Natural, semisynthetic and synthetic microtubule inhibitors for cancer therapy

Drugs of the Future

Volumn 28, Issue 8, 2003, Pages 767-785

  Beckers, Thomas ^a   Mahboobi, Siavosh ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMITOTIC AGENT; ANTINEOPLASTIC AGENT; BETA TUBULIN; BMS 184476; BMS 188797; CISPLATIN; COLCHICINE; COLCHINOID DERIVATIVE; COMBRETASTATIN; CREMOPHOR; CRYPTOPHYCIN 52; CYCLOSPORIN; CYTOTOXIC AGENT; DOCETAXEL; DOLASTATIN; DOLASTATIN 10; DOLASTATIN 15; EPOTHILONE A; EPOTHILONE DERIVATIVE; ORTATAXEL; PACLITAXEL; PACLITAXEL DERIVATIVE; RPR 109881A; SP 1010C; TAXOEXTRA; TRASTUZUMAB; TXD 258; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINBLASTINE; VINCA ALKALOID; VINCRISTINE; XIOTAX;

CANCER CHEMOTHERAPY; CLINICAL TRIAL; CYTOTOXICITY; DRUG BINDING; DRUG BIOAVAILABILITY; DRUG CLEARANCE; DRUG EFFICACY; DRUG ISOLATION; DRUG RESISTANCE; DRUG TOLERABILITY; DRUG TOXICITY; HUMAN; MITOSIS SPINDLE; REVIEW;

EID: 0242386588     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.2003.028.08.744356     Document Type: Review

References (129)

1. Hanahan, D., Weinberg, R.A. The hallmarks of cancer. Cell 2000, 100: 57-70.
2. Nigg, E.A. Polo-like kinases: Positive regulators of cell divisions from start to finish. Curr Opin Cell Biol 1998, 10: 776-93.
3. Wittmann, T., Hyman, A., Desai, A. The spindle: A dynamic assembly of microtubules and motors. Nat Cell Biol 2001, 3: E28-34.
4. Nicklas, R.B. How cells get the right chromosomes. Science 1997, 275: 632-7.
5. Amos, L.A. Focusing-in on microtubules. Curr Opin Struct Biol 2000, 10: 236-41.
6. Nogales, E., Wolf, S.G., Downing, K.H. Structure of the alpha beta tubulin dimer by electron crystallography. Nature 1998, 391: 199-203.
7. Downing, K.H., Nogales, E. Tubulin structure: Insights into microtubule properties and functions. Curr Opin Struct Biol 1998, 8: 785-91.
8. Ludena, R.F. Multiple forms of tubulin: Different gene products and covalent modifications. Int Rev Cytology 1998, 187: 207-75.
9. Hubbert, C., Guardiola, A., Shao, R. et al. HDAC6 is a microtubule-associated deacetylase. Nature 2002, 417: 455-8.
10. Mitchison, T., Kirschner, M. Dynamic instability of microtubule growth. Nature 1984, 312: 237-42.
11. Andersen, S.S. Spindle assembly and the art of regulating microtubule dynamics by MAPs and Stathmin/Op18. Trends Cell Biol 2000, 10: 261-7.
12. Drewes, G., Ebneth, A., Mandelkow, E.M. MAPs, MARKs and microtubule dynamics. Trends Biochem Sci 1998, 23: 307-11.
13. Pohle, K., Matthies, E., Peters, J.E. On the tumor growth-inhibiting action of colchicine. Arch Geschwulstforsch 1965, 25: 17-20.
14. Owellen, R.J., Owens, A.H. Jr., Donigian, D.W. The binding of vincristine, vinblastine and colchicine to tubulin. Biochem Biophys Res Commun 1972, 47: 685-91.
15. Wani, M.C., Taylor, H.L., Wall, M.E., Coggon, P., McPhail, A.T. Plant antitumor agents. VI. The isolation and structure of Taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 1971, 93: 2325-7.
