Synthetic microtubule inhibitors

Drugs of the Future

Volumn 21, Issue 1, 1996, Pages 65-70

  Raynaud, Florence I ^a   Judson, Ian R ^a  

^a INSTITUTE OF CANCER RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIHYDROPYRIDO[3,4 B]PYRAZINE DERIVATIVE; 1069C85; ANTINEOPLASTIC AGENT; CEMADOTIN; CHALCONE DERIVATIVE; COLCHICINE; COLCHICINE DERIVATIVE; DOLASTATIN; ESTRAMUSTINE; MICROTUBULE ASSOCIATED PROTEIN; MIVOBULIN ISETHIONATE; NOCODAZOLE; THIOCOLCHICINE; UNCLASSIFIED DRUG; VINBLASTINE;

ANTINEOPLASTIC ACTIVITY; BONE MARROW SUPPRESSION; DRUG BLOOD LEVEL; DRUG INTERACTION; DRUG PROTEIN BINDING; HUMAN; MICROTUBULE ASSEMBLY; NEUROTOXICITY; NONHUMAN; REVIEW;

EID: 0029927522     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.1996.021.01.340133     Document Type: Review

References (63)

1. Feit, H., Neudeck, U., Bassin, F. Comparison of the isoelectric and molecular and properties of tubulin subunits. J Neurochem 1977, 28: 697-702.
2. Dustin, P. (Ed.). Microtubules, 2nd Edition. Springer Verlag: New York 1984.
3. Sage, C.R., Dougherty, C.A., Davis, A.S., Burns, R.G., Wilson, L , Farell, R.G. Site directed mutagenesis of putative GTP binding sites of yeast B-tubulin. Evidence that α-tubulins, β-tubulins and γ-tubulins are atypical GTPases. Biochemistry 1995, 34: 7409-19.
4. Kirschner, M.W., Mitchison, T. Beyond self assembly: From microtubule to morphogenesis. Cell 1986, 45: 329-42.
5. Kirschner, M.W., Mitchison, T. Scientific correspondence: Microtubule dynamics. Nature 1986, 324: 621-2.
6. Avila, J. Microtubule dynamics. FASEB J 1990, 4: 3284-90.
7. Olmsted, J.B., Asnes, C.F., Parysek, L.M., Lyon, H.D., Kidder, G.M. Distribution of MAP in cells and in adult and developing mice tissues. Ann NY Acad Sci 1986, 466: 292-305.
8. Taylor, E.W. The mechanism of colchicine inhibition of mitosis. J Cell Biol 1965, 25, 145-60.
9. Olmstead, J.B., Borisy, G.G. Characterization of microtubule assembly in porcine brain extracts by viscosimetry. Biochemistry 1973, 12: 4282-9.
10. Battachara, B., Wolff, J. Promotion of fluorescence upon binding of colchicine to tubutin. Proc Natl Acad Sci USA 1974, 71: 2627-32.
11. Andreu, J.M., Timasheff, S.N. Tubulin bound to colchicine form polymers different from microtubule. Biochemistry 1982, 21: 6465-76.
12. Medrano, F.J., Andreu, J.M., Gorbunoff, M.J., Timasheff, S.N. Roles of colchicine rings B and C in the binding process to tubulin. Biochemistry 1989, 28: 5598-9.
13. Garland, D. L. Kinetics and mechanism of colchicine binding to tubulin: Evidence for ligand-induced conformational changes. Biochemistry 1978, 17: 4266-72.
14. Lambeir, A., Engelborghs, Y. A fluorescence stopped flow study of colchicine binding to tubulin. J Biol Chem 1981, 256: 3279-82.
15. Banerjee, A., Ludena, R.F. Kinetics of association and dissociation of colchicine complexes from brain and renal tubulin with different affinities to colchicine. FEBS Lett 1987, 219: 103-7.
16. Timasheff, S N., Andreu, J.M , Na, G.C. Physical and spectroscopic methods for the evaluation of the interaction of antimitotic agents with tubulin. Pharmacol Ther 1991, 52: 191-210.
17. Kang, G.J., Getahung, Z., Muzzafar, A., Brossi, A., Hamel, H. N-Acetyl colchinol O-methyl ether and thiocolchicine, potent analogues of colchicine modified in the C ring. J Biol Chem 1990, 265: 10355-9.
18. Edwards, M.L., Stemerick, D.M., Sunkara, PS Chalcones: A novel class of antimitotic agents. J Med Chem 1990, 33: 1948-60.
19. Peyrot, V., Briand, C. Silence, K., AD'Hoore, A.D., Englborghs, Y. Mechanism of binding of the new antimitotic drug MDL27048 to the colchicine binding site of tubulin: Equilibrium studies. Biochemistry 1992, 31. 11125-31.
20. Silence, K , AD'Hoore, A.D., Englborghs, Y., Peyrot, V., Briand, C. Fluorescence stopped flow studies of the interaction of tubulin with the antitmitotic drug MDL27048. Biochemistry 1992, 31: 11133-7.
