Semisynthesis and degradation of the tubulin inhibitors epothilone and tubulysin

Pure and Applied Chemistry

Volumn 75, Issue 2-3, 2003, Pages 167-178

  Hofle G ^a   Glaser, N ^a   Leibold, T ^a   Karama, U ^a   Sasse, F ^a   Steinmetz, H ^a  

^a HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

12,13 SECO EPOTHILONE C; ALKENE; ANTINEOPLASTIC AGENT; BMS 247750; BMS 310705; DOLASTATIN 10; EPOTHILONE; EPOTHILONE A; EPOTHILONE B; EPOTHILONE B AMINE; EPOTHILONE B LACTAM; EPOTHILONE C; EPOTHILONE F; ESTERASE; ETHYLENE; FORMALDEHYDE; ISOLEUCINE; ISOVALERIC ACID; METHYL GROUP; OXIDE; PACLITAXEL; PHENYLALANINE DERIVATIVE; PIPECOLIC ACID DERIVATIVE; TETRAPEPTIDE; THIAZOLE DERIVATIVE; TUBULYSIN; TUBULYSIN D; UNCLASSIFIED DRUG; VALINE; VINBLASTINE;

CHEMICAL MODIFICATION; CLINICAL TRIAL; CONFERENCE PAPER; CYTOTOXICITY; DRUG CONFORMATION; DRUG DEGRADATION; DRUG STABILITY; DRUG SYNTHESIS; EPOXIDATION; HUMAN; HYDROLYSIS; HYDROXYLATION; MYXOCOCCALES; NONHUMAN; OXIDATION; PRIORITY JOURNAL; RING CLOSING METATHESIS; RING OPENING; STANDARD; STRUCTURE ACTIVITY RELATION;

EID: 0037318023     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200375020167     Document Type: Conference Paper

References (56)

