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2013 | 18 | 3 |

Tytuł artykułu

Tubulin-interactive stilbene derivatives as anticancer agents

Warianty tytułu

Języki publikacji

EN

Abstrakty

EN
Microtubules are dynamic polymers that occur in eukaryotic cells and play important roles in cell division, motility, transport and signaling. They form during the process of polymerization of α- and β-tubulin dimers. Tubulin is a significant and heavily researched molecular target for anticancer drugs. Combretastatins are natural cis-stilbenes that exhibit cytotoxic properties in cultured cancer cells in vitro. Combretastatin A-4 (3′-hydroxy-3,4,4′, 5-tetramethoxy-cis-stilbene; CA-4) is a potent cytotoxic cis-stilbene that binds to β-tubulin at the colchicine-binding site and inhibits tubulin polymerization. The prodrug CA-4 phosphate is currently in clinical trials as a chemotherapeutic agent for cancer treatment. Numerous series of stilbene analogs have been studied in search of potent cytotoxic agents with the requisite tubulin-interactive properties. Microtubule-interfering agents include numerous CA-4 and transresveratrol analogs and other synthetic stilbene derivatives. Importantly, these agents are active in both tumor cells and immature endothelial cells of tumor blood vessels, where they inhibit the process of angiogenesis. Recently, computer-aided virtual screening was used to select potent tubulin-interactive compounds. This review covers the role of stilbene derivatives as a class of antitumor agents that act by targeting microtubule assembly dynamics. Additionally, we present the results of molecular modeling of their binding to specific sites on the α- and β-tubulin heterodimer. This has enabled the elucidation of the mechanism of stilbene cytotoxicity and is useful in the design of novel agents with improved anti-mitotic activity. Tubulin-interactive agents are believed to have the potential to play a significant role in the fight against cancer.

Słowa kluczowe

Wydawca

-

Rocznik

Tom

18

Numer

3

Opis fizyczny

p.368-397,fig.,ref.

Twórcy

autor
  • Department of Chemical Technology of Drugs, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznan, Poland
autor
  • Department of Chemical Technology of Drugs, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznan, Poland
autor
  • Department of Chemical Technology of Drugs, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznan, Poland

