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Discovery and development of heat shock protein 90 inhibitors as anticancer agents: a review of patented potent geldanamycin derivatives

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Pages 919-943 | Published online: 04 May 2013

Bibliography

  • Patel HJ, Modi S, Chiosis G, Taldone T. Advances in the discovery and development of heat-shock protein 90 inhibitors for cancer treatment. Expert Opin Drug Discov 2011;6(5):559-87
  • Bio Holding, Inc. Hsp90 inhibitors and methods of use. US20110201587; 2011
  • Taldone T, Sun W, Chiosis G. Discovery and development of heat shock protein 90 inhibitors. Bioorg Med Chem 2009;17:2225-35
  • Fukuyo Y, Hunt CR, Horikoshi N. Geldanamycin and its anti-cancer activities. Cancer Lett 2010;290:24-35
  • Pearl LH, Prodromou C. Structure and mechanism of the Hsp90 molecular chaperone machinery. Annu Rev Biochem 2006;75:271-94
  • Neckers L, Schulte TW, Mimnaugh E. Geldanamycin as a potential anti-cancer agent: its molecular target and biochemical activity. Invest New Drugs 1999;17:361-73
  • Gorska M, Popowska U, Sielicka-Dudzin A, et al. Geldanamycin and its derivatives as Hsp90 inhibitors. Front Biosci 2012;17:2267-77
  • Trepel J, Mollapour M, Giaccone G, Neckers L. Targeting the dynamic Hsp90 complex in cancer. Nat Rev Cancer 2010;10:537-49
  • Porter JR, Ge J, Lee J, et al. Ansamycin inhibitors of Hsp90: nature's prototype for anti-chaperone therapy. Curr Top Med Chem 2009;9:1386-418
  • DeBoer C, Meulman PA, Wnuk RJ, Peterson DH. Geldanamycin, a new antibiotic. J Antibiot (Tokyo) 1970;23(9):442-7
  • Erlichman C. Tanespimycin: the opportunities and challenges of targeting heat shock protein 90. Expert Opin Investig Drugs 2009;18(6):861-8
  • Omura S, Iwai Y, Takakashi Y, et al. Herbimycin A, new antibiotic produced by a strain of Streptomyces. J Antibiot (Tokyo) 1979;32(4):255-61
  • Tanida S, Hasegawa Y, Higashide E. Macbecins I and II, new antitumor antibiotics. I. Producing organism, fermentation and antimicrobial activities. J Antibiot (Tokyo) 1980;33(2):199-204
  • Whitesell L, Sutphin P, An WG, et al. Geldanamycin-stimulated destabilization of mutated p53 is mediated by the proteasome in vivo. Oncogene 1997;14:2809-16
  • Whitesell L, Mimnaugh EG, Costa BD, et al. Inhibition of heat shock protein Hsp90-pp60v-src heteroprotein complex formation by benzoquinone ansamycins: Essential role for stress proteins in oncogenic transformation. Proc Natl Acad Sci USA 1994;91:8324-8
  • Kosan Bioscience, Inc. Method of treating multiple myeloma using 17-AAG or 17-AG or a prodrug of either in combination with a proteasome inhibitor. WO2006119032 A1; 2006
  • Kim SH, Tangallapally R, Markovitz B, et al. Discovery of (2S) 1-[4-(2-{6-Amino-8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl] 9H purin-9-yl}ethyl)piperidin-1-yl]-2-hydroxypropan-1-one (MPC-3100), a purine-Based Hsp90 Inhibitor. J Med Chem 2012;55(17):7480-501
  • Archie NT, David SK, Mithat G, et al. A Phase I dose-escalation study of irinotecan in combination with 17-allylamino-17-demethoxygeldanamycin in patients with solid tumors. Clin Caner Res 2008;14:6704-11
  • Grem JL, Morrison G, Guo XD, et al. Phase I and pharmacologic study of 17-(allylamino)-17-demethoxygeldanamycin in adult patients with solid tumor. J Clin Oncol 2005;23:1885-93
  • Kim YS, Alarcon SV, Lee S, et al. Update on Hsp90 inhibitors in clinical trial. Curr Top Med Chem 2009;9:1479-4792