1. For reviews, see: A. Jordan, J. A. Hadfield, N. J. Lawrence, A. T. McGown. Med. Res. Rev. 18, 259-296 (1998); M. A. Jordan. Curr. Med. Chem.-Anti-Cancer Agents 2, 1-17 (2002).
2. For reviews, see: A. Jordan, J. A. Hadfield, N. J. Lawrence, A. T. McGown. Med. Res. Rev. 18, 259-296 (1998); M. A. Jordan. Curr. Med. Chem.-Anti-Cancer Agents 2, 1-17 (2002).
3. For a review, see: E. Hamel. Med. Res. Rev. 207-231 (1996).
4. S. L. Mooberry, T. G. Hernandez, A. Plubrukarn, B. S, Davidson. Cancer Res. 59, 653-660 (1999); B. Sato, H. Muramatsu, M. Miyanchi, Y. Hori, S. Takase, M. Hino, S. Hashimoto, H. Terano. J. Antibiot. 53, 123-130 (2000).
5. S. L. Mooberry, T. G. Hernandez, A. Plubrukarn, B. S, Davidson. Cancer Res. 59, 653-660 (1999); B. Sato, H. Muramatsu, M. Miyanchi, Y. Hori, S. Takase, M. Hino, S. Hashimoto, H. Terano. J. Antibiot. 53, 123-130 (2000).
6. G. Höfle, N. Bedorf, K. Gerth, H. Reichenbach. (GBF) DE-4138042 (1993); Chem. Abstr. 120, 52841 (1993); G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth, H. Reichenbach. Angew. Chem. 108, 1671-1673 (1996); Angew. Chem., Int. Ed. 35, 1567-1569 (1996); K. Gerth, N. Bedorf, G. Höfle, H. Irschik, H. Reichenbach. J. Antibiot. 49, 560-563 (1996).
7. G. Höfle, N. Bedorf, K. Gerth, H. Reichenbach. (GBF) DE-4138042 (1993); Chem. Abstr. 120, 52841 (1993); G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth, H. Reichenbach. Angew. Chem. 108, 1671-1673 (1996); Angew. Chem., Int. Ed. 35, 1567-1569 (1996); K. Gerth, N. Bedorf, G. Höfle, H. Irschik, H. Reichenbach. J. Antibiot. 49, 560-563 (1996).
8. G. Höfle, N. Bedorf, K. Gerth, H. Reichenbach. (GBF) DE-4138042 (1993); Chem. Abstr. 120, 52841 (1993); G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth, H. Reichenbach. Angew. Chem. 108, 1671-1673 (1996); Angew. Chem., Int. Ed. 35, 1567-1569 (1996); K. Gerth, N. Bedorf, G. Höfle, H. Irschik, H. Reichenbach. J. Antibiot. 49, 560-563 (1996).
9. G. Höfle, N. Bedorf, K. Gerth, H. Reichenbach. (GBF) DE-4138042 (1993); Chem. Abstr. 120, 52841 (1993); G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth, H. Reichenbach. Angew. Chem. 108, 1671-1673 (1996); Angew. Chem., Int. Ed. 35, 1567-1569 (1996); K. Gerth, N. Bedorf, G. Höfle, H. Irschik, H. Reichenbach. J. Antibiot. 49, 560-563 (1996).
10. G. Höfle, N. Bedorf, K. Gerth, H. Reichenbach. (GBF) DE-4138042 (1993); Chem. Abstr. 120, 52841 (1993); G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth, H. Reichenbach. Angew. Chem. 108, 1671-1673 (1996); Angew. Chem., Int. Ed. 35, 1567-1569 (1996); K. Gerth, N. Bedorf, G. Höfle, H. Irschik, H. Reichenbach. J. Antibiot. 49, 560-563 (1996).
11. D. M. Bollag, P. A. McQueney, J. Zhu, O. Hensens, L. Koupal, J. Liesch, M. Goetz, E. Lazarides, C. M. Woods. Cancer Res. 55, 2325-2333 (1995).
12. F. Sasse, H. Steinmetz, J. Heil, G. Höfle, J. Antibiot. 53, 879-885 (2000).
13. H. Irschik, R. Jansen, K. Gerth, G. Höfle, H. Reichenbach. J. Antibiot. 48, 31-35 (1995).
14. R. J. Kowalski, P. Giannakakou, E. Hamel. J. Biol. Chem. 272, 2534-2541 (1997).
15. For reviews, see: K. C. Nicolaou, F. Roschangar, D. Vourloumis. Angew. Chem. 110, 2120-2153 (1998); Angew. Chem., Int. Ed. 37, 2014-2045 (1998); J. Mulzer. Monatsh. Chem. 131, 205-238 (2000); K.-A. Altmann, G. Bold, G. Caravatti, N. End, A. Försheimer, V. Guagnano, T. O'Reilly, M. Wartmann. Chimia 54, 612-621 (2000); K. C. Nicolaou, A. Ritzen, K. Namoto. Chem. Commun. 1523-1535 (2001).