Bibliografia

  • 1.Butler, M.S. Natural products to drugs: natural product-derived compounds in clinical trials. Nat. Prod. Rep. 25 (2008) 475-516.
  • 2. Pettit, G.R., Cragg, G.M., Herald, D.L., Schmidt, J.M. and Lobavanijaya, P. Antineoplastic agents. Part 84. Isolation and structure of combretastatin. Can. J. Chem. 60 (1982) 1374-1376.
  • 3. Tron, G.C., Pirali, T., Sorba, G., Pagliai, F., Busacca, S. and Genazzani, A. Medicinal chemistry of combretastatin A-4: present and future directions. J. Med. Chem. 49 (2006) 3033-3044.
  • 4. Siemann, D.W., Chaplin, D.J. and Walicke, P.A. A review and update of the current status of the vasculature-disabling agent combretastatin-A4 phosphate (CA4P). Exp. Opin. Invest. Drugs 18 (2009) 189-197.
  • 5. Desai, A. and Mitchison, T.J. Microtubule polymerization dynamics. Ann. Rev. Cell Dev. Biol. 13 (1997) 83-117.
  • 6. Nogales, E., Wolf, S.G., and Downing, K.H. Structure of the -tubulin dimer by electron crystallography. Nature 391 (1998) 199-203.
  • 7. Mitchison, T. and Kirscher, M. Microtubule assembly nucleated by isolated centrosomes. Nature 312 (1984) 232-237.
  • 8. Wang, H.W. and Nogales, E. Nucleotide-dependent bending flexibility of tubulin regulates microtubule assembly. Nature 435 (2005) 911-915.
  • 9. Akhmanova, A., and Steinmetz, M.O. Tracking the ends: a dynamic protein network controls the fate of microtubule tips. Nat. Rev. Mol. Cell Biol. 9 (2008) 309-322.
  • 10. Kline-Smith, S.L. and Walczak, C.E. Mitotic spindle assembly and chromosome segregation: refocusing on microtubule dynamics. Mol. Cell 15 (2004) 317-327.
  • 11. Kwon, M. and Scholey, J.M. Spindle mechanics and dynamics during mitosis in Drosophila. Trends Cell Biol. 14 (2004) 194-205.
  • 12. Rieder, C.L., Davison, E.A., Jensen, L.C., Cassimeris, L. and Salomon, E.D. Oscillatory movements of monooriented chromosomes and their position relative to the spindle pole result from the ejection properties of the aster and half-spindle. J. Cell Biol. 103 (1986) 581-591.
  • 13. Higuchi, T. and Uhlmann, F. Stabilization of microtubule dynamics at anaphase onset promotes chromosome segregation. Nature 433 (2005) 171-176.
  • 14. Rieder, C.L., Schultz, A., Cole, R. and Sluder, G. Anaphase onset in vertebrate somatic cells is controlled by a checkpoint that monitors sister kinetochore attachment to the spindle. J. Cell Biol. 127 (1994) 1301-1310.
  • 15. Jordan, M.A. and Wilson, L. Microtubules as a target for anticancer drugs. Nat. Rev. Cancer 4 (2004) 253-265.
  • 16. Singh, P., Rathinasamy, K., Mohan, R. and Panda, D. Microtubule assembly dynamics: an attractive target for anticancer drugs. IUBMB Life 60 (2008) 368-375.
  • 17. Bhattacharyya, B., Panda, D., Gupta, S., and Banerjee, M. Anti-mitotic activity of colchicine and the structural basis for its interaction with tubulin. Med. Res. Rev. 28 (2008) 155-183.
  • 18. Ravelli, R.B., Gigant, B., Curmi P.A., Jourdain, I., Lachkar, S., Sobel, A. and Knossow, M. Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain. Nature 428 (2004) 198-202.
  • 19. Gigant, B., Wang, C., Ravelli, R.B.G., Roussi, F., Steinmetz, M.O., Curmi, P.A., Sobel, A. and Knossow, M. Structural basis for the regulation of tubulin by vinblastine. Nature 435 (2005) 519-522.
  • 20. Chakraborti, S., Das, L., Kapoor, N., Das, A., Dwivedi, V., Poddar, A., Chakraborti, G., Janik, M., Basu, G., Panda, D., Chakrabarti, P., Surolia, A. and Bhattacharyya, B. Curcumin recognizes a unique binding site of tubulin. J. Med. Chem. 54 (2011) 6183-6196.
  • 21. Kingston, D.G.I. Tubulin-interactive natural products as anticancer agents. J. Nat. Prod. 72 (2009) 507-515.
  • 22. Nogales, E., Wolf, S.G., Khan, I.A., Luduena, R.F. and Downing, K.H. Structure of tubulin at 6.5 Ǻ and location of the taxol-binding site. Nature 375 (1995) 424-427.
