A common pharmacophore for cytotoxic natural products that stabilize microtubules

Proceedings of the National Academy of Sciences of the United States of America

Volumn 96, Issue 8, 1999, Pages 4256-4261

  Ojima, Iwao ^a   Chakravarty, Subrata ^a   Inoue, Tadashi ^a   Lin, Songnian ^a   He, Lifeng ^b   Horwitz, Susan Band ^b   Kuduk, Scott D ^c   Danishefsky, Samuel J ^c  

^a STONY BROOK UNIVERSITY   (United States)

^b ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

^c MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISCODERMOLIDE; ELEUTHEROBIN; EPOTHILONE A; EPOTHILONE B; NATURAL PRODUCT; PACLITAXEL; UNCLASSIFIED DRUG;

ARTICLE; CANCER CHEMOTHERAPY; CYTOTOXICITY; DRUG BINDING; DRUG BINDING SITE; MICROTUBULE; MITOSIS INHIBITION; MOLECULAR MODEL; PHARMACOPHORE; POLYMERIZATION; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALKALOIDS; ALKANES; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CARBAMATES; COMPUTER GRAPHICS; DITERPENES; EPOTHILONES; EPOXY COMPOUNDS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MICROTUBULES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PACLITAXEL; PYRONES; THIAZOLES;

EID: 0033551046     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.96.8.4256     Document Type: Article

References (30)

1. Rowinsky, E. K., Cazenave, L. C. & Donehower, R. C. (1990) J. Natl. Cancer Inst. 82, 1247-1259.
2. Suffness, M. (1995) Taxol: Science and Applications (CRC, Boca Raton, FL).
3. Georg, G. I., Chen, T. T., Ojima, I. & Vyas, D. M. (1995) Taxane Anticancer Agents: Basic Science and Current Status (Am. Chem. Soc., Washington, DC).
4. Ojima, I., Kuduk, S. D. & Chakravarty, S. (1998) Adv. Med. Chem. 4, 69-124.
5. Ojima, I., Slater, J. C., Michaud, E., Kuduk, S. D., Bounaud, P.-Y., Vrignaud, P., Bissery, M.-C., Veith, J., Fera, P. & Bernacki, R. J. (1996) J. Med. Chem. 39, 3889-3896.
6. Ojima, I., Slater, J. S., Kuduk, S. D., Takeuchi, C. S., Gimi, R. H., Sun, C-M., Park, Y. H., Pera, P., Veith, J. M. & Bernacki, R. J. (1997) J. Med. Chem. 40, 267-278.
7. Ojima, I., Kuduk, S. D., Pera, P., Veith, J. M. & Bernacki, R. J. (1997) J. Med. Chem. 40, 279-285.
8. Shiff, P. B., Fant, J. & Horwitz, S. B. (1979) Nature (London) 277, 665-667.
9. Jordan, M. A., Toso, R. J. & Wilson, L. (1993) Proc. Natl. Acad. Sci. USA 90, 9552-9556.
10. Bollag, D. M., McQueney, P. A., Zhu, J., Hensens, O., Koupal, L., Liesch, J., Goetz, M., Lazarides, E. & Woods, C. M. (1995) Cancer Res. 55, 2325-2333.
11. Kowalski, R. J., Giannakakou, P. & Hamel, E. (1997) J. Biol. Chem. 272, 2534-2541.
12. Lindel, T., Jensen, P. R., Fenical, W., Long, B. H., Casazza, A. M., Carboni, J. & Fairchild, C. R. (1997) J. Am. Chem. Soc. 119, 8744-8745.
13. ter Haar, E., Kowalski, R. J., Hamel, E., Lin, C. M., Longley, R. E., Gunasekera, S. P., Rosenkranz, H. S. & Day, B. W. (1996) Biochemistry 35, 243-250.
14. Kowalski, R. J., Giannakakou, P., Gunasekera, S. P., Longley, R. E., Day, B. W. & Hamel, E. (1997) Mol. Pharmacol. 52, 613-622.
15. Giannakakou, P., Sackett, D. L., Kang, Y., Zhan, Z., Buters, J. T. M., Fojo, T. & Poruchynsky, M. S. (1997) J. Biol. Chem. 272, 17118-17125.
16. Kowalski, R. J., ter Haar, E., Longley, R. E., Gunasekera, S. P., Lin, C. M., Day, B. W. & Hamel, E. (1995) Mol. Biol. Cell 6, 368a.
17. Hung, D. T., Chen, J. & Schreiber, S. L. (1996) Chem. Biol. 3, 287-293.
18. Winkler, J. D. & Axelsen, P. H. (1996) Bioorg. Med. Chem. Lett. 6, 2963-2966.
19. Ojima, I., Lin, S., Chakravarty, S., Fenoglio, I., Park, Y. H., Sun, C., Appendino, G., Pera, P., Veith, J. M. & Bernacki, R. J. (1998) J. Org. Chem. 63, 1637-1645.
20. Vander Velde, D. G., Georg, G. I., Grunewald, G. L., Gunn, C. W. & Mitscher, L. A. (1993) J. Am. Chem. Soc. 115, 11650-11651.
21. Williams, H. J., Scott, A. I., Dieden, R. A., Swindell, C. S., Chirlian, L. E., Francl, M. M., Heerding, J. M. & Krauss, N. E. (1994) Can. J. Chem. 252-260.
22. Mastropaolo, D., Camerman, A., Luo, Y., Brayer, G. D. & Camerman, N. (1995) Proc. Natl. Acad. Sci. USA 92, 6920-6924.
23. Ojima, I., Kuduk, S. D., Chakravarty, S., Ourevitch, M. & Bégué, J.-P. (1997) J. Am. Chem. Soc. 119, 5519-5527.
24. Su, D., Balog, A., Meng, D., Bertinato, P., Danishefsky, S. J., Zheng, Y., Chou, T., He, L. & Horwitz, S. B. (1997) Angew. Chem. Int. Ed. Engl. 36, 2093-2096.
25. Chou, T., Zhang, X., Balog, A., Su, D., Meng, D., Savin, K., Bertino, J. R. & Danishefsky, S. J. (1998) Proc. Natl. Acad. Sci. USA 95, 9642-9647.
26. Chou, T. C., Zhang, X. G., Harris, C. R., Kuduk, S. D., Balog, A., Savin, K. & Danishefsky, S. J. (1998) Proc. Natl. Acad. Sci USA 95, 15798-15802.
27. McDaid, H. M., Bhattacharya, S. K., Chen, S., He, L., Shen, H., Gutteridge, C. E., Horwitz, S. B. & Danishefsky, S. J. (1999) Cancer Chemother. Pharmacol., in press.
28. Nicolaou, K. C., Kim, S., Pfefferkorn, J., Xu, J., Ohshima, T., Hosokawa, S., Vourloumis, D. & Li, T. (1998) Angew. Chem. Int. Ed. Engl. 37, 1418-1421.
29. Nogales, E., Wolf, S. G. & Downing, K. H. (1998) Nature (London) 391, 199-203.
30. Höfle, G., Bedorf, N., Steinmetz, H., Schomburg, D., Gerth, K. & Reichenbach, H. (1996) Angew. Chem. Int. Ed. Engl. 35, 1567-1569.