The coral-derived natural products eleutherobin and sarcodictyins A and B: Effects on the assembly of purified tubulin with and without microtubule- associated proteins and binding at the polymer taxoid site

Biochemistry

Volumn 38, Issue 17, 1999, Pages 5490-5498

  Hamel, Ernest ^a,d   Sackett, Dan L ^a   Vourloumis, Dionisios ^b,c   Nicolaou, K C ^b,c  

^a NATIONAL CANCER INSTITUTE   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DOCETAXEL; ELEUTHEROBIN; EPOTHILONE A; EPOTHILONE B; PACLITAXEL; SARCODICTYIN A; SARCODICTYIN B; TUBULIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER; CORAL; DRUG PROTEIN BINDING; HUMAN; HUMAN CELL; MICROTUBULE ASSEMBLY; POINT MUTATION; PRIORITY JOURNAL;

ALKALOIDS; ANIMALS; ANTINEOPLASTIC AGENTS; BINDING, COMPETITIVE; CNIDARIA; DITERPENES; EPOTHILONES; EPOXY COMPOUNDS; GROWTH INHIBITORS; GUANOSINE TRIPHOSPHATE; HUMANS; MICROTUBULE-ASSOCIATED PROTEINS; PACLITAXEL; POLYMERS; PROTEIN BINDING; PROTEIN PROCESSING, POST-TRANSLATIONAL; TAXOIDS; THIAZOLES; TUBULIN; TUMOR CELLS, CULTURED;

ANTHOZOA;

EID: 0033609037     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi983023n     Document Type: Article

References (39)