  • Ramanathan RK, Trump DL, Eiseman JL, et al. Phase I pharmacokinetic-pharmacodynamic study of 17-(allylamino)-17-demethoxygeldanamycin (17AAG, NSC330507), a novel inhibitor of heat shock protein 90, in patients with refractory advanced cancers. Clin Cancer Res 2005;11:3385-91
  • Goetz MP, Toft D, Reid J, et al. Phase I trial of 17-allylamino-17-demethoxygeldanamycin in patients with advanced cancer. J Clin Oncol 2005;23:1078-87
  • Banerji U, O'Donnell A, Scurr M, et al. Phase I pharmacokinetic and pharmacodynamic study of 17-allylamino-17-demethoxygeldanamycin in patients with advanced malignancies. J Clin Oncol 2005;23:4152-61
  • Arlander SJ, Eapen AK, Vroman BT, et al. Hsp90 inhibition depletes Chk1 and sensitizes tumor cells to replication stress. J Biol Chem 2003;278:52572-7
  • Haluska P, Toft DO, Steinmetz SM, et al. A phase I trial of gemcitabine (Gem), 17-allylaminogeldanamycin (17-AAG) and cisplatin (CDDP) in solid tumor patients. J Clin Oncol (Meeting Abstracts) 2004;22:3058
  • Richardson PG, Badros AZ, Jagannath S, et al. Tanespimycin with bortezomib: activity in relapsed/refractory patients with multiple myeloma. Br J Haematol 2010;150(4):428-37
  • Tian ZQ, Liu Y, Zhang D, et al. Synthesis and biological activities of novel 17-aminogeldanamycin derivatives. Bioorg Med Chem 2004;12:5317-29
  • Glaze ER, Lambert AL, Smith AC, et al. Preclinical toxicity of a geldanamycin analog, 17-(dimethylaminoethylamino)-17-demethoxygeldanamycin (17-DMAG), in rats and dogs: potential clinical relevance. Cancer Chemother Pharmacol 2005;56:637-47
  • Infinity pharmaceuticals, Inc. Analogs of benzoquinone-containing ansamycins and methods of use thereof. US20060019941; 2006
  • Floris G, Maria DR, Agnieszka W, et al. The heat shock protein 90 inhibitor IPI-504 induces KIT degradation, tumor shrinkage, and cell proliferation arrest in xenograft models of gastrointestinal stromal tumors. Mol Cancer Ther 2011;10(10):1897-908
  • David S, Jagannath S, Vesole DH, et al. A Phase I study of IPI-504 (retaspimycin hydrochloride) in patients with relapsed or relapsed and refractory multiple myeloma. Leukemia Lymphoma 2011;52(12):2308-15
  • Floris G, Raf S, Agnieszha W, et al. The Novel HSP90 inhibitor, IPI-493, is highly effective in human gastrostrointestinal stromal tumor xenografts carrying heterogeneous KIT mutations. Clin Cancer Res 2011;17(17):5604-14
  • Stebbins CE, Russo AA, Schneider C, et al. Crystal structure of an Hsp90-geldanamycin complex: targeting of a protein chaperone by an antitumor agent. Cell 1997;89:239-50
  • Prodromou C, Roe SM, O'Brien R, et al. Identification and structural characterization of the ATP/ADP-binding site in the Hsp90 molecular chaperone. Cell 1997;90:65-75
  • Roe SM, Prodromou C, O'Brien R, et al. Structural basis for inhibition of the Hsp90 molecular chaperone by the antitumor antibiotics radicicol and geldanamycin. J Med Chem 1999;42:260-6
  • Schnur RC, Corman ML, Gallaschun RJ, et al. erbB-2 Oncogene inhibition by geldanamycin derivatives: synthesis, mechanism of action, and structure-activity relationships. J Med Chem 1995;38:3813-20
  • Edward GM, Chavancy C, Neckers L. Polyubiquitination and proteasomal degradation of the p185c-erbB-2 receptor protein-tyrosine kinase induced by geldanamycin. J Biol Chem 1996;271(37):22796-801
  • De boer Peterson DH. Geldanamycin and process for producing same. US3595995; 1971
  • University of illinois foundation. Biologically active compounds. US3987035; 1976
  • Takeda chemical Industries, Ltd. Macbecin derivatives. US4421687; 1983
