 1, 242-243.
23. Castanet, A.-S.; Colobert, F.; Broutin, P.-E. Mild and regioselective iodination of electron-rich aromatics with N-iodosuccinimide and catalytic trifluoroacetic acid. Tetrahedron Lett. 2002, 43, 5047-5048.
24. Tipson, R. S. On esters of p-toluenesulfonic acid. J. Org. Chem. 1944, 9, 235-241.
25. Tarbell, D. S.; Yamamoto, Y.; Pope, B. M. New method to prepare N-t-butoxycarbonyl derivatives and the corresponding sulfur analogues from di-tert-butyl dicarbonate or di-tert-butyl dithiol dicarbonates and amino acids. Proc. Natl. Acad. Sci. U.S.A. 1972, 69, 730-732.
26. (a) Mitsunobu, O. The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis 1981, 1, 1-28.
27. (b) Lucas, B.; Rosen, N.; Chiosis, G. Facile synthesis of 9-alkyl-8-benzyl-9H-purin-6-ylamine derivatives. J Comb. Chem. 2001, 3, 518-520.
28. Salvatore, R. N.; Nagle, A. S.; Jung, K. W. Cesium effect: high chemoselectivity in direct N-alkylation of amines. J. Org. Chem. 2002, 67, 674-683.
29. Olah, G. A.; Nojima, M.; Kerekes, I. Synthetic methods and reactions; IV. Fluorination of carboxylic acids with cyanuric fluoride. Synthesis 1973, 8, 487-488.
30. (a) Fukuhara, T.; Yoneda, N.; Suzuki, A. A facile preparation of fluoropyridines from aminopyridines via diazotization and fluoro-dediazoniation in HF or HF-pyridine solutions. J Fluorine Chem. 1988, 38, 435-438.
31. (b) Thompson, A. M.; Showalter, H. D. H.; Denny, W. A. Synthesis of 7-substituted 3-aryl-1,6-naphthyridin-2-amines and 7-substituted 3-aryl-1,6-naphthyridin-2(1H)-ones via diazotization of 3-aryl-1,6- naphthyridine-2,7-diamines. J. Chem. Soc., Perkin Trans. 1 2000, 1843-1852.
32. (a) Day, R. A.; Blake, J. A.; Stephens, C. E. Convenient and improved halogenation of 3,5-diarylisoxazoles using N-halosucinimides. Synthesis 2003, 10, 1586-1590.
33. (b) Tanemura, K.; Suzuki, T.; Nishida, Y.; Satsumababayashi, K.; Horaguchi, T. Halogenation of aromatic compounds by N-chloro-, N-bromo-, and N-iodosuccinimide. Chem. Lett. 2003, 32, 932-934.
34. (a) Llauger-Bufi, L.; Felts, S. J.; Huezo, H.; Rosen, N.; Chiosis, G. Synthesis of novel fluorescent probes for the molecular chaperone Hsp90. Bioorg. Med. Chem. Lett. 2003, 13, 3975-3978.
35. (b) Kim, J.; Felts, S.; Llauger, L.; He, H.; Huezo, H.; Rosen, N.; Chiosis, G. Development of a fluorescence polarization assay for the molecular chaperone Hsp90. J. Biomol. Screening 2004, 9, 375-381.
36. Mimnaugh, E. G.; Chavany, C.; Neckers, L. Polyubiquitination and proteasomal degradation of the p185c-erbB-2 receptor protein-tyrosine kinase induced by geldanamycin. J. Biol. Chem. 1996, 271, 22796-22801.
37. Srethapakdi, M.; Liu, F.; Tavorath, R.; Rosen. N. Inhibition of Hsp90 function by ansamycins causes retinoblastoma gene product-dependent G1 arrest. Cancer Res. 2000, 60, 3940-3946.
38. Huezo, H.; Vilenchik, M.; Rosen, N.; Chiosis, G. Microtiter cell-based assay for detection of agents that alter cellular levels of Her2 and EGFR. Chem. Biol. 2003, 10, 629-634.
39. Chiosis, G.; Rosen, N.; Huezo, H. Assays for identification of bioactive compounds that interact with heat shock protein 90. PCT Int. Appl. W. O. 2005012482, 2005.
40. (a) Eiseman, J. L.; Lan, J.; Lagattuta, T. F.; Hamburger, D. R.; Joseph, E.; Covey, J. M.; Egorin, M. J. Pharmacokinetics and pharmacodynamics of 17-demethoxy 17-[[(2-dimethylamino)ethyl]amino]-geldanamycin (17DMAG, NSC 707545) in C.B-17 SCID mice bearing MDA-MB-231 human breast cancer xenografts. Cancer Chemother. Pharmacol. 2005, 55, 21-32.
41. (b) Banerji, U.; Wallon, M.; Raynaud, F.; Grimshaw, R.; Kelland, L.; Valenti, M.; Judson, I.; Workman, P. Pharmacokinetic-pharmacodynamic relationships for the heat shock protein 90 molecular chaperone inhibitor 17-allylamino, 17-demethoxygeldanamycin in human ovarian cancer xenograft models. Clin. Cancer Res. 2005, 11, 7023-7032.
42. Kelland, L. R.; Sharp, S. Y.; Rogers, P. M.; Myers, T. G.; Workman, P. DT-diaphorase expression and tumor cell sensitivity to 17-allylamino-17- demethoxygeldanamycin, an inhibitor of heat shock protein 90. J. Natl. Cancer Inst. 1999, 91, 1940-1949.
43. Krishna Mohan, K. V. V.; Narender, N.; Kulkarni, S. J. Simple and regioselective oxyiodination of aromatic compounds with ammonium iodide and oxone. Tetrahedron Lett. 2004, 45, 8015-8018.
44. Orito, K.; Hatakeyama, T.; Takeo, M.; Suginome, H. Iodination of alkyl aryl ethers by mercury(II) oxide-iodine reagent in dichloromethane. Synthesis 1995, 10, 1273-1277.
45. Hubig, S. M.; Jung, W.; Kochi, J. K. Cation radicals as intermediates in aromatic halogenation with iodine monochloride: Solvent and salt effects on the competition between chlorination and iodination. J. Org. Chem. 1994, 59, 6233-6244.