  • 23. Li, H., Wu, W.K.K., Zheng, A., Che, C.T., Yu, L., Li, Z.J., Wu, Y.C., Cheng, K.-W., Yu, J., Cho, C.H. and Wang, M. 2,3’,4,4’,5’-Pentamethoxytrans-stilbene, a resveratrol derivative, is a potent inducer of apoptosis in colon cancer cells via targeting microtubules. Biochem. Pharmacol. 78 (2009) 1224-1232.
  • 24. Goncalves, A., Braguer, D., Carles, G., Andre, N., Prevot, C. and Briand, C. Caspase-8 activation independent of CD95/CD95-L interaction during paclitaxel-induced apoptosis in human colon cancer (HT29-D4). Biochem. Pharmacol. 60 (2000) 1579-1584.
  • 25. Siemann, D.W., Bibby, M.C., Dark, G.G., Dicker, A.P., Eskens, F.A., Horsman, M.R., Marmé, D. and LoRusso, P.M. Differentiation and definition of vascular-targeted therapies. Clin. Cancer Res. 11 (2005) 416-420.
  • 26. Mason, R.P., Zhao, D., Liu, L., Trawick, M.L. and Pinney, K.G. A perspective on vascular disrupting agents that interact with tubulin: preclinical tumor imaging and biological assessment. Integr. Biol (Camb.) 3 (2011) 375-387.
  • 27. Siemann, D.W. The unique characteristics of tumor vasculature and preclinical evidence for its selective disruption by tumor-vascular disrupting agents. Cancer Treat. Rev. 37 (2011) 63-74.
  • 28. Jockowich, M.E., Suarez, F., Alegret, A., Pina, Y., Hayden, B., Cebulla, C., Feuer, W. and Murray, T.G. Mechanism of retinoblastoma tumor cell death after focal chemotherapy, radiation, and vascular targeting therapy in a mouse model. Invest. Ophthalmol. Vis. Sci. 48 (2007) 5371-5376.
  • 29. Nambu, H., Nambu, R., Melia, M. and Campochiaro, P.A. Combretastatin A-4 phosphate supresses development and induces regression of choroidal neovascularization. Invest. Ophthalmol. Vis. Sci. 44 (2003) 3650-3655.
  • 30. Ma, L., Liu, Y.L., Ma, Z.Z., Dou, H.L., Xu, J.H., Wang, J.C., Zhang, X. and Zhang, Q. Targeted treatment of choroidal neovascularization using integrinmediated sterically stabilized liposomes loaded with combretastatin A4. J. Ocul. Pharmacol. Ther. 25 (2009) 195-200.
  • 31. Pettit, G.R. and Singh, S., Antineoplastic agents. Part 130. Isolation, structure and synthesis of combretastatins A-2, A-3, and B-2. Can. J. Chem. 65 (1987) 2390-2396.
  • 32. Pettit, G.R., Singh, S.B., Niven, M.L., Hamel, E. and Schmidt, J.M. Antineoplastic agents. Part 123. Isolation, structure, and synthesis of combretastatin A-1 and B-1, potent new inhibitors of microtubule assembly, derived from Combretum caffrum. J. Nat. Prod. 50 (1987) 119-131.
  • 33. Pettit, G.R., Singh, S.B., Niven, M.L., Hamel, E., Lin, C.M., Alberts, D.S. and Garcia-Kendall, D. Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4. Experientia 45 (1989) 209-211.
  • 34. Pinney, K.G., Pettit, G.R., Trawick, M.L., Jelinek, C. and Chaplin, D.J. The discovery and development of the combretastatins. in: Anticancer Agents from Natural Products, (Cragg, G.R., Kingston, D.G.I. and Newman, D.J. Eds.) 2nd edition, CRC Press/Taylor & Francis, Boca Raton, FL, 2012, 27-63.
  • 35. Chaudhary, A., Pandeya, S.N., Kumar, P., Sharma, P., Gupta, S., Soni, N., Verma, K.K. and Bhardwaj, G. Combretastatin A-4 Analogs as Anticancer Agents. Mini-Rev. Med. Chem. 7 (2007) 1186-1205.
  • 36. Tozer, G.M., Kanthou, C., Parkins, C.S. and Hill, S.A. The biology of the combretastatins as tumour vascular targeting agents. Int. J. Exp. Pathol. 83 (2001) 21-38.
  • 37. Thorpe, E.P. Vascular targeting agents as cancer therapeutics. Clin. Cancer Res. 10 (2004) 415-427.
  • 38. Xia, Y., Yang, A.-Y., Xia, P., Bastow, K.F., Tachibana, Y., Kuo, S.-C., Hamel, E., Hacki, T. and Lee, K.-H. J. Antitumor agents. 181. Synthesis and biological evaluation of 6,7,2',3',4'-substituted-1,2,3,4-tetrahydro-2-phenyl4-quinolones as a new class of anti-mitotic antitumor agents. Med. Chem. 41 (1998) 1155-1162.
