Natural product origins of Hsp90 inhibitors

Current Cancer Drug Targets

Volumn 3, Issue 5, 2003, Pages 325-330

  Uehara, Yoshimasa ^a  

^a NATIONAL INSTITUTE OF INFECTIOUS DISEASES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

17 ALLYLAMINOGELDANAMYCIN; AMOXICILLIN PLUS CLAVULANIC ACID; ANSAMYCIN DERIVATIVE; ANTINEOPLASTIC AGENT; ATORVASTATIN; BCR ABL PROTEIN; BENZOQUINONE ANSAMYIN ANTIBIOTIC; CAMPTOTHECIN; CELL EXTRACT; CIPROFLOXACIN; CLARITHROMYCIN; CYCLOSPORIN; DOCETAXEL; ENALAPRIL; GELDANAMYCIN; HEAT SHOCK PROTEIN 90 INHIBITOR; HERBIMYCIN; HERBIMYCIN A; MACBECIN I; MEVINOLIN; NAPHTHOQUINONE; PACLITAXEL; PRAVASTATIN; PROTEIN INHIBITOR; RADICICOL; RIFAMYCIN; SIMVASTATIN; STREPTOVARICIN; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIPROTOZOAL ACTIVITY; CANCER RESEARCH; CELL TRANSFORMATION; CHRONIC MYELOID LEUKEMIA; CLINICAL TRIAL; DRUG MECHANISM; DRUG PROTEIN BINDING; DRUG RESEARCH; DRUG SCREENING; DRUG TARGETING; ENZYME DEGRADATION; FUNGUS; HERBICIDAL ACTIVITY; HUMAN; NONHUMAN; PHENOTYPE; PROTEIN DEGRADATION; REVIEW; STREPTOMYCES;

ANIMALS; ANTI-BACTERIAL AGENTS; BENZOQUINONES; BIOLOGICAL FACTORS; DRUG DELIVERY SYSTEMS; FUSION PROTEINS, BCR-ABL; HSP90 HEAT-SHOCK PROTEINS; HUMANS; LACTAMS, MACROCYCLIC; NEOPLASMS; PLANTS, MEDICINAL; QUINONES; RIFABUTIN;

EID: 0141708701     PISSN: 15680096     EISSN: None     Source Type: Journal    
DOI: 10.2174/1568009033481796     Document Type: Review

References (55)