16. For reviews, see: K. C. Nicolaou, F. Roschangar, D. Vourloumis. Angew. Chem. 110, 2120-2153 (1998); Angew. Chem., Int. Ed. 37, 2014-2045 (1998); J. Mulzer. Monatsh. Chem. 131, 205-238 (2000); K.-A. Altmann, G. Bold, G. Caravatti, N. End, A. Försheimer, V. Guagnano, T. O'Reilly, M. Wartmann. Chimia 54, 612-621 (2000); K. C. Nicolaou, A. Ritzen, K. Namoto. Chem. Commun. 1523-1535 (2001).
17. For reviews, see: K. C. Nicolaou, F. Roschangar, D. Vourloumis. Angew. Chem. 110, 2120-2153 (1998); Angew. Chem., Int. Ed. 37, 2014-2045 (1998); J. Mulzer. Monatsh. Chem. 131, 205-238 (2000); K.-A. Altmann, G. Bold, G. Caravatti, N. End, A. Försheimer, V. Guagnano, T. O'Reilly, M. Wartmann. Chimia 54, 612-621 (2000); K. C. Nicolaou, A. Ritzen, K. Namoto. Chem. Commun. 1523-1535 (2001).
18. For reviews, see: K. C. Nicolaou, F. Roschangar, D. Vourloumis. Angew. Chem. 110, 2120-2153 (1998); Angew. Chem., Int. Ed. 37, 2014-2045 (1998); J. Mulzer. Monatsh. Chem. 131, 205-238 (2000); K.-A. Altmann, G. Bold, G. Caravatti, N. End, A. Försheimer, V. Guagnano, T. O'Reilly, M. Wartmann. Chimia 54, 612-621 (2000); K. C. Nicolaou, A. Ritzen, K. Namoto. Chem. Commun. 1523-1535 (2001).
19. For reviews, see: K. C. Nicolaou, F. Roschangar, D. Vourloumis. Angew. Chem. 110, 2120-2153 (1998); Angew. Chem., Int. Ed. 37, 2014-2045 (1998); J. Mulzer. Monatsh. Chem. 131, 205-238 (2000); K.-A. Altmann, G. Bold, G. Caravatti, N. End, A. Försheimer, V. Guagnano, T. O'Reilly, M. Wartmann. Chimia 54, 612-621 (2000); K. C. Nicolaou, A. Ritzen, K. Namoto. Chem. Commun. 1523-1535 (2001).
20. (a) M. Sefkow, M. Kiffe, D. Schummer, G. Höfle, Bioorg. Med. Chem. Lett. 8, 3025-3030 (1998);
21. (b) M. Sefkow, M. Kiffe, G. Höfle. Bioorg. Med. Chem. Lett. 8, 3031-3036 (1998);
22. (c) M. Sefkow and G. Höfle. Heterocycles 48, 2485-2488 (1998);
23. (d) G. Höfle, N. Glaser, M. Kiffe, H.-J. Hecht, F. Sasse, H. Reichenbach. Angew. Chem. 111, 2090-2093 (1999); Angew. Chem., Int. Ed. 38, 1971-1974 (1999);
24. (d) G. Höfle, N. Glaser, M. Kiffe, H.-J. Hecht, F. Sasse, H. Reichenbach. Angew. Chem. 111, 2090-2093 (1999); Angew. Chem., Int. Ed. 38, 1971-1974 (1999);
25. (e) G. Höfle, N. Glaser, T. Leibold, M. Sefkow. Pure Appl. Chem. 71, 2019-2024 (2000);
26. (f) J. Johnson, S.-H. Kim, M. Bifano, J. DiMarco, C. Fairchild, J. Gougoutas, F. Lee, B. Long, J. Tokarski, G. Vite. Org. Lett. 2 (11), 1537-1540 (2000);
27. (g) R. M. Borzilleri, X. 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. 122, 8890-8897 (2000);
28. (h) A. Regueiro-Ren, R. M. Borzilleri, X. Zheng, S.-H. Kim, J. A. Johnson, C. R. Fairchild, F. Y. F. Lee, B. H. Long, G. D. Vite. Org. Lett. 3 (17), 2693-2696 (2001);
29. (i) Bristol-Myers Squibb, U.S. Patent No. 6,399,638 B1 (2002).
30. M.-W. M. Khalil, Doctoral Thesis, Technical University Braunschweig (1999).
31. I. H. Hardt, H. Steinmetz, K. Gerth, F. Sasse, H. Reichenbach, G. Höfle. J Nat. Prod. 64, 847-856 (2001).
32. U. Klar, W. Skuballa, B. Buchmann, W. Schwede, T. Bunte, J. Hoffmann, R. B. Lichtner. Am. Chem. Soc. Chap. 8, 131-146 (2001).
33. D.-S. Su, A. Balog, D. Meng, P. Bertinato, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He, S. B. Horwitz. Angew. Chem. 109, 2178-2180 (1997); Angew. Chem., Int. Ed. Engl. 36, 2093-2096 (1997); Pat. Epo D.
