A common pharmacophore for taxol and the epothilones based on the biological activity of a taxane molecule lacking a C-13 side chain

Biochemistry

Volumn 39, Issue 14, 2000, Pages 3972-3978

  He, Lifeng ^a   Jagtap, Prakash G ^b   Kingston, David G I ^b   Shen, Heng Jia ^a   Orr, George A ^a   Horwitz, Susan Band ^a  

^a ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

^b VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACCATIN III; EPOTHILONE A; EPOTHILONE B; PACLITAXEL;

ARTICLE; CANCER CELL; CELL PROLIFERATION; DRUG BINDING; DRUG STRUCTURE; MOLECULAR MODEL; PHARMACOPHORE; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; BRIDGED COMPOUNDS; HUMANS; MODELS, MOLECULAR; PACLITAXEL; PROTEIN CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP; TAXOIDS;

EID: 0034636084     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi992518p     Document Type: Article

References (39)

1. Schiff, P. B., Fant. J., and Horwitz, S. B. (1979) Nature (London) 277, 665-667.
2. Schiff, P. B., and Horwitz, S. B. (1981) Biochemistry 20, 3247-3252.
3. Hamel, E., Campo, A. A., Lowe, M. C., and Lin, C. M. (1981) J. Biol. Chem. 256(22), 11887-11894.
4. Kumar, N. (1981) J. Biol. Chem. 256(20), 10435-10441.
5. Schiff, P. B., and Horwitz, S. B. (1980) Proc. Natl. Acad. Sci. U.S.A. 77, 1561-1565.
6. Rowinsky, E. K., Donehower, R. C., Jones, R. J., and Tucker, R. W. (1988) Cancer Res. 48, 4093-4100.
7. Yvon, A. M., Wadsworth, P., and Jordan, M. A. (1999) Mol. Biol. Cell 10(4), 947-959.
8. Torres, K., and Horwitz, S. B. (1998) Cancer Res. 58, 3620-3626.
9. Parness, J., and Horwitz, S. B. (1981) J. Cell Biol. 91, 479-487.
10. Diaz, J. F., and Andreu, J. M. (1993) Biochemistry 32, 2747-2755.
11. Rao, S., Horwitz, S. B., and Ringel, I. (1992) J. Natl. Cancer Inst. 84, 785-788.
12. Rao, S., Krauss, N. E., Heerding, J. M., Swindell, C. S., Ringel, I., Orr, G. A., and Horwitz, S. B. (1994) J. Biol. Chem. 269(5), 3132-3134.
13. Rao, S., Orr, G. A., Chaudhary, A. G., Kingston, D. G. I., and Horwitz, S. B. (1995) J. Biol. Chem. 270(35), 20235-20238.
14. Rao, S., He, L., Chakravarty, S., Ojima, I., Orr, G. A., and Horwitz, S. B. (1999) J. Biol. Chem. 274(53), 37990-37994.
15. Parness, J., Kingston, D. G. I., Powell, R. C., Harracksingh, C., and Horwitz, S. B. (1982) Biochem. Biophys. Res. Commun. 105(3), 1082-1089.
16. Lataste, H., Senilh, V., Wright, M., Guenard, D., and Potier, P. (1984) Proc. Natl. Acad. Sci. U.S.A. 81, 4090-4094.
17. Georg, I. G., Chen, T. T., Ojima, I., and Vyas, D. M. (1994) Taxane Anticancer Agents, Basic Science and Current Status. ACS Symposium Series 583.
18. Chaudhary, A. G., Gharpure, M. M., Rimoldi, J. M., Chordia, M. D., Gunatilaka, A. A. L., Kingston, D. G. I., Grover, S., Lin, C. M., and Hamel, E. (1994) J. Am. Chem. Soc. 116, 4097-4098.
19. Grover, S., Rimoldi, J. M., Molinero, A. A., Chaudhary, A. G., Kingston, D. G. I., and Hamel, E. (1995) Biochemistry 34, 3927-3934.