16. Snyder, J.P., Nettles, J.H., Cornett, B., Downing, K.H., Nogales, E. The binding conformation of Taxol in β-tubulin: A model based on electron crystallographic density. Proc Natl Acad Sci USA 2001, 98: 5312-6.
17. Schiff, P.B., Fant, J., Horwitz, S.B. Promotion of microtubule assembly in vitro by Taxol. Nature 1979, 277: 665-7.
18. Crown, J., O'Leary, M. The taxanes: An update. Lancet 2000, 355: 1176-8.
19. Jordan, A., Hadfield, J.A., Lawrence, N.J., McGown, A.T. Tubulin as a target for anticancer drugs: Agents which interact with the mitotic spindle. Med Res Rev 1998, 18: 259-796.
20. Li, Q., Sham, H.L., Rosenberg, S.H. Antimitotic agents. Ann Rep Med Chem 1999, 34: 139-48.
21. Wood, K.W., Cornwell, W.D., Jackson, J.R. Past and future of the mitotic spindle as an oncology target. Curr Opin Pharmacol 2001, 1: 370-7.
22. Malingre, M.M., Richel, D.J., Beijnen, J.H. et al. Coadministration of cyclosporine strongly enhances the oral bioavailability of docetaxel. J Clin Oncol 2001, 19: 1160-6.
23. Dumontet, C., Sikic, B. I. Mechanisms of action of and resistance to antitubulin agents: Microtubule dynamics, drug transport, and cell death. J Clin Oncol 1999, 17: 1061-70.
24. Monzo, M., Rosell, R., Sanchez, J.J. Paclitaxel resistance in non-small-cell lung cancer associated with β-tubulin gene mutations. J Clin Oncol 1999, 17: 1786-93.
25. Giannakakou, P., Sackett, D.L., Kang, Y.K. et al. Paclitaxel-resistant human ovarian cancer cells have mutant β-tubulins that exhibit impaired paclitaxel-driven polymerization. J Biol Chem 1997, 272: 17118-25.
26. Kavallaris, M., Kuo, D.Y., Burkhart, C.A. et al. Taxol-resistant epithelial ovarian tumors are associated with altered expression of specific beta-tubulin isotypes. J Clin Invest 1997, 100: 1282-93.
27. Bissery, M.C. Preclinical evaluation of new taxoids. Curr Pharm Des 2001, 7: 1251-7.
28. Distefano, M., Scambia, G., Ferlini, C. et al. Anti-proliferative activity of a new class of taxanes (14β-hyydroxy-10-deacetylbaccatin III derivatives) on multidrug-resistance-positive human cancer cells. Int J Cancer 1997, 72: 844-50.
29. Nicoletti, M.I., Colombo, T., Rossi, C. et al. IDN5109, a taxane with oral bioavailability and potent antitumor activity. Cancer Res 2000, 60: 842-6.
30. Polizzi, D., Pratesi, G., Monestiroli, S. et al. Oral efficacy and bioavailability of a novel taxane. Clin Cancer Res 2000, 6: 2070-4.
31. Altstadt, T.J., Fairchild, C.R., Golik, J. et al. Synthesis and antitumor activity of novel C-7 paclitaxel ethers: Discovery of BMS-184476. J Med Chem 2001, 44: 4577-83.
32. Rose, W.C., Fairchild, C., Lee, F.Y. Preclinical antitumor activity of two novel taxanes. Cancer Chemother Pharmacol 2001, 47: 97-105.
33. Hidalgo, M., Aylesworth, C., Hammond, L.A. et al. Phase I and pharmacokinetic study of BMS-184476, a taxane with greater potency and solubility than paclitaxel. J Clin Oncol 2001, 19: 2493-503.
34. Vrignaud, P., Lejeune, P., Bissery, M.C. TXD258, a new taxoid, with oral activity. Proc Am Assoc Cancer Res 2001, 42: Abst 1975.
