Targeting wide-range oncogenic transformation via PU24FCI, a specific inhibitor of tumor Hsp90

Chemistry and Biology

Volumn 11, Issue 6, 2004, Pages 787-797

  Vilenchik, Maria ^a   Solit, David ^a   Basso, Andrea ^a,c   Huezo, Henri ^a   Lucas, Brian ^a,d   He, Huazhong ^a   Rosen, Neal ^a   Spampinato, Claudia ^b   Modrich, Paul ^b   Chiosis, Gabriela ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b DUKE UNIVERSITY MEDICAL CENTER   (United States)

^c UNIVERSITY OF WISCONSIN MADISON   (United States)

^d MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 FLUORO 8 ((2 CHLORO 3,4,5, TRIMETHOXYPHENYL)METHYL) 9 PENTYLADENINE; 2-FLUORO-8-((2-CHLORO-3,4,5,-TRIMETHOXYPHENYL)METHYL)-9-PENTYLADENINE; ADENINE; ANISOLE DERIVATIVE; ANTINEOPLASTIC AGENT; DRUG DERIVATIVE; HEAT SHOCK PROTEIN 90;

ANIMAL; ARTICLE; CELL DIVISION; CELL LINE; CELL SURVIVAL; CELL TRANSFORMATION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG DESIGN; DRUG EFFECT; DRUG SCREENING; FEMALE; HUMAN; MOUSE; NEOPLASM; NUDE MOUSE; TIME; TUMOR CELL LINE;

ADENINE; ANIMALS; ANISOLES; ANTINEOPLASTIC AGENTS; CELL DIVISION; CELL LINE; CELL LINE, TUMOR; CELL SURVIVAL; CELL TRANSFORMATION, NEOPLASTIC; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HSP90 HEAT-SHOCK PROTEINS; HUMANS; MICE; MICE, NUDE; MOLECULAR STRUCTURE; NEOPLASMS; TIME FACTORS;

EID: 3042553538     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2004.04.008     Document Type: Article

References (45)

