Structure Determination, Conformational Analysis, Chemical Stability Studies, and Antitumor Evaluation of the Cryptophycins. Isolation of 18 New Analogs from Nostoc sp. Strain GSV 224

Journal of the American Chemical Society

Volumn 117, Issue 49, 1995, Pages 12030-12049

  Golakoti, Trimurtulu ^a   Ogino, Junichi ^a   Heltzel, Carl E ^a   Husebo, Trang Le ^a   Jensen, Craig M ^a   Larsen, Linda K ^a   Patterson, Gregory M L ^a   Moore, Richard E ^a   Mooberry, Susan L ^a   Corbett, Thomas H ^b   Valeriote, Frederick A ^b  

^a UNIVERSITY OF HAWAII CANCER CENTER   (United States)

^b WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CRYPTOPHYCIN; DEPSIPEPTIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL MODEL; ARTICLE; CELL DEATH; CHIRALITY; CONTROLLED STUDY; CRYSTALLOGRAPHY; CYANOBACTERIUM; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; INTRAVENOUS DRUG ADMINISTRATION; MASS SPECTROMETRY; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; TUMOR CELL;

EID: 0041537280     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00154a002     Document Type: Article

References (55)

1. Schwartz, R. E.; Hirsch, C. F.; Sesin, D. F.; Flor, J. E.; Chartrain, M.; Fromtling, R. E.; Harris, G. H.; Salvatore, M. J.; Liesch, J. M.; Yudin, K. J. Ind. Microbiol. 1990, 5, 113–24.
2. Hirsch, C. F.; Liesch, J. M.; Salvatore, M. J.; Schwartz, R. E.; Sesin, D. F. U. S. Patent 4, 946, 835, issued Aug 7, 1990.
3. Sesin, D. F. U. S. Patent 4, 868, 208, issued July 4, 1989.
4. Trimurtulu, G.; Ohtani, I.; Patterson, G. M. L.; Moore, R. E.; Corbett, T. H.; Valeriote, F. A.; Demchik, L. J. Am. Chem. Soc. 1994, 116, 4729–37.
5. Corbett, T. H.; Valeriote, F. A.; Polin, L.; Panchapor, C.; Pugh, S.; White, K.; Lowichik, N.; Knight, J.; Bissery, M.-C.; Wozniak, A.; LoRusso, P.; Biernat, L.; Polin, D.; Knight, L.; Biggar, S.; Looney, D.; Demchik, L.; Jones, J.; Jones, L.; Blair, S.; Palmer, K.; Essenmacher, S.; Lisow, L.; Mattes, K. C.; Cavanaugh, P. F.; Rake, J. B.; Baker, L. In Cytotoxic Anticancer Drugs: Models and Concepts for Drug Discovery and Development; Valeriote, F. A., Corbett, T. H., and Baker, L. H., Eds.; Kluwer Academic Publishers: Norwell, 1992; pp 35–87.
6. Valeriote, F. A.; Moore, R. E.; Patterson, G. M. L.; Paul, V. J.; Scheuer, P. J.; Corbett, T. In Anticancer Drug Discovery and Development: Natural Products and New Molecular Models; Valeriote, F. A., Corbett, T. H., and Baker, L. H., Eds.; Kluwer Academic Publishers: Norwell, 1994; pp 1–25.
7. Smith, C. D.; Zhang, X.; Mooberry, S. L.; Patterson, G. M. L.; Moore, R. E. Cancer Res. 1994, 54, 3779–84.
8. Barrow, R. A.; Hemscheidt, T.; Liang, J.; Paik, S.; Moore, R. E.; Tius, M. A. J. Am. Chem. Soc. 1995, 117, 2479–90.
9. Heltzel, C. E.; Ogino, J.; Golakoti, T.; Patterson, G. M. L.; Moore, R. E.; Larsen, L. K.; Mooberry, S. L.; Corbett, T. H.; Valeriote, F. A. manuscript in preparation.
10. Guroff, G. Biochem. Biophys. Res. Commun. 1966, 25, 622–8.
11. Kakimoto, Y.; Armsrong, M. D. J. Biol. Chem. 1961, 236, 3283–6.
12. Pollock, G. Anal. Biochem. 1974, 57, 82–88.
13. Fuganti, C.; Ghiringhelli, D. Gazz. Chim. Ital. 1969, 99, 316–22.
14. Mori, K. Tetrahedron 1976, 32, 1101–6.
15. Bergmann, M.; Zervas, L. Biochem. Z. 1928, 203, 280.
16. Greenstein, J. P.; Winitz, M. Chemistry of the Amino Acids; Wiley: New York, 1961: Vol. 3, p 2364.
17. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512–9.
18. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092–6.