  • 39. Wu, M., Sun, Q., Yang, C., Chen, D., Ding, J., Chen, Y., Lin, L. and Xie, Y. Synthesis and activity of combretastatin A-4 analogues: 1,2,3-thiadiazoles as potent antitumor agents. Bioorg. Med. Chem. Lett. 17 (2007) 869-873.
  • 40. Sriram, M., Hall, J.J., Grohmann, N.C., Strecker, T.E., Wootton, T., Franken, A., Trawick, M.L. and Pinney, K.G. Design, synthesis and biological evaluation of dihydronaphthalene and benzosuberene analogs of the combretastatins as inhibitiors of tubulin polymerization in cancer chemotherapy. Bioorg. Med. Chem. 16 (2008) 8161-8171.
  • 41. Pettit, G.R., Toki, B.E., Herald, D.L., Boyd, M.R., Hamel, E., Pettit, R.K. and Chapuis, J.-C. J. Antineoplastic agents. 410. Asymetric hydroxylation of trans-combretastatin A-4. Med. Chem. 42 (1999) 1459-1465.
  • 42. Cai, S.X. Small molecule vascular disrupting agents: potential new drugs for cancer treatment. Recent Pat. Anticancer Drug Discov. 2 (2007) 79-101.
  • 43. Salmon, H.W. and Siemann, D.W. Effect of the second generation vascular disrupting agent OXi4503 on tumor vascularity. Clin. Cancer Res. 12 (2006) 4090-4094.
  • 44. Thomson, P., Naylor, M.A., Everett, S.A., Stratford, H.R.L., Lewis, G., Hill, S., Patel, K.B., Wardman, P. and Davis, P.D. Synthesis and biological properties of bioreductively targeted nitrothienyl prodrugs of combretastatin A-4. Mol. Cancer Ther. 5 (2006) 2886-2894.
  • 45. Calligaris, D., Verdier-Pinard, P., Devred, F., Villard, C., Braguer, D. and Lafitte, D. Microtubule targeting agents: from biophysics to proteomics. Cell. Mol. Life Sci. 67 (2010) 1089-1104.
  • 46. Griggs, J., Skepper, J.N., Smith, G.A., Brindle, K.M., Metcalfe, J.C. and Hesketh, R. Inhibition of proliferative retinopathy by the antivascular agent combretastatin A-4. Am. J. Pathol. 160 (2002) 1097-1103.
  • 47. Delmonte, A. and Sessa, C. AVE8062: A new combretastatin derivative vascular disrupting agent. Expert Opin. Investig. Drugs 18 (2009) 1541-1548.
  • 48. Kim, T.J., Ravoori, M., Landen, C.N., Kamatt, A.A., Han, L.Y., Lu, C., Lin, Y.G., Merritt, W.M., Jennings, N., Spannuth, W.A., Langley, R., Gershenson, D.M., Coleman, R.L., Kundra, V. and Sood, A.K. Antitumor and antivascular effects of AVE8062 in ovarian carcinoma. Cancer Res. 67 (2007) 9337-9345.
  • 49. Pettit, G.R., Rosenberg, H.J., Dixon, R., Knight, J.C., Hamel, E., Chapuis, J.C., Pettit, R.K., Hogan, F., Sumner, B., Ain, K.B. and Trickey-Platt, B. Antineoplastic agents. 548. Synthesis of iodo- and diiodocombstatin phosphate prodrugs. J. Nat. Prod. 75 (2012) 385-393.
  • 50. Baur, J.A. and Sinclair, D.A. Therapeutic potential of resveratrol: the in vivo evidence. Nat. Rev. Drug Discov. 5 (2006) 493-506.
  • 51. Szekeres, T., Fritzer-Szekeres, M., Saiko, P. and Jaeger, W. Resveratrol and resveratrol analogues – structure-activity relationship. Pharm. Res. 27 (2010) 1042-1048.
  • 52. Schneider, Y., Chabert, P., Stutzmann, J., Coelho, D., Fougerousse, A., Gosse, F. Launay, J.-F., Brouillard, R. and Raul, F. Resveratrol analog (Z)- 3,5,4’-trimethoxystilbene is a potent anti-mitotic drug inhibiting tubulin polymerization. Int. J. Cancer 107 (2003) 189-196.
  • 53. Mazué, F., Colin, D., Gobbo, J., Wegner, M., Rescifina, A., Spatafora, C., Fasseur, D., Delmas, D., Meunier, P., Triangli, C. and Latruffe, N. Structural determinants of resveratrol for cell proliferation inhibition potency. Experimental and docking studies of new analogs. Eur. J. Med. Chem. 45 (2010) 2972-2980.
  • 54. Sale, S., Verschoyle, R.D., Boockock, D., Jones, D.J.N., Wilsher, N., Potter, G.A., Farmer, P.B., Steward, W.P. and Gescher, A.J. Pharmacokinetics in mice and growth-inhibitory properties of the putative cancer chemopreventive agent resveratrol and the synthetic analogue trans-3,4,5,4’- tetramethoxystilbene. Br. J. Cancer 90 (2004) 736-744.