35. Dykes, D.J., Sarsat, J. P., Bissery, M.C. Efficacy evaluation of TXD258, a taxoid compound, against orthotopic and subcutaneous glioblastomas. Proc Am Assoc Cancer Res 2000, 41: 301.
36. Gelmon, K.A., Latreille, J., Tolcher, A. et al. Phase I dose-finding study of a new taxane, RPR 109881A, administered as a one-hour intravenous infusion days 1 and 8 to patients with advanced solid tumors. J Clin Oncol 2000, 18: 4098-108.
37. Groth, G. et al. Preliminary analysis of phase II data for LY-355703 results in trial suspension. Eur J Cancer 2001, 37 (Suppl. 6): Abst 167.
38. Vaishampayan, U., Glode, M., Du, W. et al. Phase II study of dolastatin-10 in patients with hormone-refractory metastatic prostate adenocarcinoma. Clin Cancer Res 2000, 6: 4205-8.
39. Saad, E.D., Kraut, E.H., Hoff, P.M. et al. Phase II study of dolastatin-10 as first-line treatment for advanced colorectal cancer. Am J Clin Oncol 2002, 25: 451-3.
40. Hoefle, G., Bedorf, N., Steinmetz, H., Schomburg, D., Gerth, K., Reichenbach, H. Epothilone A and B - novel 16-membered macrolides with cytotoxic activity: Isolation, crystal structure and conformation in solution. Angew Chem Int Ed Engl 1996, 35: 1567-9.
41. Kowalski, R.J., Giannakakou, P., Hamel, E. Activities of the mirotubule-stabilizing agents epothilones A and B with purified tubulin and in cells resistant to paclitaxel (Taxol®). J Biol Chem 1997, 272: 2534-41.
42. Bollag, D.M., McQueney, P.A., Zhu, J. et al. Epothilones, a new class of microtubule-stabilizing agents with a Taxol-like mechanism of action. Cancer Res 1995, 55: 2325-33.
43. Muhlradt, P.F., Sasse, F. Epothilone B stabilizes microtubuli of macrophages like Taxol without showing Taxol-like endotoxin activity. Cancer Res 1997, 57: 3344-6.
44. Rosen, L., Kabbinavar, F., Rosen, P. et al. Phase I dose-escalating trial of KOS-862 (epothilone D) in patients with advanced malignancies. Eur J Cancer 2002, 38(Suppl. 7): 41.
45. Calvert, P.M. et al. A phase I clinical trial and pharmacokinetic study of EP0906 (epothilone B) in patients with advanced solid tumors. EORTC Meeting Amsterdam 2002, Abst 575.
46. Lee, F.Y., Borzilleri, R., Fairchild, C.R. et al. BMS-247550: A novel epothilone analog with a mode of action similar to paclitaxel but possessing superior antitumor efficacy. Clin Cancer Res 2001, 7: 1429-37.
47. Fojo, A.T. et al. A phase I clinical trial of BMS-247550 (NSC 710428), an epothilone B analog, in patients with refractory carcinoma. AACR-NCI-EORTC Conference Miami 2001, Abst 774.
48. McDaid, H.M., Mani, S., Shen, H.J., Muggia, F., Sonnichsen, D., Horwitz, S.B. Validation of the pharmacodynamics of BMS-247550, an analogue of epothilone B, during a phase I clinical study. Clin Cancer Res 2002, 8: 2035-43.
49. Hamel, E., Sackett, D.L., Vourloumis, D., Nicolau, K.C. 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 1999, 38: 5490-8.
50. Nicolau, K.C., Pfefferkorn, J., Xu, J. et al. Total synthesis and chemical biology of the sarcodictyins. Chem Pharm Bull (Tokyo) 1999, 47: 199-213.
51. Long, B.H., Carboni, J.M., Wasserman, A.J. et al. Eleutherobin, a novel cytotoxic agent that induces tubulin polymerization, is similar to paclitaxel (Taxol). Cancer Res 1998, 58: 1111-5.