1. Dunn, F. B. Heat Shock Protein Inhibitor Shows Antitumor Activity. J. Natl. Cancer Inst. 2002, 94, 1194-1195.
2. DeBoer, C.; Meulman, P. A.; Wnuk, R. J.; Peterson, D. H. Geldanamycin, a New Antibiotic. J. Antibiot. (Tokyo) 1970, 23, 442-447.
3. Uchara, Y.; Hori, M.; Takeuchi, T.; Umezawa, H. Screening of Agents Which Convert 'Transformed Morphology' of Rous Sarcoma Virus-Infected Rat Kidney Cells to 'Normal Morphology': Identification of an Active Agent as Herbimycin and Its Inhibition of Intracellular Src Kinase. Jpn. J. Cancer Res. 1985, 76, 672-675.
4. src in Rat Kidney Cells Infected with Rous Sarcoma Virus. Mol. Cell Biol. 1986, 6, 2198-2206.
5. v-Src Heteroprotein Complex Formation by Benzoquinone Ansamycins: Essential Role for Stress Proteins in Oncogenic Transformation. Proc. Natl. Acad. Sci. USA 1994, 91, 8324-8328.
6. Delmotte, P.; Delmotte-Plaqu, J. A New Anitifungal Substance of Fungal Origin. Nature 1953, 1, 344.
7. McCapra, F.; Scott, A. I.; Delmotte, P.; Delmotte-Plaqu, J.; Bhacca, N. S. The Constitution of Monorden, an Antibiotic with Tranquilising Action. Tetrahedron Lett. 1964, 15, 869-875.
8. Mirrington, R. N.; Ritchie, E.; Shoppee, C. W.; Taylor, W. C.; Sternhell, S. The Constitution of Radicicol. Tetrahedron Lett. 1964, 7, 365-370.
9. Betina, V.; Micckova, D. Antimicrobial Properties of Fungal Macrolide Antibiotics. Z. Allg. Mikrobiol. 1972, 12, 355-364.
10. Betina, V.; Micckova, D. Morphogenetic Activity of Cytochalasins, Cyanein, and Monorden in Botrytis Cinerea. Z. Allg. Mikrobiol. 1973, 13, 287-298.
11. Horakova, K.; Betina, V. Cytotoxic Activity of Macrocyclic Metabolites from Fungi. Neoplasma 1977, 24, 21-27.
12. v-Src Protein Kinase Both in Vivo and in Vitro by Radicicol. Cancer Res. 1992, 52, 6926-6930.
13. Zhao, J. F.; Nakano, H.; Sharma, S. Suppression of Ras and Mos Transformation by Radicicol. Oncogene 1995, 11, 161-173.
14. Sharma, S. V.; Agatsuma, T.; Nakano, H. Targeting of the Protein Chaperone, Hsp90, by the Transformation Suppressing Agent, Radicicol. Oncogene 1998, 16, 2639-2645.
15. Sasaki, K.; Rinehart, K. L.; Jr.; Slomp, G.; Grostic, M. F.; Olson, E. C. Geldanamycin. I. Structure Assignment. J. Am. Chem. Soc. 1970, 92, 7591-7593.
16. Sasaki, K.; Yasuda, H.; Onodera, K. Growth Inhibition of Virus Transformed Cells in Vitro and Antitumor Activity in Vivo of Geldanamycin and Its Derivatives. J. Antibiot. (Tokyo) 1979, 32, 849-851.
17. Omura, S.; Iwai, Y.; Takahashi, Y.; Sadakane, N.; Nakagawa, A.; Oiwa, H. ; Hasegawa, Y.; Ikai, T. Herbimycin, a New Antibiotic Produced by a Strain of Streptomyces. J. Antibiol. (Tokyo) 1979, 32, 255-261.
18. Omura, S.; Miyano, K.; Nakagawa, A.; Sano, H.; Komiyama, K.; Umezawa, I. ; Shibata, K.; Satsumabayashi, S. Chemical Modification and Antitumor Activity of Herbimycin A. 8,9-Epoxide, 7,9-Cyclic Carbamate, and 17 or 19-Amino Derivatives. J. Antibiot. (Tokyo) 1984, 37, 1264-1267.
19. Shibata, K.; Satsumabayashi, S.; Sano, H.; Komiyama, K.; Nakagawa, A.; Omura, S. Chemical Modification of Herbimycin A. Synthesis and in Vivo Antitumor Activities of Halogenated and Other Related Derivatives of Herbimycin A. J. Antibiol. (Tokyo) 1986, 39, 415-423.
20. Tanida, S.; Hasegawa, T.; Higashide, E. Macbecins I and II, New Antitumor Antibiotics. I. Producing Organism, Fermentation and Antimicrobial Activities. J. Antibiol. (Tokyo) 1980, 33, 199-204.
21. Muroi, M.; Izawa, M.; Kosai, Y.; Asai, M. Macbecins I and II, New Antitumor Antibiotics. I. Isolation and Characterization. J. Antibiol. (Tokyo) 1980, 33, 205-212.
22. Duesberg, P. H. Activated Proto-One Genes: Sufficient or Necessary for Cancer? Science 1985, 228, 669-677.
23. Klein, G.; Klein, E. Evolution of Tumours and the Impact of Molecular Oncology. Nature 1985, 315, 190-195.
24. Chen, Y. C.; Hayman, M. J.; Vogt, P. K. Properties of Mammalian Cells Transformed by Temperature-Sensitive Mutants of Avian Sarcoma Virus. Cell 1977, 11, 513-521.
25. Jove, R.; Hanafusa, H. Cell Transformation by the Viral Src Oncogene. Annu. Rev. Cell Biol. 1987, 3, 31-56.
26. v-Src. Cancer Res. 1989, 49, 780-785.
27. Murakami, Y.; Mizuno, S.; Hori, M.; Uehara, Y. Reversal of Transformed Phenotypes by Herbimycin A in Src Oncogene Expressed Rat Fibroblasts. Cancer Res. 1988, 48, 1587-1590.
28. v-Src with the Cytoskeletal Structure and with Phosphatidylinositol 3 Kinase. Oncogene 1993, 8, 559-564.
29. Schulte, T. W.; Blagosklonny, M. V.; Ingui, C.; Neckers, L. Disruption of the Raf-1-Hsp90 Molecular Complex Results in Destabilization of Raf-1 and Loss of Raf-1-Ras Association. J. Biol. Chem. 1995, 270, 24585-24588.