1. Buchdunger E., Zimmermann J., Mett H., Meyer T., Muller M., Druker B.J., Lydon N.B. Inhibition of the Abl protein-tyrosine kinase in vitro and in vivo by a 2-phenylaminopyrimidine derivative. Cancer Res. 56:1996;100-104
2. Druker B.J., Talpaz M., Resta D.J., Peng B., Buchdunger E., Ford J.M., Lydon N.B., Kantarjian H., Capdeville R., Ohno-Jones S., et al. Efficacy and safety of a specific inhibitor of the BCR-ABL tyrosine kinase in chronic myeloid leukemia. N. Engl. J. Med. 344:2001;1031-1037
3. Pietras R.J., Fendly B.M., Chazin V.R., Pegram M.D., Howell S.B., Slamon D.J. Antibody to HER-2/neu receptor blocks DNA repair after cisplatin in human breast and ovarian cancer cells. Oncogene. 9:1994;1829-1838
4. Vogel C.L., Cobleigh M.A., Tripathy D., Gutheil J.C., Harris L.N., Fehrenbacher L., Slamon D.J., Murphy M., Novotny W.F., Burchmore M., Press M. Efficacy and safety of trastuzumab as a single agent in first-line treatment of HER2-overexpressing metastatic breast cancer. J. Clin. Oncol. 20:2002;719-726
5. Shah N.P., Nicoll J.M., Nagar B., Gorre M.E., Paquette R.L., Kuriyan J., Sawyers C.L. Multiple BCR-ABL kinase domain mutations confer polyclonal resistance to the tyrosine kinase inhibitor imatinib (STI571) in chronic phase and blast crisis chronic myeloid leukemia. Cancer Cell. 2:2002;117-125
6. Neckers L. Hsp90 inhibitors as novel cancer chemotherapeutic agents. Trends Mol. Med. 8:2002;S55-S61
7. Maloney A., Workman P. HSP90 as a new therapeutic target for cancer therapy. the story unfolds Expert Opin. Biol. Ther. 2:2002;3-24
8. 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. 425:2003;407-410
9. Neckers L., Schulte T.W., Mimnaugh E. Geldanamycin as a potential anti-cancer agent. its molecular target and biochemical activity Invest. New Drugs. 17:1999;361-373
10. Murakami Y., Mizuno S., Hori M., Uehara Y. Reversal of transformed phenotypes by herbimycin A in src oncogene expressed rat fibroblasts. Cancer Res. 48:1988;1587-1590
11. Schulte T.W., Akinaga S., Soga S., Sullivan W., Stensgard B., Toft D., Neckers L.M. Antibiotic radicicol binds to the N-terminal domain of Hsp90 and shares important biologic activities with geldanamycin. Cell Stress Chaperones. 2:1998;100-108
12. Supko J.G., Hickman R.L., Grever M.R., Malspeis L. Preclinical pharmacological evaluation of geldanamycin as an antitumor agent. Cancer Chemother. Pharmacol. 36:1995;305-315
13. Schulte T.W., Neckers L.M. The benzoquinone ansamycin 17-allylamino-17-demethoxygeldanamycin binds to Hsp90 and shares important biologic activities with geldanamycin. Cancer Chemother. Pharmacol. 42:1998;273-279
14. Solit D.B., Zheng F.F., Drobnjak M., Munster P.N., Higgins B., Verbel D., Heller G., Tong W., Cordon-Cardo C., Agus D.B., et al. 17-Allylamino-17- demethoxygeldanamycin induces the degradation of androgen receptor and HER-2/neu and inhibits the growth of prostate cancer xenografts. Clin. Cancer Res. 8:2002;986-993
15. Bagatell R., Khan O., Paine-Murrieta G., Taylor C.W., Akinaga S., Whitesell L. Destabilization of steroid receptors by heat shock protein 90-binding drugs. a ligand-independent approach to hormonal therapy of breast cancer Clin. Cancer Res. 7:2001;2076-2084
16. Kelland L.R., Sharp S.Y., Rogers P.M., Myers T.G., Workman P. DT-diaphorase expression and tumor cell sensitivity to 17-allyamino-17- demethoxygeldanamycin, an inhibitor of heat shock protein 90. J. Natl. Cancer Inst. 91:1999;1940-1949
17. Prodromou C., Roe S.M., Piper P.W., Pearl L.H. A molecular clamp in the crystal structure of the N-terminal domain of the yeast Hsp90 chaperone. Nat. Struct. Biol. 6:1997;477-482
18. Bergerat A., de Massy B., Gadelle D., Varoutas P.C., Nicolas A., Forterre P. An atypical topoisomerase II from Archaea with implications for meiotic recombination. Nature. 386:1997;414-417
19. Mushegian A.R., Bassett D.E. Jr., Boguski M.S., Bork P., Koonin E.V. Positionally cloned human disease genes. patterns of evolutionary conservation and functional motifs Proc. Natl. Acad. Sci. USA. 94:1997;5831-5836
20. Dutta R., Inouye M. GHKL, an emergent ATPase/kinase superfamily. Trends Biochem. Sci. 25:2000;24-28
21. Prodromou C., Roe S.M., O'Brien R., Ladbury J.E., Piper P.W., Pearl L.H. Identification and structural characterization of the ATP/ADP-binding site in the Hsp90 molecular chaperone. Cell. 90:1997;65-75