1. Hamel, E. (1996) Med. Res. Rev. 16, 207-231.
2. Gunasekera, S. P., Gunasekera, M., Longley, R. E., and Schulte, G. K. (1990) J. Org. Chem. 55, 4912-4915; with erratum (1991) 56, 1346.
3. Gunasekera, S. P., Gunasekera, M., Longley, R. E., and Schulte, G. K. (1990) J. Org. Chem. 55, 4912-4915; with erratum (1991) 56, 1346.
4. Ter Haar, E., Kowalski, R. J., Hamel, E., Lin, C. M., Longley, R. E., Gunasekera, S. P., Rosenkranz, H. S., and Day, B. W. (1996) Biochemistry 35, 243-250.
5. Mooberry, S. L., Tien, G., Hernandez, A. H., Plubrukarn, A., and Davidson, B. S. (1999) Cancer Res. 59, 653-660.
6. D'Ambrosio, M., Guerriero, A., and Pietra, F. (1987) Helv. Chim. Acta 70, 2019-2027.
7. D'Ambrosio, M., Guerriero, A., and Pietra, F. (1988) Helv. Chim. Acta 71, 964-976.
8. Ketzinel, S., Rudi, A., Schleyer, M., Benayahu, Y., and Kashman, Y. (1996) J. Nat. Prod 59, 873-875.
9. Fenical, W. H., Hensen, P. R., and Lindel, T. (1995) United States patent 5473057.
10. Lindel, T., Jensen, P. R., Fenical, W., Long, B. H., Casazza, A. M., Carboni, J., and Fairchild, C. R. (1997) J. Am. Chem. Soc. 119, 8744-8745.
11. 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.
12. Rowinsky, E. K., and Donehower, R. C. (1995) N. Engl. J. Med. 332, 1004-1014.
13. Cortes, J. E., and Pazdur, R. (1995) J. Clin. Oncol. 13, 2643-2655.
14. Nicolaou, K. C., Xu, J.-Y., Kim, S., Ohshima, T., Hosokawa, S., and Pfefferkorn, J. (1997) J. Am. Chem. Soc. 119, 11353-11354.
15. Nicolaou, K. C., van Delft, F., Ohshima, T., Vourloumis, D., Xu, J., Hosokawa, S., Pfefferkorn, J., Kim, S., and Lee, T. (1997) Angew. Chem., Int. Ed. Engl. 36, 2520-2524.
16. Chen, X.-T., Zhou, B., Bhattacharya, S. K., Gutteridge, C. E., Pettus, T. R. R., and Danishefsky, S. J. (1998) Angew. Chem., Int. Ed. 37, 789-792.
17. Nicolaou, K. C., Kim, S., Pfefferkorn, J., Xu, J., Ohshima, T., Hosokawa, S., Vourloumis, D., and Li, T. (1998) Angew. Chem., Int. Ed. 37, 1418-1421.
18. Nicolaou, K. C., Xu, J. Y., Kim, S., Pfefferkorn, J., Oshima, T., Vourloumis, D., and Hosokawa, S. (1998) J. Am. Chem. Soc. 720, 8661-8673.
19. Nicolaou, K. C., Oshima, T., Hosokawa, S., Van Delft, F. L., Vourloumis, D., Xu, J. Y., Pferrerkorn, J., and Kim, S. (1998) J. Am. Chem. Soc. 120, 8674-8680.
20. Nicolaou, K. C., Winssinger, N., Vourloumis, D., Ohshima, T., Kim, S., Pfefferkorn, J., Xu, J.-Y., and Li, T. (1998) J. Am. Chem. Soc. 120, 10814-10826.
21. Ciomei, M., Albanese, C, Pastori, W., Grandi, M., Pietra, F., D'Ambrosio, M., Guerriero, A., and Battistini, C. (1997) Proc. Am. Assoc. Cancer Res. 38, 5.
22. 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.
23. 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, M. R. V., Giannakakou, P., Verdier-Pinard, P., and Hamel, E. (1997) Angew. Chem., Int. Ed. Engl. 36, 2097-2103.
24. Hamel, E., and Lin, C. M. (1984) Biochemistry 23, 4173-4184.
25. Grover, S., and Hamel, E. (1994) Eur. J. Biochem. 222, 163-172.
26. Lin, C. M., Jiang, Y, Q., Chaudhary, A. G., Rimoldi, J. M., Kingston, D. G. I., and Hamel, E. (1996) Cancer Chemother. Pharmacol. 38, 136-140.
27. Kowalski, R. J., Giannakakou, P., and Hamel, E. (1997) J. Biol. Chem. 272, 2534-2541.
28. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., and Boyd, M. R. (1990) J. Natl. Cancer Inst. 82, 1107-1112.
29. Giannakakou, P., Sackett, D. L., Kang, Y.-K., Zhan, Z., Buters, J. T. M., Fojo, T., and Poruchynsky, M. S. (1997) J. Biol. Chem. 272, 17118-17125.
30. Kingston, D. G. I., Chaudhary, A. G., Chordia, M. D., Gharpure, 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. R., and Johnston, K. A. (1998) J. Med. Chem. 41, 3715-3726.
31. Hamel, E., Lustbader, J., and Lin, C. M. (1984) Biochemistry 23, 5314-5325.
32. Dixon, M., Webb, E. C., Thorne, C. J. R., and Tipton, K. F. (1979) Enzymes, 3rd ed., Academic Press, New York.
33. Pettit, G. R., Srirangam, J. K., Barkoczy, J., Williams, M. D., Boyd, M. R., Hamel, E., Pettit, R. K., Hogan, F., Bai, R., Chapuis, J.-C., McAllister, S. C., and Schmidt, J. M. (1998) Anti-Cancer Drug Des. 13, 243-277.
34. Mellado, W., Magri, N. F., Kingston, D. G. I., Garcia-Arenas, R., Orr, G. A., and Horwitz, S. B. (1984) Biochem. Biophys. Res. Commun. 124, 329-336.
35. Georg, G., Ali, S. M., Stella, V. J., Waugh, W. N., and Himes, R. H. (1998) Bioorg. Med. Chem. Lett. 8, 1959-1962.
36. Kowalski, R. J., Giannakakou, P., Gunasekera, S. P., Longley, R. E., Day, B. W., and Hamel, E. (1997) Mol. Pharmacol. 52, 613-622.
37. Nogales, E., Wolf, S. G., and Downing, K. H. (1998) Nature (London) 391, 199-203.
38. Derry, W. B., Wilson, L., and Jordan, M. A. (1995) Biochemistry 34, 2203-2211.
39. Höfle, G., Bedorf, N., Steinmetz, H., Schomburg, D., Gerth, K., and Reichenbach, H. (1996) Angew. Chem., Int. Ed. Engl. 35, 1567-1569.