  • 55. Sale, S., Tunstall, R.G., Ruparelia, K.C., Potter, G.A., Steward, W.P. and Gescher, A.J. Comparison of the effects of the chemopreventive agent resveratrol and its synthetic analog trans-3,4,5,4’-tetramethoxystilbene (DMU-212) on adenoma development in the ApcMin+ mouse and cyclooxygenase-2 in human-derived colon cancer cells. Int. J. Cancer 115 (2005) 194-201.
  • 56. Ma, Z., Molavi, O., Haddadi, A., Lai, R., Gossage, R.A. and Lavasanifar, A. Resveratrol analog trans 3,4,5,4’-tetramethoxystilbene (DMU-212) mediates antitumor effects via mechanism different from that of resveratrol. Cancer Chemother. Pharmacol. 63 (2008) 27-35.
  • 57. Park, H., Aiyar, S.E., Fan, P., Wang, J., Yue, W., Okouneva, T., Cox, C., Jordan, M.A., Demers, L., Cho, H., Kim, S., Song, R.X.-D. and Santen, R.J. Effects of tetramethoxystilbene on hormone-resistant breast cancer cells: biological and biochemical mechanisms of action. Cancer Res. 67 (2007) 5717-5726.
  • 58. Li, H., Wu, W.K.K., Li, Z.J., Chan, K.M., Wong, C.C.M., Ye, C.G., Yu, L., Sung, J.J.Y., Cho, C.H. and Wang, M. 2,3’,4,4’,5’-Pentamethoxy-transstilbene, a resveratrol derivative, inhibits colitis-associated colorectal carcinogenesis in mice. Br. J. Pharmacol. 160 (2010) 1352-1361.
  • 59. Hsieh, H.P., Liou, J.P. and Mahindroo, N. Pharmaceutical design of antimitotic agents on combretastatins. Curr. Pharm. Des. 11 (2005) 1655-1677.
  • 60. Hall, J.J., Sriram, M., Strecker, T.E., Tidmore, J.K., Jelinek, C.J., Kumar, G.D.K., Hadimani, M.B., Pettit, G.R., Chaplin, D.J., Trawick, M.L. and Pinney, K.G. Design, synthesis, biochemical, and biological evaluation of nitrogencontaining trifluoro structural modifications of combretastatin A-4. Bioorg. Med. Chem. Lett. 18 (2008) 5146-5149.
  • 61. Dyrager, C., Wickström, M., Fridén-Saxin, M., Friberg, A., Dahlén, K., Wallén, E.A.A., Gullbo, J., Grøtli, M. and Luthman, K. Inhibitors and promoters of tubulin polymerization: synthesis and biological evaluation of chalcones and related dienones as potential anticancer agents. Bioorg. Med. Chem. 19 (2011) 2659-2665.
  • 62. Cai, Y.-C., Zou, Y., Ye, Y.-L., Sun, H.-Y., Su, Q.-G., Wang, Z.-X., Zeng, Z.-L. and Xian L.-J. Anti-tumor activity and mechanisms of a novel vascular disrupting agent, (Z)-3,4’,5-trimethoxylstilbene-3’-O-phosphate disodium (M410). Invest. New Drugs 29 (2011) 300-311.
  • 63. Hatanaka, T., Fujita, K., Ohsumi, K., Nakagawa, R., Fukuda, Y., Nihei, Y., Suga,Y., Akiyama, Y. and Tsuji, T. Novel B-ring modified combretastatin analogues: syntheses and antineoplastic activity. Bioorg. Med. Chem. Lett. 8 (1998) 3371-3374.
  • 64. Cushman, M., Nagarathnam, D., Gopal, D., Chakraborti, A.K., Lin, C.M. and Hamel, E. Synthesis and evaluation of analogues of (Z)-l-(4- methoxyphenyl)-2-(3,4,5 trimethoxyphenyl)ethene as potential cytotoxic and anti-mitotic agents. J. Med. Chem. 35 (1992) 2293-2360.
  • 65. Pinney, K.G., Meija, M.P., Villalobos, V.M., Rosenquist, B.E., Pettit, G.R., Verdier-Pinard, P. and Hamel, E. Synthesis and biological evaluation of aryl azide derivatives of combretastatin A-4 as molecular probes for tubulin. Bioorg. Med. Chem. 8 (2000) 2417-2425.
  • 66. Monk, K.A., Siles, R., Hadimani, M.B., Mugabe, B.E., Ackley, J.F., Studerus, S.W., Edvardsen, K., Trawick, M.L., Garner, C.M., Rhodes, M.R., Pettit, G.R. and Pinney, K.G. Design, synthesis, and biological evaluation of combretastatin nitrogen-containing derivatives as inhibitors of tubulin assembly and vascular disrupting agents. Bioorg. Med. Chem. 14 (2006) 3231-3244.