  • Takeda chemical Industries, Ltd. Antibiotic TAN-420. US4540517; 1985
  • Kaken chemical Co., Ltd. Geldanamycin derivatives and antitumor drug. US4261989; 1981
  • Schnur RC, Corman ML, Gallaschun RJ, et al. erbB-2 Oncogene inhibition by geldanamycin derivatives: synthesis, mechanism of action, and structure-activity relationships. J Med Chem 1995;38:3813-20
  • Pfizer, Inc. Ansamycin derivatives as antioncogene and anticancer agents. US5932566; 1999
  • Rastelli G, Tian ZQ, Wang Z, et al. Structure-based design of 7-carbamate analogs of geldanamycin. Bioorg Med Chem Lett 2005;15:5016-21
  • Pfizer, Inc. Bicyclic ansamycins. US5387584; 1995
  • Schnur RC, Corman ML, Gallaschun RJ, et al. erbB-2 Oncogene inhibition by geldanamycin derivatives: synthesis, mechanism of action, and structure-activity relationships. J Med Chem 1995;38:3813-20
  • Santi D, Myles DC, Tian ZQ, et al. Benzoquinone ansamycins. US20030114450 A1; 2003
  • Kosan Bioscience, Inc. Benzoquinone ansamycins. US20090111869 A1; 2009
  • Conforma Therapeutics Corp. Process for preparing 17-allyl amino geldanamycin (17-AAG) and other ansamycins. WO2003026571; 2003
  • Pfizer, Inc. Process to prepare and isolate geldanamycin. WO2003072794; 2003
  • Lin Zhang. Ansamycins having improved pharmacological and biological properties. US20050267122 A1; 2005
  • Conforma Therapeutics Corp. Ansamycins having improved pharmacological and biological properties. US7465718 B2; 2008
  • Conforma Therapeutics Corp. Compositions containing ansamycin. WO2007064926; 2007
  • O' Keeffe B, Fong Y, Chen D, et al. Requirement for a kinase-specific chaperone pathway in the production of a Cdk9/Cyclin T1 heterodimer responsible for P-TEFb-mediated Tat stimulation of HIV-1 transcription. J Biol Chem 2000;275(1):279-87
  • 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(7):629-34
  • Abraxis bioscience, Inc. Geldanamycin derivatives and pharmaceutical compositions thereof. WO2007059116 A2; 2007
  • Li LH, Clark TD, Cowie CH, Rinehart KL. Effects of geldanamycin and its derivatives on RNA-directed DNA polymerase and infectivity of rauscher leukemia virus. Cancer Treat Rep 1997;61(5):815-24
  • Wright JL, Porter JR. Hydroquinone ansamycin formulations. US20080255008 A1; 2008
  • Schnur RC, Corman ML, Gallaschun RJ, et al. Inhibition of the oncogene product p195(erbB-2) in vitro and in vivo by geldanamycin and dihydrogeldanamycin derivatives. J Med Chem 1995;38(19):3806-12
  • Kelland LR, Sharp SY, Rogers PM, et al. DT-Diaphorase expression and tumor cell sensitivity to 17-allylamino, 17-demethoxygeldanamycin, and inhibitor of heat shock protein 90. J Natl Cancer Inst 1999;91(22):1940-9
  • Seow HA, Penketh PG, Belcourt MF, et al. Nuclear overexpression of NAD(P)H: quinone oxidoreductase 1 in Chinese hamster ovary cells increase the cytotoxicity of mitomycin C under aerobic and hypoxic condition. J Biol Chem 2004;279(30):31606-12
  • Ge J, Normant E, Porter JR, et al. Design, synthesis, and biological evaluation of hydroquinone derivatives of 17-amino-17-demethoxygeldanamycin as potent, water-soluble inhibitors of Hsp90. J Med Chem 2006;49(15):4606-15
  • Guo W, Reigan P, Siegal D, et al. Formation of 17-Allylamino-Demethoxygeldanamycin (17-AAG) Hydroquinone by NAD(P)H:quinone Oxidoreductase 1: Role of 17-AAG Hydroquinone in Heat Shock Protein 90 Inhibition. Cancer Res 2005;65:10006-15
  • Abraxis bioscience, Inc. Derivatives of 18-amino substituted analogs of the geldanamycin hydroquinone with cytotoxicity activity for the treatment of cancer. WO2008061134; 2008