52. ter Haar, E., Kowalski, R.J., Hamel, E. et al. Discodermolide, a cytotoxic marine agent that stabilizes microtubules more potently than Taxol. Biochemistry 1996, 35: 243-50.
53. Paterson, I., Florence, G.J., Gerlach, K., Scott, J.P., Sereinig, N. A practical synthesis of (+)-discodermolide and analogues: Fragment union by complex aldol reactions. J Am Chem Soc 2001, 123: 9535-44.
54. Kowalski, R.J., Giannakakou, P., Gunasekera, S.P., Longley, R.E., Day, B.W., Hamel, E. The microtubule-stabilizing agent discodermolide competitively inhibits the binding of paclitaxel (Taxol) to tubulin polymers, enhances tubulin nucleation reactions more potently than paclitaxel, and inhibits the growth of paclitaxel-resistant cells. Mol Pharmacol 1997, 52: 613-22.
55. Martello, L.A., McDaid, H.M., Regl, D.L. et al. Taxol and discodermolide represent a synergistic drug combination in human carcinoma cell lines. Clin Cancer Res 2000, 6: 1978-87.
56. Giannakakou, P., Fojo, T. Discodermolide: Just another microtubule-stabilizing agent? No! A lesson in synergy. Clin Cancer Res 2000, 6: 1613-5.
57. Giannakakou, P., Gussio, R., Nogales, E. et al. A common pharmacophore for epothilone and taxanes: Molecular basis for drug resistance conferred by tubulin mutations in human cancer cells. Proc Natl Acad Sci USA 2000, 97: 2904-9.
58. Corley, D.G., Herb, R., Moore, R.E., Scheur, P.J., Paul, V.J. Laulimalide: New potent cytotoxic macrolides from a marine sponge and a nudibranch predator. J Org Chem 1988, 53: 3644-6.
59. Mooberry, S.L., Tien, G., Hernandez, A.H., Plubrukarn, A., Davidson, B.S. Laulimalide and isolaulimalide, new paclitaxel-like microtubule-stabilizing agents. Cancer Res 1999, 59: 653-60.
60. Paterson, I., De Savi, C., Tudge, M. Total synthesis of the microtubule-stabilizing agent (-)-laulimalide. Org Lett 2001, 3: 3149-52.
61. Eggen, M., Georg, G.I. The cryptophycins: Their synthesis and anticancer activity. Med Res Rev 2002, 2: 85-101.
62. Patel, V.F., Andis, S.L., Kennedy, J.H., Ray, J.E., Schultz, R.M. Novel cryptophycin antitumor agents: Synthesis and cytotoxicity of fragment "B" analogues. J Med Chem 1999, 42: 2588-603.
63. Liang, J., Moher, E.D., Moore, R.E., Hoard, D.W. Synthesis of cryptophycin 52 using the sharpless asymmetric dihydroxylation: Diol to epoxide transformation optimized for a base-sensitive substrate. J Org Chem 2000, 65: 3143-7.
64. Wagner, M.M., Paul, D.C., Shih, C., Jordan, M.A., Wilson, L., Williams, D.C. In vitro pharmacology of cryptophycin 52 (LY355703) in human tumor cell lines. Cancer Chem Pharmacol 1999, 43:115-25.
65. Panda, D., DeLuca, K., Williams, D., Jordan, M.A., Wilson, L. Antiproliferative mechanism of action of cryptophycin-52: Kinetic stabilization of microtubule dynamics by high-affinity binding to microtubule ends. Proc Natl Acad Sci USA 1998, 95: 9313-18.
66. Menon, K., Alvarez, E., Forler, P. et al. Antitumor activity of cryptophycins: Effects of infusion time and combination studies. Cancer Chemother Pharmacol 2000, 46: 142-9.
67. Pagani, O., Greim, G., Weigang, K. et al. Phase I clinical and pharmacodynamic study of the cryptophycin analog LY 355703 administered on an every 3 week schedule. Clin Cancer Res 1999, 5(Suppl.): Abst 8.