  • 67. Wang, L., Woods, K.W., Li, Q., Barr, K.J., McCroskey, R.W., Hannick, S.M., Gherke, L., Credo, R.B., Hui, Y.H., Marsh, K, Warner, R., Lee, J.Y., Zielinski-Mozng, N., Frost, D., Rosenberg, S.H. and Sham, H.L. Potent, orally active heterocycle-based combretastatin A-4 analogues: synthesis, structure-activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation. J. Med. Chem. 45 (2002) 1697-1711.
  • 68. Schobert, R., Biersack, B., Dietrich, A., Effenberger-Neidnicht, K., Knauer, S. and Mueller, T. 4-(3-Halo/amino-4,5-dimethoxyphenyl)-5-aryloxazoles and N-methylimidazoles that are cytotoxic against combretastatin A resistant tumor cells and vascular disrupting in a cisplatin resistant germ cell tumor model. J. Med. Chem. 53 (2010) 6595-6602.
  • 69. Bonezzi, K., Taraboletti, G., Borsotti, P., Bellina, F., Rossi, R. and Giavazzi, R. Vascular disrupting activity of tubulin-binding 1,5-diaryl-1H-imidazoles. J. Med. Chem. 52 (2009) 7906-7910.
  • 70. Ohsumi, K., Hatanaka, T., Fujita, K., Nakagawa, R., Fukuda, Y., Nihei, Y., Suga, Y., Morinaga, Y., Akiyama, Y. and Tsuji, T. Syntheses and antitumor activity of cis-restricted combretastatins: 5-membered heterocyclic analogues. Bioorg. Med. Chem. Lett. 8 (1998) 3153-3158.
  • 71. Romagnoli, R., Baraldi, P.G., Brancale, A., Ricci, A., Hamel, E., Bortolozzi, R., Basso, G. and Viola, G. Convergent synthesis and biological evaluation of 2-amino-4-(3’,4’,5’-trimethoxyphenyl)-5-aryl thiazoles as microtubule targeting agents. J. Med. Chem. 54 (2011) 5144-5153.
  • 72. Romagnoli, R., Baraldi, P.G., Salvador, M.K., Camacho, M.E., Preti, D., Tabrizi, M.A., Bassetto, M., Brancale, A., Hamel, E., Bortolozzi, R., Basso, G. and Viola, G. Synthesis and biological evaluation of 2-substituted-4- (3’,4’,5’-trimethoxyphenyl)-5-aryl thiazoles as anticancer agents. Bioorg. Med. Chem. 20 (2012) 7083-7094.
  • 73. Tron, G.C., Pagliai, F., Sel Grosso, E., Genazzani, A.A. and Sorba, G. Synthesis and cytotoxic evaluation of combretafurazans. J. Med. Chem. 48 (2005) 3260-3258.
  • 74. Pirali, T., Busacca, S., Beltrami, L., Imovilli, D., Pagliali, F., Miglio, G., Massarotti, A., Verotta, L., Tron, G.C., Sorba, G. and Genazzani, A.A. Synthesis and cytotoxic evaluation of combretafurans, potential scaffolds for dual action of antitumoral agents. J. Med. Chem. 49 (2006) 5372-5376.
  • 75. Theeramunkong, S., Caldarelli, A., Massarotti, A., Aprile, S., Caprioglio, S., Zaninetti, R., Teruggi, A., Pirali, T., Grosa, G. and Tron, G.C. Regioselective Suzuki coupling of dihaloheteroaromatic compounds as a rapid strategy to synthesize potent rigid combretastatin analogues. J. Med. Chem. 54 (2011) 4977-4986.
  • 76. Zhang, W., Yang, Q., Wu, Y., Wu, L., Li, W., Qiao, F., Bao, K. and Zhang, L. Preparation of 2,3-diarylthiophene derivatives as antitumor agents. CN patent 101429189, 2009.
  • 77. Qiao, F., Zuo, D., Shen, X., Qi, H., Wang, H., Zhang, W. and Wu, Y. DAT230, a novel microtubule inhibitor, exhibits potent anti-tumor activity by inducing G2/M phase arrest, apoptosis in vitro and perfusion decrease in vivo to HT-1080. Cancer Chemother. Pharmacol. 70 (2012) 259-270.
  • 78. Liu, T., Dong, X., Xue, N., Wu, R., He, Q., Yang, B. and Hu, Y. Synthesis and biological evaluation of 3,4-biaryl-5-aminoisoxazole derivatives. Bioorg. Med. Chem. 17 (2009) 6279-6285.
  • 79. Sun, C.-N., Lin, L.-G., Yu, H.-J., Cheng, C.-Y. and Tsai, Y.-C. Synthesis and cytotoxic activities of 4,5-diarylisoxazoles. Bioorg. Med. Chem. Lett. 17 (2007) 1078-1081.
  • 80. Schobert, R., Effenberger-Neidnicht, K. and Biersack, B. Stable combretastatin A-4 analogues with sub-nanomolar efficacy against chemoresistant HT-29 cells. Int. J. Clin. Pharmacol. Ther. 49 (2011) 71-72.
  • 81. Biersack, B., Effenberger, K., Schobert, R. and Ocker, M. Oxazole-bridged combretastatin A analogues with improved anticancer properties. ChemMedChem. 3 (2010) 420-427.