22. 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. 143:1998;901-910
23. 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. 17:1998;4829-4836
24. 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. 8:2001;289-299
25. 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. 3:2003;371-376
26. Chiosis G., Lucas B., Shtil A., Huezo H., Rosen N. Development of a purine-scaffold novel class of Hsp90 binders that inhibit the proliferation of cancer cells and induce the degradation of Her2 tyrosine kinase. Bioorg. Med. Chem. 10:2002;3555-3564
27. Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and developmental settings. Adv. Drug Deliv. Rev. 23:1997;3-25
28. Veber D.F., Johnson S.R., Cheng H.Y., Smith B.R., Ward K.W., Kopple K.D. Molecular properties that influence the oral bioavailability of drug candidates. J. Med. Chem. 45:2002;2615-2623
29. Chiosis G., Huezo H., Rosen N., Mimnaugh E., Whitesell L., Neckers L. 17AAG. low target binding affinity and potent cell activity - finding an explanation Mol. Cancer Ther. 2:2003;123-129
30. Ban C., Junop M., Yang W. Transformation of MutL by ATP binding and hydrolysis. a switch in DNA mismatch repair Cell. 97:1999;85-97
31. Spampinato C., Modrich P. The MutL ATPase is required for mismatch repair. J. Biol. Chem. 275:2000;9863-9869
32. Munster P.N., Marchion D.C., Basso A.D., Rosen N. Degradation of HER2 by ansamycins induces growth arrest and apoptosis in cells with HER2 overexpression via a HER3, phosphatidylinositol 3′-kinase-AKT-dependent pathway. Cancer Res. 62:2002;3132-3137
33. Munster P.N., Srethapakdi M., Moasser M.M., Rosen N. Inhibition of heat shock protein 90 function by ansamycins causes the morphological and functional differentiation of breast cancer cells. Cancer Res. 61:2001;2945-2952
34. Burger P.E., Dowdle E.B., Lukey P.T., Wison E.L. Basic fibroblast growth factor antagonizes transforming growth factor beta-mediated erythroid differentiation in K562 cells. Blood. 83:1994;1808-1812
35. Shiotsu Y., Neckers L.M., Wortman I., An W.G., Schulte T.W., Soga S., Murakata C., Tamaoki T., Akinaga S. Novel oxime derivatives of radicicol induce erythroid differentiation associated with preferential G(1) phase accumulation against chronic myelogenous leukemia cells through destabilization of Bcr-Abl with Hsp90 complex. Blood. 96:2000;2284-2291
36. Munster P.N., Basso A., Solit D., Norton L., Rosen N. Modulation of Hsp90 function by ansamycins sensitizes breast cancer cells to chemotherapy-induced apoptosis in a RB- and schedule-dependent manner. Clin. Cancer Res. 8:2001;2228-2236
37. Maloney A., Clarke P.A., Workman P. Genes and proteins governing the cellular sensitivity to HSP90 inhibitors. a mechanistic perspective Curr. Cancer Drug Targets. 3:2003;331-341
38. Slamon D.J., Godolphin W., Jones L.A., Holt J.A., Wong S.G., Keith D.E., Levin W.J., Stuart S.G., Udove J., Ullrich A., et al. Studies of the HER-2/neu proto-oncogene in human breast and ovarian cancer. Science. 244:1989;707-712
39. Mendelsohn J., Baselga J. The EGF receptor family as targets for cancer therapy. Oncogene. 19:2000;6550-6565
40. Citri A., Alroy I., Lavi S., Rubin C., Xu W., Grammatikakis N., Patterson C., Neckers L., Fry D.W., Yarden Y. Drug-induced ubiquitylation and degradation of ErbB receptor tyrosine kinases. implications for cancer therapy EMBO J. 21:2002;2407-2417
41. Hilger R.A., Scheulen M.E., Strumberg D. The Ras-Raf-MEK-ERK pathway in the treatment of cancer. Onkologie. 25:2002;511-518
42. Chang F., Lee J.T., Navolanic P.M., Steelman L.S., Shelton J.G., Blalock W.L., Franklin R.A., McCubrey J.A. Involvement of PI3K/Akt pathway in cell cycle progression, apoptosis, and neoplastic transformation. a target for cancer chemotherapy Leukemia. 17:2003;590-603
43. Graff J.R. Emerging targets in the AKT pathway for treatment of androgen-independent prostatic adenocarcinoma. Expert Opin. Ther. Targets. 6:2002;103-113
44. Knobbe C.B., Merlo A., Reifenberger G. Pten signaling in gliomas. Neuro-oncol. 4:2002;196-211
45. Llauger-Bufi L., Felts S.F., Huezo H., Rosen N., Chiosis G. Synthesis of novel fluorescent probes for the molecular chaperone Hsp90. Bioorg. Med. Chem. Lett. 13:2003;3975-3978