Differential effects of natural product microtubule stabilizers on microtubule assembly: Single agent and combination studies with Taxol, epothilone B, and discodermolide

ChemBioChem

Volumn 10, Issue 1, 2009, Pages 166-175

  Gertsch, Jürg ^a   Meier, Sarah ^a   Müller, Martin ^a   Altmann, Karl Heinz ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Discodermolide; Microtubule stabilizer; Microtubules; Natural products; Proteins

Indexed keywords

BETA TUBULIN; DISCODERMOLIDE; EPOTHILONE B; GUANOSINE TRIPHOSPHATE; NATURAL PRODUCT; PACLITAXEL; POLYMER; STABILIZING AGENT; ALKANE; BIOLOGICAL PRODUCT; CARBAMIC ACID DERIVATIVE; EPOTHILONE DERIVATIVE; LACTONE; PYRONE DERIVATIVE; TUBULIN; TUBULIN MODULATOR;

ANIMAL TISSUE; ARTICLE; CANCER INHIBITION; CONTROLLED STUDY; DRUG STABILITY; DRUG STRUCTURE; ELECTRON MICROSCOPY; MICROTUBULE ASSEMBLY; NONHUMAN; PHYSICAL STRESS; PRIORITY JOURNAL; PROTEIN LOCALIZATION; STRUCTURE ANALYSIS; ULTRASOUND; ANIMAL; BRAIN; CELL PROLIFERATION; CHEMISTRY; CYTOLOGY; DRUG COMBINATION; DRUG EFFECT; DRUG POTENTIATION; HUMAN; METABOLISM; MICROTUBULE; PHOTOMETRY; PROTEIN MULTIMERIZATION; PROTEIN QUATERNARY STRUCTURE; SWINE;

ALKANES; ANIMALS; BIOLOGICAL PRODUCTS; BRAIN; CARBAMATES; CELL PROLIFERATION; DRUG COMBINATIONS; DRUG SYNERGISM; EPOTHILONES; HUMANS; LACTONES; MICROSCOPY, ELECTRON; MICROTUBULES; NEPHELOMETRY AND TURBIDIMETRY; PACLITAXEL; PROTEIN MULTIMERIZATION; PROTEIN STRUCTURE, QUATERNARY; PYRONES; SWINE; TUBULIN; TUBULIN MODULATORS;

EID: 59649108112     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200800556     Document Type: Article

References (52)