  • 82. Akselsen, O.W., Odlo, K., Cheng, J-J., Maccari, G., Botta, M. and Hansen, T.V. Synthesis, biological evaluation and molecular modeling of 1,2,3-triazole analogs of combretastatin A-1. Bioorg. Med. Chem. 20 (2012) 234-242.
  • 83. Romagnoli, R., Baraldi, P.G., Cruz-Lopez, O., Lopez-Cara, C., Carrion, M.D., Brancale, A., Hamel, E., Chen, L., Bortolozzi, R., Basso, G. and Viola, G. Synthesis and antitumor activity of 1,5-disubstituted 1,2,4-triazoles as cisrestricted combretastatin analogs. J. Med. Chem. 53 (2010) 4248-4258.
  • 84. Odlo, K., Hentzen, J., Fournier dit Chabert, J., Ducki, S., Gani, O.A.B.S.M., Sylte, I., Skrede, M., Flørenes, V.A. and Hansen, T.V. 1,5-disubstituted 1,2,3-triazoles as cis-restricted analogues of combretastatin A-4: synthesis, molecular modeling and evaluation as cytotoxic agents and inhibitors of tubulin. Bioorg. Med. Chem. 16 (2008) 4829-4838.
  • 85. Odlo, K., Fournier-Dit-Chabert, J., Ducki, S., Gani, O.A.B.S.M., Sylte, I. and Hansen, T.V. 1,2,3-Triazole analogs of combretastatin A-4 as potential microtubule-binding agents. Bioorg. Med. Chem. 18 (2010) 6874-6885.
  • 86. Romagnoli, R., Baraldi, P.G., Salvador, M.K., Preti, D., Tabrizi, M.D., Brancale, A., Fu, X.H., Li, J., Zhang, S.Z., Hamel, E., Bortolozzi, R., Basso, G. and Viola, G. Synthesis and evaluation of 1,5-disubstituted tetrazoles as rigid analogues of combretastatin A-4 with potent antiproliferative and antitumor activity. J. Med. Chem. 54 (2012) 475-488.
  • 87. Shirai, R., Takayama, H., Nishikawa, A., Koiso, Y. and Hashimoto, Y. Asymetric synthesis of anti-mitotic combretadioxolane with potent antitumor activity against multi-drug resistant cells. Bioorg. Med. Chem. Lett. 8 (1998) 1997-2000.
  • 88. Pettit, R.K., Pettit, G.R., Hamel, E., Hogan, F., Moser, B.R., Wolf, S., Pon, S., Chapuis, J-C. and Schmidt, J.M. E-combretastatin and E-resveratrol structural modifications: Antimicrobial and cancer cell growth inhibitory -E-nitrostyrenes. Bioorg. Med. Chem. 17 (2009) 6606-6612.
  • 89. Dark, G.G., Hill, S.A., Prise, V.E., Tozer, G.M., Pettit, G.R. and Chaplin, D.J. Combretastatin A-4, an agent that displays potent and selective toxicity toward tumor vasculature. Cancer Res. 57 (1997) 1829-1834.
  • 90. Hori, K., Saito, S., Nihei, Y., Suzuki, M. and Sato, Y. Antitumor effects due to irreversible stoppage of tumor tissue blood flow: evaluation of a novel combretastatin A-4 derivative, AC7700. Jpn. J. Cancer Res. 90 (1999) 1026-1038.
  • 91. Sheng, Y., Hua, J., Pinney, K.G., Garner, C.M., Kane, R.R., Prezioso, J.A., Chaplin, D.J and Edvardsen, K. Combretastatin family member OXI4503 induces tumor vascular collapse through the induction of endothelial apoptosis. Int. J. Cancer 111 (2004) 604-610.
  • 92. Clémenson, C., Jouannot, E., Merino-Trigo, A., Rubin-Carrez, C. and Deutsch, E. The vascular disrupting agent ombrabulin (AVE8062) enhances the efficacy of standard therapies in head and neck squamous cell carcinoma xenograft models. Invest. New Drugs 31 (2013) 273-284.
  • 93. Rajak, H., Dewangan, P.K., Patel, V., Jain, D.K., Singh, A., Veerasamy, R., Sharma, P.C. and Dixit, A. Design of combretastatin A-4 analogs as tubulin targeted vascular disrupting agent with special emphasis on their cisrestricted isomers. Curr. Pharm. Des. 19 (2013) 1923-1955.
  • 94. Brakenhielm, E., Cao, R. and Cao, Y. Suppression of angiogenesis, tumor growth and wound healing by resveratrol, a natural compound in red wine and grapes. FASEB J. 15 (2001) 1798-1800.
  • 95. Tseng, S.H., Lin, S.M., Chen, J.C., Su, Y.H., Huang, H.Y., Chen, C.K., Lin, P.Y. and Chen, Y. Resveratrol suppresses the angiogenesis and tumor growth of gliomas in rats. Clin. Cancer Res. 10 (2004) 2190-2202.