68. Takahashi, M., Iwasaki, S., Konayashi, H., Okuda, S., Murai, T., Sato, Y. Rhizoxin binding to tubulin at the maytansine-binding site. Biochim Biophys Acta 1987, 926: 215-23.
69. Garcia-Rocha, M., Garcia-Gravalos, M.D., Avila, J. Characterisation of antimitotic products from marine organisms that disorganise the microtubule network: Ecteinascidin 743, isohomohalichondrin-B and LL-15. Br J Cancer 1996, 73: 875-83.
70. Geldof, A.A., Mastbergen, S.C., Henrar, R.E., Faircloth, G.T. Cytotoxicity and neurocytotoxicity of new marine anticancer agents evaluated using in vitro assays. Cancer Chemother Pharmacol 1999, 44: 312-8.
71. Kruczynski, A., Hill, B.T. Vinflunine, the latest vinca alkaloid in clinical development. A review of its preclinical anticancer properties. Crit Rev Oncol Hematol 2001, 40: 159-73.
72. Etievant, C., Kruczynski, A., Barret, J.M., Tait, A.S., Kavallaris, M., Hill, B.T. Markedly diminished drug resistance-inducing properties of vinflunine (20′,20′-difluoro-3′,4′-dihydrovinorelbine) relative to vinorelbine, identified in murine and human tumour cells in vivo and in vitro. Cancer Chemother Pharmacol 2001, 48: 62-70.
73. Hill, B.T., Fiebig, H.H., Waud, W.R., Poupon, M.F., Colpaert, F., Kruczynski, A. Superior in vivo experimental antitumour activity of vinflunine, relative to vinorelbine, in a panel of human tumour xenografts. Eur J Cancer 1999, 35: 512-20.
74. Fumoleau, P. et al. Phase I clinical and pharmacokinetic trial of vinflunine, a novel fluorinated vinca alkaloid in patients with advanced solid malignancies. Clin Cancer Res 2000, 6 (Suppl.): Abst 576.
75. Hamel, E., Lin, C.M. Interactions of combretastatin, a new plant-derived antimitotic agent, with tubulin. Biochem Pharmacol 1983, 32: 3864-7.
76. Lin, C.M., Ho, H.H., Pettit, G.R., Hamel, E. Antimitotic natural products combretastatin A-4 and combretastatin A-2: Studies on the mechanism of their inhibition of the binding of colchicine to tubulin. Biochemistry 1998, 28: 6984-91.
77. Medarde, M., Ramos, A.C., Caballero, E. et al. Synthesis and anti-neoplastic activity of combretastatin analogues: Heterocombretastatins. Eur J Med Chem 1998, 33: 71-7.
78. Medarde, M., Ramos, A.C., Caballero, E. et al. Synthesis and pharmacological activity of the diarylindole derivatives. Cytotoxic agents based on combretastatins. Bioorg Med Chem Left 1999, 9: 2303-8.
79. Tozer, G.M., Prise, V.E., Wilson, J. et al. Combretastatin A-4 phosphate as a tumor vascular-targeting agent: Early effects in tumors and normal tissues. Cancer Res 1999, 59: 1626-34.
80. Tozer, G.M., Prise, V.E., Wilson, J. et al. Mechanisms associated with tumor vascular shut-down induced by combretastatin A-4 phosphate: Intravital microscopy and measurement of vascular permeability. Cancer Res 2001, 61: 6413-22.
81. Griggs, J., Metcalfe, J.C., Hesketh, R. Targeting tumour vasculature: The development of combretastatin A4. Lancet Oncol 2001, 2: 82-7.
82. Dowlati, A., Robertson, K., Cooney, M. et al. A phase I pharmacokinetic and translational study of the novel vascular targeting agent combretastatin A-4 phosphate on a single-dose intravenous schedule in patients with advanced cancer. Cancer Res 2002, 61: 3408-16.