21. Weis, A.L., Dexter, D L , Taylor, B. et al Synthesis and biological evaluation of a new series of tubulin active molecules. Proc Amer Assoc Cancer Res 1994, 35 Abst 2409.
22. Temple, C., Wheeler, G.P., Elliot, R.D. et al. New anticancer agents: Synthesis of 1,2-dihydropyrido[3,4-b]pyrazines (1-deaza7,8-dihydropteridines). J Med Chem 1982, 25: 1045-50.
23. Wheeler, G.P., Bowdon, B.J., Temple, C., Adamson, D.J., Webster, J. Biological effects and structure-activity relationships of 1,2-dihydropyrido[3,4-b] pyrazines. Cancer Res 1983, 43: 3567-75.
24. Temple, C., Wheeler, G.P., Elliot, R.D., Rose, J.D., Comber, R.N., Montgomery, J.A. 1,2-Dihydropyrido[3,4-b]pyrazines: Structure activity relationships. J Med Chem 1983, 26: 91-5.
25. Bowdon, B.J., Waud, W.R., Wheeler, G.P., Hain, R., Dansby, L., Temple, C. Comparison of 1,2-dihydropyrido[3,4-b]pyrazines (1-deaza-7,8-dihydropteridines) with several other inhibitors of mitosis. Cancer Res 1987, 47: 1621-6.
26. Temple, C., Rener, G.A. New anticancer agents: Chiral isomers of ethyl-5 amino-1,2-dihydro-2-methyl-3-phenylpyrido[3,4-b] pyrazine-7-carbamate. J Med Chem 1989, 32: 2089-92.
27. De Ines, C., Leynadier, D., Barasoin, I. et al. Inhibition of microtubule and cell cycle arrest by a new 1-deaza-7,8-dihydropteridine antitumour drug CI-980 and by its chiral isomer NSC613863. Cancer Res 1994, 54: 75-84.
28. McDonald, J.R., Peggs, D.G. Extravasation injury potential of CI-980 a novel synthetic mitotic inhibitor. Cancer Chemother Pharmacol 1993, 32: 365-7.
29. Sklarin, N.T., Benson, J., Roca, J. et al. Phase I study of CI-980: 24-hr infusion schedule. Proc Amer Assoc Clin Oncol 1995, 14: Abst 1559.
30. Rowinski, E.K., Noe, D.A., Grochow, M.K. et al. Phase I and pharmacological study of CI-980, a synthetic and structurally unique antimicrotubule agent, on a 72-hour continuous infusion schedule in adults with solid tumors. Proc Amer Assoc Clin Oncol 1995, 14: Abst 1477.
31. Pazdur, R., Diaz-Canton, E., Meyers, C. et al. Phase II trial of CI-980 in metastatic colorectal carcinoma patients. Proc Amer Assoc Clin Oncol 1995, 14: Abst 511.
32. Verschraegen, C.F., Kudelka, A.P., Edwards, C.L. et al. Phase II trial of CI-980 in advanced epithelial ovarian carcinoma. Proc Amer Assoc Clin Oncol 1995, 14: Abst 754.
33. De Brabander, I.J., Van de Veire, R.M.L., Aerts, F.E.M., Borgers, M., Janssen, P A.J. The effect of methyl [5-(2-thienylcarbonyl)-H-benzimidazo-2-yl] carbamate (R 17394, NSC 238159) a new synthetic antitumor drug interfering with microtubules on mammalian cells cultured in vitro Cancer Res 1976 36: 905-16.
34. Arai, T. Inhibition of microtubule assembly in vitro by TN-16 a synthetic antitumor drug. FEBS Lett 1983, 155. 273-6.
35. Gupta, R.S. Cross resistance of nocodazole-resistant mutants of CHO cells towards other microtubule inhibitors: Similar mode of action of benzimidazole carbamate derivatives and NSC 181928 and TN-16. Mol Pharmacol 1986, 15: 201-5.
36. Hodgson, S.T., Jenkins, D.C., Knick, V., Rapson, E., Watts, S.D.M. Synthesis and biological properties of 1069C85: A new synthetic antitumor agent with very low cross resistance potential. Bioorg Med Chem Lett 1992, 10: 1257-62.
37. Hodgson, S.T. Discovery of 1069C - A novel synthetic antitumor agent with low cross resistance potential. In: Medicinal Chemistry: Principles and Practice. King, F.D. (Ed.). Royal Society of Chemistry: Cambridge 1994, 241-51.
38. Raynaud, F.I., Lelland, L.R., Walton, M.I., Judson I.R. Preclinical pharmacology of 1069C85 a novel tubulin binder. Cancer Chemother Pharmacol 1994, 35: 169-74.
39. Raynaud, F.I., Walton, M., Judson, I.R. High performance liquid chromatographic assay for the measurement of the novel microtubule inhibitor 1069C85 in biological tissues and fluids. J Chromatogr Biomed Appl 1993, 622: 243-8.
40. Judson, I., Berry, C., Hanwell, J. et al. Phase I trial and pharmacokinetics of the orally administered tubulin binder 1069C. Proc Amer Assoc Clin Oncol 1995, 14: Abst 1524.