1. For recent reviews on microtubule-stabilizing agents, see: a) K.-H. Altmann, J. Gertsch, Nat. Prod. Rep. 2007, 24, 327-357;
2. b) D. C. Myles, Annu. Rep. Med. Chem. 2002, 37, 125-132;
3. c) K.-H. Altmann, Curr. Opin. Chem. Biol. 2001, 5, 424-431.
4. For reviews on MT structure and function, see: a) M. A. Jordan, L. Wilson, Nat. Rev. Cancer 2004, 4, 253-265;
5. b) E. Nogales, Annu. Rev. Biophys. Biomol. Struct. 2001, 30, 397-420;
6. c) O. Valiron, N. Caudron, D. Job, Cell. Mol. Life Sci. 2001, 58, 2069-2084;
7. d) L. Amos, Org. Biomol. Chem. 2004, 2, 2153-2160.
8. M. A. Jordan, Curr. Med. Chem: Anti-Cancer Agents 2002, 2, 1-14.
9. a) Y. Zhai, P. J. Kronebusch, P. M. Simon, G. G. Borisy, J. Cell Biol. 1996, 135, 201-214;
10. b) N. M. Rusan, C. J. Fagerstrom, A.-M. C. Yvon, P. Wadsworth, Mol. Biol. Cell 2001, 12, 971-980.
11. a) J. Crown, M. O'Leary, W.-S. Ooi, Oncologist 2004, 9 (Suppl. 2), 24-32;
12. b) E. K. Rowinsky, Annu. Rev. Med. 1997, 48, 353-374.
13. M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon, A. T. McPhail, J. Am. Chem. Soc. 1971, 93, 2325-2327.
14. P. B. Schiff, J. Fant, S. B. Horwitz, Nature 1979, 277, 665-667.
15. For recent reviews on epothilones, see: a) K.-H. Altmann, B. Pfeiffer, S. Arseniyadis, B. A. Pratt, K. C. Nicolaou, ChemMedChem 2007, 2, 396-423;
16. b) G. Höfle, H. Reichenbach in Anticancer Agents from Natural Products (Eds.: G. M. Cragg, D. G. I. Kingston, D. J. Newman), CRC Press, Boca Raton, 2005, pp. 413-450.
17. For recent reviews on clinical trials with Epo B (EPO906, patupilone), see: a) M. Harrison, C. Swanton, Exp Opin. Investig. Drugs 2008, 17, 523-546;
18. b) J. M. G. Larkin, S. B. Kaye, Expert Opin. Invest. Drugs 2006, 15, 691-702.
19. According to company information, clinical trials with DDM were terminated by Novartis after phase I.
20. http://www.novartisoncology.com/page/patupilone.jsp.
21. Ixabepilone is marketed in the US by Bristol-Myers Squibb (BMS) under the trade name Ixempra®: E. Kaminskas, X. Jiang, R. Aziz, J. Bullock, R. Kasliwal, R. Harapanhalli, S. Pope, R. Sridhara, J. Leighton, B. Booth, R. Dagher, R. Justice, R. Pazdur, Clin. Cancer Res. 2008, 14, 4378-4384.
22. For leading references on ixabepilone, see: a) E. S. Thomas, H. L. Gomez, R. K. Li, H.-C. Chung, L. E. Fein, V. F. Chan, J. Jassem, X. B. Pivot, J. Klimovsky, F. Hurtado de Mendoza, B. Xu, M. Campone, G. L. Lerzo, R. A. Peck, P. Mukhopadhyay, L. T. Vahdat, H. H. Roche, J. Clin. Oncol. 2007, 25, 5210-5217;
23. b) F. Y. F. Lee, R. Borzilleri, C. R. Fairchild, S. H. Kim, B. H. Long, C. Reventos-Suarez, G. D. Vite, W. C. Rose, R. A. Kramer, Clin. Cancer Res. 2001, 7, 1429-1437;
24. c) R. M. Borzilleri, X. P. Zheng, R. J. Schmidt, J. A. Johnson, S. H. Kim, J. D. DiMarco, C. R. Fairchild, J. Z. Gougoutas, F. Y. F. Lee, B. H. Long, G. D. Vite, J. Am. Chem. Soc. 2000, 122, 8890-8897.
25. a) K.-H. Altmann, M. Wartmann, T. O'Reilly, Biochim. Biophys. Acta Rev. Cancer 2000, 1470, M79-M91;
26. b) R. J. Kowalski, P. Giannakakou, E. Hamel, J. Biol. Chem. 1997, 272, 2534-2541;
27. c) D. M. Bollag, P. A. McQueney, J. Zhu, O. Hensens, L. Koupal, J. Liesch, M. Goetz, E. Lazarides, C. M. Woods, Cancer Res. 1995, 55, 2325-2333.