83. Hastie, S.B. Interactions of colchicine with tubulin. Pharmacol Ther 1991, 51: 377-401.
84. Hamel, E., Ho, H.H., Kang, G.J., Lin, C.M. Cornigerine, a potent antimitotic Colchicum alkaloid of unusual structure. Interactions with tubulin. Biochem Pharmacol 1988, 37: 2445-9.
85. Shi, Q., Chen, K., Morris-Natschke, S.L., Lee, K.-H. Recent process in the development of tubulin inhibitors as antimitotic antitumor agents. Curr Pharm Design 1998, 4: 219-48.
86. Guan, J., Zhu, K.-K., Brossi, A. et al. Antitumor agents 192. Antitubulin effect and cytotoxicity of C(7)-oxygenated allocolchicinoids. Coll Czech Chem Commun 1999, 64: 217-28.
87. Fitzgerald, T.J. Molecular features of colchicine associated with antimitotic activity and inhibition of tubulin polymerisation. Biochem Pharmacol 1976, 25: 1383-87.
88. Goto, H., Yano, S., Zhang, H. et al. Activity of a new vascular targeting agent, ZD6126, in pulmonary metastases by human lung adenocarcinoma in nude mice. Cancer Res 2002, 62: 3711-5.
89. Blakey, D.C., Westwood, F.R., Walker, M. et al. Antitumor activity of the novel vascular targeting agent ZD6126 in a panel of tumor models. Clin Cancer Res 2002, 8: 1974-83.
90. Radema, S.A., Beerepoot, L.V., Witteveen, P.O., Gebbink, M.F., Wheeler, C., Voest, E.E. Clinical evaluation of the novel vascular-targeting agent, ZD6126: Assessment of toxicity and surrogate markers of vascular damage. ASCO Meeting 2002, Abst 439.
91. Gadgeel, S.M., LoRusso, P.M., Wozniak, A.J., Wheeler, C. A dose-escalation study of the novel vascular-targeting agent, ZD6126, in patients with solid tumors. ASCO Meeting 2002, Abst 438.
92. Bai, R., Pettit, G.R., Hamel, E. Dolastatin 10, a powerful cytostatic peptide derived from a marine animal. Inhibition of tubulin polymerization mediated through the vinca alkaloid binding domain. Biochem Pharmacol 1990, 39: 1941-9.
93. Pitot, H.C., McElroy, E.A. Jr., Reid, J.M. et al. Phase I trial of dolastatin-10 (NSC 376128) in patients with advanced solid tumors. Clin Cancer Res 1999, 5: 525-31.
94. Michaelson et al. A phase I clinical trial of ILX651, a dolastatin-15 analog, administered as a 30 minute intravenous infusion very other day x 3 doses every 21 day in patients with advanced solid tumors. ACSO Annual Meeting 2002, Abst 414.
95. Usui, T., Kondoh, M., Cui, C.B., Mayumi, T., Osada, H. Tryprostatin A, a specific and novel inhibitor of microtubule assembly. Biochem J 1998, 333: 543-8.
96. Combeau, C., Provost, J., Lancelin, F. et al. RPR112378 and RPR115781: Two representatives of a new family of microtubule assembly inhibitors. Mol Pharmacol 2000, 57: 553-63.
97. Bacher, G.B., Nickel, P., Emig, U. et al. D-24851, a novel synthetic tubulin inhibitor, exerts curative antitumoral activity in vivo, efficacy towards multidrug resistant tumor cells, and lacks neurotoxicity. Cancer Res 2001, 61: 392-9.
98. Beckers, T., Reissmann, T., Schmidt, M. et al. 2-Aroylindoles, a novel class of potent, orally active small molecule tubulin inhibitors. Cancer Res 2002, 62: 3113-9.
99. Mahboobi, S., Pongratz, H., Hufsky, H. et al. Synthetic 2-aroylindole derivatives as a new class of potent tubulin-inhibitory, antimitotic agents. J Med Chem 2001, 44: 4535-53.