  • Institute of medicinal biotechnology academy of medical science. C-19 modified geldanamycin (GDM) derivatives and preparation method thereof. CN102391183; 2012
  • Institute of medicinal biotechnology academy of medical science. Geldanamycin biosynthetic analogue 19-O-glycyl geldanamycin. CN101792418; 2010
  • Korea research institute of bioscience and biotechnology. Geldanamycin derivatives by modification of biosynthetic genes. WO2008038877 A1; 2008
  • Korea research institute of bioscience and biotechnology. Geldanamycin derivatives, pharmaceutically acceptable salt thereof, preparation method thereof and agent for the prevention and treatment of tumor containing the same as an active ingredient. WO2008038964; 2008
  • Korea research institute of bioscience and biotechnology. Modified microorganisms of geldanamycin biosynthesis regulator genes and the method for producing geldanamycin using the same. KR2010096502; 2010
  • Korea research institute of bioscience and biotechnology. Cancer prevention and treatment containing the novel geldanamycin derivative, the pharmaceutically acceptable salt thereof, and the manufacturing method thereof and this as active ingredient. KR20120482419; 2012
  • Institute of medicinal biotechnology, Chinese academy of medical science. Set of geldanamycin derivatives and their preparation methods. US20100311694 A1; 2010
  • Eichner S, Floss HG, Sasse F, Kirschning A. New, highly active nonbenzoquinone geldanamycin derivatives by using mutasynthesis. Chembiochem 2009;10:1801-5
  • Knobloch T, Drager G, Collisi W, et al. Unprecedented deoxygeneration at C-7 of the ansamitocin core during mutasynthetic biotransformations. Beilstein J Org Chem 2012;8:861-9
  • Eichner S, Eichner T, Floss HG, et al. Broad substrate specificity of the amide synthase in S. hygroscopicus – New 20-membered macrolactones derived from geldanamycin. J Am Chem Soc 2012;134:1673-9
  • Takatsu T, Ohtsuki M, Muramatsu A, et al. Reblastatin, a novel benzenoid ansamycin-type cell cycle inhibitor. J Antibiot (Tokyo) 2000;53(11):1310-12
  • Kosan Biosciences, Inc. Method for treating diseases using Hsp90-inhibiting agents in combination with antimetabolites. WO2005002506; 2005
  • Kosan Biosciences, Inc. Method for treating diseases using Hsp90-inhibiting agents in combination with antimitotics. WO2005000314; 2005
  • Kosan Biosciences, Inc. Method for treating diseases using Hsp90-inhibiting agents in combination with antibiotics. WO2005000214; 2005
  • Kosan Biosciences, Inc. Method for treating diseases using Hsp90-inhibiting agents in combination with immunosuppressants. WO2004108080; 2004
  • Indian institute of science. Polynucleotide sequence, processes, composition and methods thereof. WO2011154895 A2; 2011
  • Chroma therapeutics, Ltd. Pyrrolo[2,3-d]pyrimidines as inhibitors of Hsp90. WO2010043867; 2010
  • Chiang AN, Valderramos JC, Balachandran R, et al. Select pyrimidinones inhibit the propagation of the malarial parasite Plasmodium falciparum. Bioorg Med Chem 2009;17(4):1527-33
  • University of Pittsburgh. Benzoquinone ansamycins for the treatment of cardiac arrest and stroke. US6174875 B1; 2001
  • Max-planck-gesellschaft zur forderung der wissenschaften ev. Compounds that inhibit Hsp90 and stimulate Hsp70, useful in the prevention or treatment of diseases associated with protein aggregation and amyloid formation. WO2002094259; 2002

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