34. D.-S. Su, A. Balog, D. Meng, P. Bertinato, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He, S. B. Horwitz. Angew. Chem. 109, 2178-2180 (1997); Angew. Chem., Int. Ed. Engl. 36, 2093-2096 (1997); Pat. Epo D.
35. K. C. Nicolaou, D. Vourloumis, T. Li, J. Pastor, N. Winssinger, Y. He, S. Ninkovic, F. Sarabia, H. Vallberg, F. Roschangar, N. P. King, M. R. V. Finlay, P. Giannakakou, P. Verdier-Pinard, E. Hamel. Angew. Chem. 109, 2181-2187 (1997); Angew. Chem., Int. Ed. Engl. 36, 2097-2103 (1997).
36. K. C. Nicolaou, D. Vourloumis, T. Li, J. Pastor, N. Winssinger, Y. He, S. Ninkovic, F. Sarabia, H. Vallberg, F. Roschangar, N. P. King, M. R. V. Finlay, P. Giannakakou, P. Verdier-Pinard, E. Hamel. Angew. Chem. 109, 2181-2187 (1997); Angew. Chem., Int. Ed. Engl. 36, 2097-2103 (1997).
37. U. Karama and G. Höfle, Eur. J. Org. Chem. 1042-1049 (2003).
38. A. Flörsheimer and K.-H. Altmann. Monthly Focus: Oncologic, Endocrine & Metabolic, Expert Opin. Ther. Patents 11, 951-968 (2001) and references cited therein.
39. K. C. Nicolaou, D. Hepworth, N. P. King, M. Raymond, V. Finlay, R. Scarpelli, M. Manuela, A. Pereira, B. Bollbuck, A. Bigot, B. Werschkun, N. Winssinger. Chem. Eur. J. 6 (15), 2783-2800 (2000).
40. N. Glaser, Doctoral Thesis, Technical University Braunschweig (2001).
41. K. Gerth, H. Steinmetz, G. Höfle, H. Reichenbach. J. Antibiot. 55 (1), 41-45 (2002); Gesellschaft für Biotechnologische Forschung mbH, WO 98/22461 (1998).
42. K. Gerth, H. Steinmetz, G. Höfle, H. Reichenbach. J. Antibiot. 55 (1), 41-45 (2002); Gesellschaft für Biotechnologische Forschung mbH, WO 98/22461 (1998).
43. Bristol-Myers Squibb, WO 00/39276 (2000).
44. st, MEDI-196 (2002).
45. st, MEDI-196 (2002).
46. R. M. Borzilleri and G. D. Vite. Drugs of the Future 27, 1149-1163 (2003).
47. G. E. Keck, K. H. Tarbet, L. S. Geraci. J. Am. Chem. Soc. 115, 8467-8468 (1993).
48. K. C. Nicolaou, Y. He, D. Vourloumis, H. Vallberg, F. Roschangar, F. Sarabia, S. Ninkovic, Z. Yang, J. I. Trujillo. J. Am. Chem. Soc. 119, 7960-7973 (1997).
49. D. Schinzer, A. Limberg, A. Bauer, O. M. Böhm, M. Cordes. Angew. Chem. 109, 543-544 (1997); Angew. Chem., Int. Ed. 36, 523-524 (1997); D. Schinzer, A. Bauer, O. M. Böhm, A. Limgerg, M. Cordes. Chem. Eur. J. 5, 2483-2491 (1999).
50. D. Schinzer, A. Limberg, A. Bauer, O. M. Böhm, M. Cordes. Angew. Chem. 109, 543-544 (1997); Angew. Chem., Int. Ed. 36, 523-524 (1997); D. Schinzer, A. Bauer, O. M. Böhm, A. Limgerg, M. Cordes. Chem. Eur. J. 5, 2483-2491 (1999).
51. D. Schinzer, A. Limberg, A. Bauer, O. M. Böhm, M. Cordes. Angew. Chem. 109, 543-544 (1997); Angew. Chem., Int. Ed. 36, 523-524 (1997); D. Schinzer, A. Bauer, O. M. Böhm, A. Limgerg, M. Cordes. Chem. Eur. J. 5, 2483-2491 (1999).
52. G. Höfle. In GBF Annual Report, J.-H. Walsdorff (Ed.), pp. 103-107 (1998).
53. (a) G. R. Pettit, Y. Kamano, C. L. Herald, Y. Fujii, H. Kizu, M. R. Boyd, F. E. Boettner, D. L. Doubek, J. M. Schmidt, J.-C. Chapuis, C. Michel. Tetrahedron 49, 9151-9179 (1993);
54. (a) G. R. Pettit. In Progress in the Chemistry of Organic Natural Products, W. Herz, G. W. Kirby, R. E. Moore, W. Steglich, Ch. Tamm (Eds.), Vol. 70, pp. 1-79, Springer-Verlag, New York (1997).
55. R. Bai, S. J. Friedman, G. R. Pettit, E. Hamel. Biochem. Pharmacol. 43, 2637 (1992).
56. H. Luesch, R. E. Moore, V. J. Paul, S. L. Mooberry, T. H. Corbett. J. Nat. Prod. 64, 907-910 (2001).