Eleutherobin, a novel cytotoxic agent that induces tubulin polymerization, is similar to paclitaxel (taxolρ)

Cancer Research

Volumn 58, Issue 6, 1998, Pages 1111-1115

  Long, Byron H ^b   Carboni, Joan M ^b   Wasserman, Arthur J ^b   Cornell, Laurie A ^b   Casazza, Anna Maria ^a,b   Jensen, Paul R ^c   Lindel, Thomas ^c   Fenical, William ^c   Fairchild, Craig R ^b  

^a BAYER CORPORATION   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CYTOTOXIC AGENT; ELEUTHEROBIN; GLYCOPROTEIN P; PACLITAXEL; TUBULIN; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; COLON CARCINOMA; CROSS RESISTANCE; CYTOTOXICITY; DRUG ISOLATION; DRUG MECHANISM; HUMAN; HUMAN CELL; MICROTUBULE ASSEMBLY; PRIORITY JOURNAL;

ALKALOIDS; ANIMALS; ANTINEOPLASTIC AGENTS; BINDING SITES; BINDING, COMPETITIVE; CATTLE; COLONIC NEOPLASMS; DITERPENES; FEMALE; GROWTH INHIBITORS; HUMANS; MICROTUBULES; OVARIAN NEOPLASMS; PACLITAXEL; POLYMERS; TUBULIN; TUMOR CELLS, CULTURED;

EID: 0032520890     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (25)

1. Slichenmyer, W. J., and Von Hoff, D. D. Taxol: a new and effective anti-cancer drug. Anti-Cancer Drugs, 2: 519-530, 1991.
2. Chaudhry, V., Rowinsky, E. K., Sartorius, S. E., Donehower, R. C., and Cornblath, D. R. Peripheral neuropathy from Taxol and cisplatin combination chemotherapy: clinical and electrophysiological studies. Ann. Neurol., 35: 304-311, 1994.
3. ™). Ann. Oncol., 4: 610-611, 1993.
4. Schiff, P. B., and Horwitz, S. B. Taxol stabilizes microtubules in mouse fibroblast cells. Proc. Natl. Acad. Sci. USA, 77: 1561-1565, 1980.
5. Schiff, P. B., Fant, J., and Horwitz, S. B. Promotion of microtubule assembly in vitro by Taxol. Nature (Lond.), 277: 665-667, 1979.
6. 1 phase by interference with spindle formation during metaphase without affecting other microtubule functions during anaphase and telophase. Cancer Res., 54: 4355-4361, 1994.
7. Bruno, D., Sévenet, T., Morgat, M., Guénard, D., Moisand, A., Tollon, Y., Thoison, O., and Wright, M. Rhazinilam mimics the cellular effects of Taxol by different mechanisms of action. Cell Motil. Cytoskeleton, 28: 317-326, 1994.
8. ter Haar, E., Kowalski, R. J., Lin, C. M., Longley, R. E., Gunasekera, S. P., Rosenkranz, H. S., and Day, B. W. Discodermolide, a cytotoxic marine agent that stabilizes microtubules more potently than taxol. Biochemistry, 35: 243-250, 1996.
9. Bollag, D. M., McQueney, P. A., Zhu, J., Hensens, O., Koupal, L., Liesch, J., Goetz, M., Lazarides, E., and Woods, C. M. Epothilones, a new class of microtubule-stabilizing agents with a Taxol-like mechanism of action. Cancer Res., 55: 2325-2333, 1996.
10. Flam, F. Chemical prospectors scour the seas for promising drugs. Science (Washington DC), 266: 1324-1325, 1994.
11. Carté, B. K. Biomedical potential of marine natural products. Bioscience, 46: 271-286, 1996.
12. U. S. Letters Patent No. 5,473,057, issued December 5, 1995.
13. Lindel, T., Jensen, P. R., Fenical, W., Long, B. H., Casazza, A. M., Carboni, J., and Fairchild, C. R. Eleutherobin, a new cytotoxin class that mimics paclitaxel (Taxol) by stabilizing microtubules. J. Am. Chem. Soc., 119: 8744-8745, 1997.
14. Ciomei, M., Albanese, C., Pastori, W., Grandi, M., Pietra, F., D'Ambrosio, M., Guerriero, A., and Basttistini, C. Sarcodictyins: a new class of marine derivatives with mode of action similar to Taxol. Proc. Am. Assoc. Cancer Res., 38: 30, 1997.
15. Williams, R. C., Jr., and Lee, J. C. Preparation of tubulin from brain. Methods Enzymol., 85(D): 376-385, 1982.
16. Long, B. H., Wang, L., Lorico, A., Wang, R. R. C., Brattain, M. G., and Casazza, A. M. Mechanisms of resistance to etoposide and teniposide in acquired resistant human colon and lung carcinoma cell lines. Cancer Res., 51: 5275-5284, 1991.
17. Giannakakou, P., Sacket, D. L., Kang, Y-K., Zhan, Z., Buters, J. T. M., Fojo, T., and Poruchynsky, M. S. Paclitaxel-resistant human ovarian cancer cells have mutant β-tubulins that exhibit impaired paclitaxel-driven polymerization. J. Biol. Chem., 272: 17118-17125, 1997.
18. Scudiero. D. A., Shoemaker, R. H., Paull, K. D., Monks, A., Tierney, S., Nofziger, T. H., Currens, M. J., Seniff, D., and Boyd, M. R. Evaluation of a soluble tetrazolium/ formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Cancer Res., 48: 4827-4833, 1988.
19. Swindell, C. S., Krauss, N. E., Horwitz, S. B., and Ringel, I. Biologically active Taxol analogues with deleted A-ring side chain substituents and variable C-2′ configurations. J. Med. Chem., 34: 1176-1184, 1991.
20. Parness, J., and Horwitz, B. Taxol binds to polymerized tubulin in vitro. J. Cell Biol., 91: 479-487, 1981.
21. Bryan, J. A quantitative analysis of microtubule elongation. J. Cell Biol., 71: 749-767, 1976.
22. Long, B. H., Wasserman, A. J., Wei, J., Chen, S-H. and Kadow, J. F. Potent paclitaxel analogs that induce aberrant tubulin polymerization in vitro. Proc. Am. Assoc. Cancer Res., 37: 441, 1996.
23. Kennard, O., Watson, D. G., Riva di Sanseverino, L., Tursch, B., Bosmans, R., and Djerassi, C. Chemical studies of marine in vertebrates. IV. Terpenoids. LXII. Eunicellin, a diterpenoid of the Gorgonian Eunicella stricta: X-ray diffraction analysis of eunicellin dibromide. Tetrahedron Lett., 9: 2879-2884, 1968.
24. Bhalla, K., Ibrado, A. M., Tourkina, E., Tang, C., Mahoney, M. E., and Huang, Y. Taxol induces internucleosomal DNA fragmentation associated with programmed cell death in human myeloid leukemia cells. Leukemia (Baltimore), 7: 563-568, 1993.
25. Grover, S., Rimoldi, J. M., Molinero, A. A., Chaudhary, A. G., Kingston, D. G. I., and Hamel, E. Differential effects of paclitaxel (Taxol) analogs modified at positions C-2, C-7, and C-3′ on tubulin polymerization and polymer stabilization: identification of a hyperactive paclitaxel derivative. Biochemistry, 34: 3927-3934, 1996.