19. Kusumi, T.; Fukushima, T.; Ohtani, I.; Kakisawa, H. Tetrahedron Lett. 1991, 32, 2939–42.
20. Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945–8.
21. Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511–5.
22. Marshall, J. A.; Crute, T. D., III; Hsi, J. D. J. Org. Chem. 1992, 57, 115–23.
23. Nelson, F. C.; Stachel, S. J.; Mattes, J. F. Tetrahedron Lett. 1994, 41, 7557–60.
24. Hanessian, S.; Meng, Q.; Oliver, E. Tetrahedron Lett. 1994, 35, 5393–96.
25. Marfey, P. Carlsberg Res. Commun. 1984, 49, 591–6.
26. Frank, H.; Nicholson, G. J.; Bayer, E. J. Chromatogr. Sci. 1977, 15, 174–6.
27. Gunther, K. J. Chromatogr. 1988, 448, 11–30.
28. RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986–97.
29. Kobayashi, M.; Aoki, S.; Ohyabu, N.; Kurosu, M.; Wang, W.; Kitagawa, I. Tetrahedron Lett., 1994, 35, 7969–72.
30. Kobayashi, M.; Aoki, S.; Ohyabu, N.; Kurosu, M.; Wang, W.; Kitagawa, I. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu (Abstracts of Symposium on the Chemistry of Natural Products, Hiroshima) 1994, 36, 744–751.
31. Kobayashi, M.; Kurosu, M.; Ohyabu, N.; Wang, W.; Fujii, S.; Kitagawa, I. Chem. Pharm. Bull. 1994, 42, 2196–8.
32. Kobayashi, M.; Kurosu, M.; Wang, W.; Kitagawa, I. Chem. Pharm. Bull. 1994, 42, 2394–6.
33. Faulkner, D. J.; He, H.-Y.; Unson, M. D.; Bewley, C. A. Gazz. Chim. Ital. 1993, 123, 301–308.
34. Unson, M. D.; Faulkner, D. J. Experientia 1993, 49, 349–353.
35. Unson, M. D.; Rose, C. B.; Faulkner, D. J.; Brinen, L. S.; Steiner, J. R.; Clardy, J. J. Org. Chem. 1993, 58, 6336–6343.
36. Winitz, M.; Bloch-Frankenthal, L.; Izumiya, N.; Birnbaum, S. M.; Baker, C. G.; Greenstein, J. P. J. Am. Chem. Soc. 1956, 78, 2423–30.
37. Baker, C. G.; Meister, A. J. Am. Chem. Soc. 1951, 73, 1336.
38. Radom, L.; Schleyer, P. R.; Pople, J. A. Ab Initio Molecular Orbital Theory: Wiley-Interscience: New York, 1986; pp 268–9.
39. Corbett, T. H.; Valeriote, F. A.; Demchik, L.; Polin, L.; Panchapor, C.; Pugh, S.; White, K.; Knight, J.; Jones, J.; Jones, L.; Foster, B.; Wiegand, R. A.; Lisow, L.; Golakoti, T.; Heltzel, C. E.; Ogino, J.; Patterson, G. M. L.; Moore, R. E. J. Exp. Ther. Oncol., in press.
40. Wyllie, A. H. Br. J. Cancer 1993, 67, 205–8.
41. Kerr, J. F. R.: Winterford, C. M.; Harmon, B. V. Cancer 1994, 73, 2013–26.
42. Ormerod, M. G.; O’Neill, C. F.; Robertson, D.; Harrap, K. R. Exp. Cell Res. 1994, 211, 231–7.
43. Mizumoto, K.; Rothman, R. J.; Farber, J. L. Mol. Pharm. 1994, 46, 890–5.
44. Bhalla, K.; Ibrado, A. M.; Tourkina, E.: Tang, C.; Mahoney, M. E.; Huang, Y. Leukemia 1993, 7, 563–8.
45. Piantini, U.; Sorensen, O. W.; Ernst, R. R. J. Am. Chem. Soc. 1982, 104, 6800–1.
46. Muller, N.; Ernst, R. R.; Wuthrich, K. J. Am. Chem. Soc. 1986, 108, 6482–92.
47. Bothner-By, A. A.; Stephens, R. L.; Lee, J.; Warren, C. D.; Jeanloz, R. W. J. Am. Chem. Soc. 1984, 106, 811–3.
48. Bax, A. J. Magn. Reson. 1985, 63, 207–13.
49. Bax, A.; Subramanian, S. J. Magn. Reson. 1986, 67, 565–9.
50. Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093–4.
51. Bax, A. J. Magn. Reson. 1984, 57, 314–8.
52. Rippka, R.; Deruelles, J.; Waterbury, J. B.; Herdman, M.; Stanier, R. Y. J. Gen. Microbiol. 1979, 111, 1–61.
53. Griffith, O. W.; Campbell, E. B.; Pirkle, W. H.; Tsipouras, A.; Hyun, M. H. J. Chromatogr. 1986, 362, 345–52.
54. Nagai, H.; Torigoe, K.; Satake, M.; Murata, M.; Yasumoto, T.; Hirota, H. J. Am. Chem. Soc. 1992, 114, 1102–3
55. Nakamura, H.; Asari, T.; Murai, A.; Kondo, T.; Yoshida, K.; Ohizumi, Y. J. Org. Chem. 1993, 58, 313–4.