41. Fujiwara, K., Tilney, L.G. Substructure analysis of the microtubule and its polymorphic forms. Ann NY Acad Sci 1975, 253: 27-50.
42. Owellen, R.J., Owens, A.H., Donigan, D.W. The binding of vincristine, vinblastine and colchicine to tubulin. Biochem Biophys Res Commun 1972, 23: 685-91.
43. Conrad, R.A., Cullinan, G.J., Gerzon, K., Poore, G.A. Structure activity relationships of dimeric Ctharantus alkaloids. Experimental antitumor activity of n-substituted deacetyl vinblastine amide (vindsine sulfates). J Med Chem 1979: 22, 391-8.
44. a) Bhattacharyya, B., Wolff, J. Tubulin aggregation and disaggregation: Mediation by two distinct vinblastine-binding sites. Proc Natl Acad Sci 1976, 73: 2375-81.
45. b) Pettit, G.R., Kamano, Y., Herald, C L. et al. The isolation and structure of a remarkable marine animal antineoplastic constituent: Dolastatin 10. J Amer Chem Soc 1987, 109: 6883-7.
46. Pettit, G.R., Kamano, Y., Kizu, H. et al. Isolation and structure of the cytostatic linear depsipeptide dolastatin 15. J Org Chem 1989, 54: 6005.
47. Pettit, G.R., Herald, D.L., Singh, S.B., Thornton T.J., Mullany, T.J. Antineoplastic agents. Synthesis of natural dolastatin 15. J Amer Chem Soc 1991, 113: 6692-5.
48. Roux, F., Maugras, I., Poncet, J., Niel, G., Jouin, P. Synthesis of dolastatin 10 and R-Doe-dolastatin 10. Tetrahedron 1994, 50: 5345.
49. Patino, N., Frerot, E., Galeotti, N. et al. Total synthesis of the proposed structure of dolastatin 15. Tetrahedron 1992, 48: 4115-8.
50. Bai, R., Friedrnan, S.J., Pettit, G.R., Hamel, E. Dolastatin 15, a potent antimitotic depsipeptide derived from Dolabella auricularia. Biochem Pharmacol 1992, 43: 2637.
51. Smith, P., Nelson, C., Janssen, B., Haupt, A., Bartozzan, T. Preclinical antitumor activity of a novel water-soluble dolastatin 15 analog (LU103793). Proc Amer Assoc Cancer Res 1995, 36; Abst 2345.
52. Villalona-Calero, M., Degen, D., Barlozzari, T., Von Hoff, D. LU 103793 evaluation by human tumor clonogenic assay of a novel dolastatin. Proc Amer Assoc Cancer Res 1995, 36: Abst 2349.
53. Smith, P., Nelson, C., Spigelman, M., Robinson, S., Barlozzan, T. In vivo antitumor activity of LU103793: Evidence for schedule dependency in MX-1, KB3-1, and P388 tumor models. Proc Amer Assoc Cancer Res 1995, 36: Abst 2348.
54. Fex, H.J., Hogberg, K.B., Konyves, I., Kneip, P.O.J. Certain steroids N-bis thaloethyl carbamates. US 3229104.
55. Tew, K.D. The mechanism of action of estramustine. Semin Oncol 1983, 10: 21-6.
56. Hartley-Asp, B. Estramustine-induced mitotic arrest in two human prostatic carcinoma cell lines, DU145 and PC-3. Prostate 1982, 5: 93-100.
57. Stearn, M.E., Tew, K.D. Antimicrotubule effect of estramustine an antiprostatic tumor drug. Cancer Res 1985, 45: 3891-7.
58. Moraga, D.M., Nuñez, P., Garrido, J., Maccioni, R.B. A tau fragment containing a repetitive sequence induces bundling of actin filaments. J Neurochem 1993, 61: 979-86.
59. Seidman, A., Scher, H., Petrylak, D. et al. Estramustine and vinblastine: Effects on prostate specific antigen in hormone-refractory prostate cancer. Proc Amer Assoc Cancer Res 1991, 32: A1113.
60. Cabral, F., Sobel, M., Gottesman, M. CHO mutants resistant to colchicine, colcemide or griseofulvin have an altered β-tubulin. Cell 1980, 20: 29-36.
61. Houghton, J.A., Houghton, P.J., Hazelton, B.J., Douglas, E.C. In situ selection of a human rhabdomyosarcoma resistant to vincristine with altered β-tubulin. Cancer Res 1985, 45: 2706-13.
62. Toppmyer, D.L., Slapak, C.A., Croop, J., Kufe, D.W. Interaction of dolastatin 10 with tubulin induction of aggregation and binding and dissociation reactions. Biochem Pharmacol 1994, 48: 609-12.
63. Tangwai, D.F., Brossi, A., Arnold, L.D., Gros, P. The nitrogen of the acetamido group of colchicine modulates P-glycoprotein-mediated multidrug resistance. Biochemistry 1993, 32: 6470-6.