20. Chen, S., Farina, V., Wei, J., Long, B., Fairchild, C., Mamber, S. W., Kadow, J. F., Vyas, D., and Doyle, T. W. (1994) Bioorg. Med. Chem. Lett. 4, 479-482.
21. Kingston, D. G. I., Chaudhary, A. G., Chordia, M. D., Gharpure, M. M., Gunatilaka, A. A. L., Higgs, P. I., Rimoldi, J. M., Samala, L., Jagtap, P. G., Giannakakou, P., Jiang, Y. Q., Lin, C. M., Hamel, E., Long, B. H., Fairchild, C. A., and Johnston, K. A. (1998) J. Med. Chem. 41, 3715-3726.
22. Weisenberg, R. C. (1972) Science 177, 1104-1105.
23. Shelanski, M. L., Gaskin, F., and Cantor, C. R. (1973) Proc. Natl. Acad. Sci. U.S.A. 70, 765-768.
24. Kavallaris, M., Kuo, D. Y., Burkhart, C. A., Regl, D. L., Norris, M. D., Haber, M., and Horwitz, S. B. (1997) J. Clin. Invest. 100(5), 1282-1293.
25. Bollag, D. M., McQueney, P. A., Zhu, J.. Hensens, O., Koupal, L., Liesch, J., Goetz, M., Lazarides, E., and Woods, C. M. (1995) Cancer Res. 55, 2325-2333.
26. Nogales, E., Wolf, S. G., and Downing, K. H. (1998) Nature 391, 199-202.
27. Nogales, E., Whittaker, M., Milligan, R. A., and Downing, K. H. (1999) Cell 96, 79-88.
28. Amos, L. A., and Löwe, J. (1999) Chem. Biol. 6, R65-R69.
29. Kowalski, R. J., Giannakakou, P., and Hamel, E. (1997) J. Biol. Chem. 274(4), 2534-2541.
30. Haar, E., Kowalski, R. J., Lin, C. M., Longley, R. E., Gunasekera, S. P., Rosenkranz, H. S., and Day, B. W. (1996) Biochemistry 35, 243-250.
31. Hung, D. T., Chen, J., and Schreiber, S. L. (1996) Chem. Biol. 3(4), 287-293.
32. Lindel, T., Jensen, P. R., Fenical, W., Long, B. H., Casazza, A. M., Carboni, J. M., and Fairchild, C. R. (1997) J. Am. Chem. Soc. 119, 8744-8745.
33. Long, B. H., Carboni, J. M., Wasserman, A. J., Cornell, L. A., Casazza, A. M., Jensen, P. R., Lindel, T., Fenical, W., and Fairchild, C. R. (1998) Cancer Res. 58, 1111-1115.
34. Winkler, J. D., and Axelsen, P. H. (1996) Bioorg. Med. Chem. Lett. 6(24), 2963-2966.
35. Ojima, I., Chakravarty, S., Inoue, T., Lin, S. N., He, L., Horwitz, S. B., Kuduk, S. D., and Danishefsky, S. J. (1999) Proc. Natl. Acad. Sci. U.S.A. 96, 4256-4261.
36. Su, D. S., Balog, A., Meng, D., Bertinato, P., Danishefsky, S. J., Zheng, Y. H., Chou, T. C., He, L., and Horwitz, S. B. (1997) Angew. Chem., Int. Ed. Engl. 36(19), 2093-2096.
37. Nicolaou, K. C., Vourloumis, D., Li, T., Pastor, J., Winssinger, N., He, Y., Ninkovic, S., Sarabia, F., Vallberg, H., Roschangar, F., King, N. P., Finlay, R. V., Giannakakou, P., Verdier-Pinard, P., and Hamel, E. (1997) Angew. Chem., Int. Ed. Engl. 36(19), 2097-2103.
38. McDaid, H. M., Bhattacharya, S. K., Chen, X. T., He, L., Shen, H. J., Gutteridge, C. E., Horwitz, S. B., and Danishefsky, S. J. (1999) Cancer Chemother. Pharmacol. 44, 131-137.
39. Gueritte-Voegelein, F., Mangatal, L., Guenard, D., Potier, P., Guilhem, J., Cesario, M., and Pascard, C. (1990) Acta Crystallogr. C46, 781-784.