100. Gatspar, R., Goldbrunner, M., Marko, D., Von Angerer, E. Methoxy-substituted-3-formyl-2-phenylindoles inhibit tubulin polymerization. J Med Chem 1998, 41: 4965-72.
101. Goldbrunner, M., Loidl, G., Polossek, T., Mannschreck, A., Von Angerer, E. Inhibition of tubulin polymerisation by 5,6-dihy-dro-indolo(2,1-a)isoquinoline derivatives. J Med Chem 1997, 40: 3524-33.
102. Shan, B., Medina, J.C., Santha, E. et al. Selective, covalent modification of β-tubulin residue Cys-239 by T138067, an antitumor agent with in vivo efficacy against multidrug-resistant tumors. Proc Natl Acad Sci USA 1999, 96: 5686-91.
103. Donehower, R.C., Schwartz, G., Wolf, A.C. et al. Phase I and pharmacokinetic study of T138067 administered as a weekly 3-hour infusion. NCI-WORTC-AACR Meeting 2000, Abst 564.
104. Leung, T.W., Feun, L., Posey, J., Stagg, R.J., Levy, M.D., Venook, A.P. A phase II study of T138067-sodium in patients (pts) with unresectable hepatocellular carcinoma (HCC). ASCO Meeting 2002, Abst 572.
105. Jahan, T.M., Sandler, A., Burris, H. et al. A phase II study of T138067-sodium in prior taxane-treated patients (pts) with locally advanced or metastatic non-small cell lung cancer (NSCLC). ASCO Meeting 2002, Abst 1282.
106. Koyanagi, N., Nagasu, T., Fujita, F. et al. In vivo tumor growth inhibition produced by a novel sulfonamide, E7010, against rodent and human tumors. Cancer Res 1994, 54: 1702-6.
107. Yoshimatsu, K., Yamaguchi, A., Yoshino, H., Koyanagi, N., Kitoh, K. Mechanism of action of E7010, an orally active sulfon-amide antitumor agent: Inhibition of mitosis by binding to the colchicine site of tubulin. Cancer Res 1997, 57: 3208-13.
108. Yamamoto, K., Noda, K., Yoshimura, A., Fukuoka, M., Furuse, K., Niitani, H. Phase I study of E7010. Cancer Chem Pharmacol 1998, 42: 124-34.
109. Gwalney, S.L. 2nd, Imade, H.M., Li, Q. et al. Novel sulfonate derivatives: Potent antimitotic agents. Bioorg Med Chem Lett 2001, 11: 1671-3.
110. Tahir, S.K., Han, E.K., Credo, B. et al. A-204197, a new tubulin-binding agent with antimitotic activity in tumor cell lines resistant to known microtubule inhibitors. Cancer Res 2001, 61: 5480-5.
111. Wu-Wong, J.R., Alder, J.D., Alder, L. et al. Identification and characterization of A-105972, an antineoplastic agent. Cancer Res 2001, 61: 1486-92.
112. Li, Q., Woods, K.W., Claiborne, A. et al. Synthesis and biological evaluation of 2-indolyloxazolines as a new class of tubulin polymerisation inhibitors. Discovery of A-289099 as an orally active antitumor agent. Bioorg Med Chem Lett 2002, 12: 465-9.
113. Leoni, L.M., Hamel, E., Genini, D. et al. Indanocine, a microtubule-binding indanone and a selective inducer of apoptosis in multidrug-resistant cancer cells. J Natl Cancer Inst 2000, 92: 217-24.
114. Shih, H., Deng, L., Carrera, C.J., Adachi, S., Cottam, H.B., Carson, D.A. Rational design, synthesis and structure-activity relationships of antitumor (E)-2-benzylidene-1-tetralones and (E)-2-benzylidene-1-indanones. Bioorg Med Chem Lett 2000, 10: 487-90.