28. a) L. A. Martello, H. M. McDaid, D. L. Regl, C. P. H. Yang, D. Meng, T. R. R. Pettus, M. D. Kaufman, H. Arimoto, S. J. Danishefsky, A. B. Smith III, S. B. Horwitz, Clin. Cancer Res. 2000, 6, 1978-1987;
29. b) E. ter Haar, R. J. Kowalski, E. Hamel, C. M. Lin, R. E. Longley, S. P. Gunasekara, H. S. Rosenkranz, B. W. Day, Biochemistry 1996, 35, 243-250.
30. G. S. Huang, L. Lopez-Barcons, B. S. Freeze, A. B. Smith III, G. L. Goldberg, S. B. Horwitz, H. M. McDaid, Clin. Cancer Res. 2006, 12, 298-304.
31. S. Honore, K. Kamath, D. Braguer, L. Wilson, C. Briand, M. A. Jordan, Mol. Cancer Ther. 2003, 2, 1303-1311.
32. R. M. Buey, I. Barasoain, E. Jackson, A. Meyer, P. Giannakakou, I. Paterson, S. Mooberry, J. M. Andreu, J. F. Diaz, Chem. Biol. 2005, 12, 1269-1279.
33. a) L. A. Martello, M. J. LaMarche, L. He, T. J. Beauchamp, A. B. Smith III, S. B. Horwitz, Chem. Biol. 2001, 8, 843-855;
34. b) R. J. Kowalski, P. Giannakakou, S. P. Gunasekera, R. E. Longley, B. W. Day, E. Hamel, Mol. Pharmacol. 1997, 52, 613-622.
35. P. Meurer-Grob, J. Kasparian, R. H. Wade, Biochemistry 2001, 40, 8000-8008.
36. E. J. Gapud, R. Bai, A. K. Ghosh, E. Hamel, Mol. Pharmacol. 2004, 66, 113-121.
37. D. E. Pryor, A. O'Brate, G. Bilcer, J. F. Diaz, Y. Wang, Y. Wang, M. Kabaki, M. K. Jung, J. M. Andreu, A. K. Ghosh, P. Giannakakou, E. Hamel, Biochemistry 2002, 41, 9109-9115.
38. Combinations of laulimalide or peloruside A (neither of which binds to the taxoid site on β-tubulin) with taxoid-site MSAs were recently evaluated for their effects on tubulin polymerization but not on MT morphology: a) A. Wilmes, K. Bargh, C. Kelly, P. T. Northcote, J. H. Miller, Mol. Pharm. 2007, 4, 269-280;
39. b) E. Hamel, B. W. Day, J. H. Miller, M. K. Jung, P. T. Northcote, A. K. Ghosh, D. P. Curran, M. Cushman, K. C. Nicolaou, I. Paterson, E. J. Sorensen, Mol. Pharmacol. 2006, 70, 1555-1564.
40. E. Hamel, A. A. del Campo, J. Lustbader, C. M. Lin, Biochemistry 1983, 22, 1271-1279.
41. C. M. Lin, Y. Q. Jiang, A. G. Chaudhary, J. M. Rimoldi, D. G. I. Kingston, E. Hamel, Cancer Chemother. Pharmacol. 1996, 38, 136-140.
42. D. T. Hung, J. Chen, S. L. Schreiber, Chem. Biol. 1996, 3, 287-293.
43. D. A. Dabydeen, G. J. Florence, I. Paterson, E. Hamel, Cancer Chemother. Pharmacol. 2004, 53, 397-403.
44. Q. Lu, R. F. Luduena, J. Biol. Chem. 1994, 269, 2041-2047;
45. b) Q. Lu, R. F. Luduena, Cell Struct. Funct. 1993, 18, 173-182;
46. c) A. Banerjee, M. C. Roach, P. Trcka, R. F. Luduena, J. Biol. Chem. 1990, 265, 1794-1799.
47. D. Panda, H. P. Miller, A. Banerjee, R. F. Luduena, L. Wilson, Proc. Natl. Acad. Sci. USA 1994, 91, 11358-11362.
48. V. Rezania, O. Azarenko, M. A. Jordan, H. Bolterauer, R. F. Luduena, J. T. Huzil, J. A. Tuszynski, Biophys. J. 2008, 95, 1993-2008.
49. F. Sasse, Curr. Biol. 2000, 10, R469.
50. C. Madiraju, M. C. Edler, E. Hamel, B. S. Raccor, S. Brianne, R. Van Balachandran, G. Zhu, K. A. Giuliano, A. Vogt, Y. Shin, J.-H. Fournier, Y. Fukui, A. M. Brückner, D. P. Curran, B. W. Day, Biochemistry 2005, 44, 15053-15063.
51. L. E. Klein, B. S. Freeze, A. B. Smith III, S. B. Horwitz, Cell Cycle 2005, 4, 501-507.
52. M. Castoldi, A. V. Popov, Protein Expression Purif. 2003, 32, 83-88.