30. Murakami, Y.; Mizuno, S.; Uehara, Y. Accelerated Degradation of 160 KDa Epidermal Growth Factor (EGF) Receptor Precursor by the Tyrosine Kinase Inhibitor Herbimycin A in the Endoplasmic Reticulum of A431 Human Epidermoid Carcinoma Cells. Biochem. J. 1994, 301, 63-68.
31. Sepp-Lorenzino, L.; Ma, Z.; Lebwohl, D. E.; Vinitsky, A.; Rosen, N. Herbimycin A Induces the 20 S Proteasome- and Ubiquitin-Dependent Degradation of Receptor Tyrosine Kinases. J. Biol. Chem. 1995, 270, 16580-16587.
32. 14C]Herbimycin A and Its Use in the Elucidation of the Kinase Inactivation Mechanism. FEBS Lett. 1994, 340, 155-158.
33. Fukazawa, H.; Li, P. M.; Yamamoto, C.; Murakami, Y.; Mizuno, S.; Uehara, Y. Specific Inhibition of Cytoplasmic Protein Tyrosine Kinases by Herbimycin A in Vitro. Biochem. Pharmacol. 1991, 42, 1661-1671.
34. Lck. J. Biol. Chem. 1993, 268, 17547-17553.
35. Senga, T.; Miyazaki, K.; Machida, K.; Iwata, H.; Matsuda, S.; Nakashima, I.; Hamaguchi, M. Clustered Cysteine Residues in the Kinase Domain of v-Src: Critical Role for Protein Stability, Cell Transformation and Sensitivity to Herbimycin A. Oncogene 2000, 19, 273-279.
36. Rowley, J. D. Letter: A New Consistent Chromosomal Abnormality in Chronic Myelogenous Leukaemia Identified by Quinacrine Fluorescence and Giemsa Staining. Nature 1973, 243, 290-293.
37. Yunis, J. J. The Chromosomal Basis of Human Neoplasia. Science 1983, 221, 227-236.
38. Knopka, J. B.; Watanabe, S. M.; Singer, J. W.; Collins, S. J.; Witte, O. N. Cell Lines and Clinical Isolates Derivative from Ph-1-Positive Chronic Myelogenous Leukemia Patients Express C-Abl Proteins with a Common Structural Alteraion. Proc. Natl. Acad. Sci. USA 1985, 82, 1810-1814.
39. Daley, G. Q.; Van Etten, R. A.; Baltimore, D. Induction of Chronic Myelogenous Leukemia in Mice by the P210bcr/abl Gene of the Philadelphia Chromosome. Science 1990, 247, 824-830.
40. Heisterkamp, N.; Jenster, G.; ten Hoeve, J.; Zovich, D.; Pattengale, P. K.; Groffen, J. Acute Leukaemia in Bcr/Abl Transgenic Mice. Nature 1990, 344, 251-253.
41. Uehara, Y.; Murakami, Y.; Mizuno, S.; Kawai, S. Inhibition of Transforming Activity of Tyrosine Kinase Oncogenes by Herbimycin A. Virology 1988, 164, 294-298.
42. Honma, Y.; Okabe-Kado, J.; Hozumi, M.; Uchara, Y.; Mizuno, S. Induction of Erythroid Differentiation of K562 Human Leukemic Cells by Herbimycin A, an Inhibitor of Tyrosine Kinase Activity. Cancer Res. 1989, 49, 331-334.
43. I-Positive Leukemia Cell Growth. Blood 1992, 80, 1330-1338.
44. Honma, Y.; Kasukabe, T.; Hozumi, M.; Shibata, K.; Omura, S. Effects of Herbimycin A Derivatives on Growth and Differentiation of K562 Human Leukemic Cells. Anticancer Res. 1992, 12, 189-192.
45. Okabe, M.; Uehara, Y.; Noshima, T.; Itaya, T.; Kunieda, Y.; Kurosawa, M. In Vivo Antitumor Activity of Herbimycin A, a Tyrosine Kinase Inhibitor, Targeted against Bcr/Abl Oncoprotein in Mice Bearing Bcr/Abl-Transfected Cells. Leuk. Res. 1994, 18, 867-873.
46. Honma, Y.; Matsuo, Y.; Hayashi, Y.; Omura, S. Treatment of Philadelphia-Chromosome-Positive Human Leukemia in Scid Mouse Model with Herbimycin A, Bcr-Abl Tyrosine Kinase Activity Inhibitor. Int. J. Cancer 1995, 60, 685-688.
47. Drummond, M. W.; Holyoake, T. L. Tyrosine Kinase Inhibitors in the Treatment of Chronic Myeloid Leukaemia: So Far So Good? Blood Rev. 2001, 15, 85-95.
48. crbB-2 in Vitro and in Vivo by Geldanamycin and Dihydrogeldanamycin Derivatives. J. Med Chem. 1995, 38, 3806-3812.
49. Schnur, R. C.; Corman, M. L.; Gallaschun, R. J.; Cooper, B. A.; Dee, M. F.; Doty, J. L.; Muzzi, M. L.; DiOrio, C. I.; Barbacci, E. G.; Miller, P. E.; Pollack, V. A.; Savage, D. M.; Sloan, D. E.; Pustilnik, L. R.; Moyer, J. D.; Moyer, M. P. ErbB-2 Oncogene
50. Inhibition by Geldanamycin Derivatives: Synthesis, Mechanism of Action, and Structure-Activity Relationships. J. Med. Chem. 1995, 38, 3813-3820.
51. Maloney, A.; Workman, P. Hsp90 as a New Therapeutic Target for Cancer Therapy: The Story Unfolds. Expert Opin. Biol. Ther. 2002, 2, 3-24.
52. Grabley, S.; Thiericke, R. Bioactive Agents from Natural Sources: Trends in Discovery and Application. Adv. Biochem. Eng. Biotechnol. 1999, 64, 101-154.
53. Harvey, A. Strategies for Discovering Drugs from Previously Unexplored Natural Products. Drug Discov. Today 2000, 5, 294-300.
54. Cragg, G. M.; Newman, D. J.; Snader, K. M. Natural Products in Drug Discovery and Development. J. Nat. Prod. 1997, 60, 52-60.
55. Henkel, T.; Brunne, R.; Muller, H.; Reiehel, F. Statisitical Investigation into the Structural Complimentarity of Natural Products and Synthetic Compounds. Angew. Chem. Int. Ed. Engl. 1999, 38, 643-647.