115. de Ines, C., Leynadier, D., Barasoain, I. et al. Inhibition of microtubules and cell cycle arrest by a new 1-deaza-7,8-dihydropteridine antitumor drug, CI 980, and by its chiral isomer, NCS 613863. Cancer Res 1994, 54: 75-84.
116. Ryan, C.W., Shulman, K.L., Richards, J.M. et al. CI-980 in advanced melanoma and hormone refractory prostate cancer. Invest New Drugs 2000, 18: 187-91.
117. Kunschner, L.J., Fine H., Hess, K., Jaeckle, K., Kyritsis, A.P., Yung, W.K. CI-980 for the treatment of recurrent or progressive malignant gliomas: National central nervous system consortium phase I-II evaluation of CI-980. Cancer Invest 2002, 20: 948-54.
118. Thomas, J.P., Moore, T., Kraut, E.H., Balcerzak, S.P., Galloway, S., Vandre, D.D. A phase II study of CI-980 in previously untreated extensive small cell cancer: An Ohio State University phase II research consortium study. Cancer Invest 2002, 20: 192-8.
119. Whitehead, R.P., Unger, J.M., Flaherty, L.E. et al. Phase II trial of CI-980 in patients with disseminated malignant melanoma and no prior chemotherapy. A Southwest Oncology Group study. Invest New Drugs 2001, 19: 239-43.
120. Xia, Y., Yang, Z.-Y., Xia, P. et al. Antitumor agents. 211. Fluorinated 2-phenyl-4-quinolone derivatives as antimitotic antitumor agents. J Med Chem 2001, 44: 3932-6.
121. Hour, M.-J., Huang, L-J., Kuo, S.-C. et al. 6-Alkylamino- and 2,3-dihydro-3′-methoxy-2-phenyl-4-quinazolinones and related compounds: Their synthesis, cytototxicity, and inhibition of tubulin polymerisation. J Med Chem 2000, 43: 4479-87.
122. Lee, K.-H. Anticancer drug design based on plant-derived natural products. J Biomed Sci 1999, 6: 236-50.
123. Jan, S.T., Mao, C., Vassilev, A.O., Navara, C.S., Uckun, F.M. COBRA-1, a rationally-designed epoxy-THF containing compound with potent tubulin depolymerizing activity as a novel anticancer agent. Bioorg Med Chem Lett 2000, 10: 1193-7.
124. Wang, Z., Yang, D., Mohanakrishnan, A.K. et al. Synthesis of B-ring homologated estradiol analogues that modulate tubulin polymerization and microtubule stability. J Med Chem 2000, 43: 2419-29.
125. Brueggemeier, R.W., Bhat, A.S., Lovely, C.J. et al. 2-Methoxyestradiol: A new 2-methoxy estrogen analog that exhibits antiprolifeative activity and alters tubulin dynamics. J Steroid Biochem Mol Biol 2001, 145-56.
126. Reiser, F., Bernas, M., Witte, M., Witte, C. Inhibition of normal and experimental angiotumor endothelial cell proliferation and cell cycle progression by 2-methoxyestradiol. Proc Soc Exp Biol Med 1998, 219: 211-6.
127. Cushman, M., Mohanakrishnan, A.K., Hollingshead, M., Hamel, E. The effect of exchanging various substituents at the 2-position of 2-methoxyestradiol on cytotoxicity in human cancer cell cultures and inhibition of tubulin polymerisation. J Med Chem 2002, 45: 4748-54.
128. Chaudoreille, M.M., Peyrot, V., Braquer, D., Codaccioni, F., Crevat, A. Qualitative study of the interaction mechanism of estrogenic drugs with tubulin. Biochem Pharmacol 1991, 41: 685-93.
129. Altmann, K.H., Wartmann, M., O'Reilly, T. Epothilones and related structures - a new class of microtubule inhibitors with potent in vivo antitumor activity. Biochim Biophys Acta 2000, 1470: M-79-91.