  • 96. Kundu, J.K. and Surh, Y.-J. Cancer chemopreventive and therapeutic potential of resveratrol: mechanistic perspectives. Cancer Lett. 269 (2008) 243-261.
  • 97. Belleri, M., Ribatti, D., Nicoli, S., Cotelli, F., Forti, L., Vannini, V., Stivala, L.A. and Presta, M. Antiangiogenic and vascular-targeting activity of the microtubule-destabilizing trans-resveratrol derivative 3,5,4’-trimethoxystilbene. Mol. Pharmacol. 67 (2005) 1451-1459.
  • 98. Alex, D., Leon, E.C., Zhang, Z.-J., Yan, G.T.H., Cheng, S.H., Leong, C.-W., Li, Z.-H., Lam, K.-H., Chan, S.-W. and Lee, S.M.-Y. Resveratrol derivative, trans-3,5,4’-trimethoxystilbene, exerts antiangiogenic and vasculardisrupting effects in zebrafish through the downregulation of VEGFR2 and cell-cycle modulation. J. Cell. Biochem. 109 (2010) 339-346.
  • 99. Folkes, L.K., Christlieb, M., Madej, E., Stratford, M.R.L. and Wardman, P. Oxidative metabolism of combretastatin A-1 produces quinone intermediates with the potential to bind to nucleophiles and to enhance oxidative stress via free radicals. Chem. Res. Toxicol. 20 (2007) 1885-1894.
  • 100. Rice, L., Pampo, C., Lepler, S., Rojiani, A.M. and Siemann, D.W. Support of a free radical mechanism for enhanced antitumor efficacy of the microtubule disruptor OXi4503. Microvasc. Res. 81 (2011) 44-51.
  • 101. Madlambayan, G.J., Meacham, A.M., Hosaka, K., Mir, S., Jorgensen, M., Scott, E.W., Siemann, D.W. and Cogle, C.R. Leukemia regression by vascular disruption and anti-angiogenic therapy. Blood 116 (2010) 1539-1547.
  • 102. Peláez, R., López, J.L. and Medarde, M. Application of chemoinformatic tools for the analysis of virtual screening studies of tubulin inhibitors. Advances in Soft Computing 44 (2007) 411-441.
  • 103. Nguyen, T.L., McGrath, C., Hermone, A.R., Burnett, C.J., Zharevitz, D.W., Day, B.W., Wipf, P., Hamel, E. and Gussio, R. A common pharmacophore for a diverse set of colchicine site inhibitors using a structure-based approach. J. Med. Chem. 48 (2005) 6107-6116.
  • 104. Massarotti, A., Theeramunkong, S., Mesenzani, O., Caldarelli, A., Genazzani, A.A. and Tron, G.C. Identification of novel antitubulin agents by using a virtual screening approach based on 7-point pharmacophore model of the tubulin colchicine site. Chem. Biol. Drug Des. 78 (2011) 913-922.
  • 105. Kim, N.D., Park, E.-S., Kim, Y.H., Moon, S.K., Lee, S. S., Ahn, S.K., Yu, D.-Y., No, K.T. and Kim, K.-H. Structure-based virtual screening of novel tubulin inhibitors and their characterization as anti-mitotic agents. Bioorg. Med. Chem. 18 (2010) 7092-7100.
  • 106. Massarotti, A., Coluccia, A., Silvestri, R., Sorba, G. and Brancale, A. The tubulin colchicine domain: a molecular modeling perspective. Chem. Med. Chem. 7 (2012) 33-42.
  • 107. Romagnoli, R., Baraldi, P.G., Carrion, M.D., Cruz-Lopez, O., Cara, C.L., Tolomeo, M., Grimaudo, S., Di Cristina, A., Pipitone, M.R., Balzarini, J., Kandil, S., Brancale, A., Srkar, T. and Hamel, E. Synthesis and biological evaluation of 2-amino-3-(3’,4’,5’-trimethoxybenzoyl)-6-substituted-4,5,6,7- tetrahydrothieno[2,3-c]pyridine derivatives as anti-mitotic agents and inhibitors of tubulin polymerization. Bioorg. Med. Chem. Lett. 18 (2008) 5041-5045.
  • 108. Ruan, B.-F., Lu, X., Tang, J.-F., Wei, Y., Wang, X.-L., Zhang, Y.-B., Wang, L.-S. and Zhu, H.-L. Synthesis, biological evaluation, and molecular docking studies of resveratrol derivatives possessing chalcone moiety as potential antitubulin agents. Bioorg. Med. Chem. 19 (2011) 2688-2695.
  • 109. Kim, S., Min, S.Y., Lee, S.K., Cho, W.-J. Comparative molecular field analysis study of stilbene derivatives active against A549 lung carcinoma. Chem. Pharm. Bull. 51 (2003) 516-521.
  • 110. Chiang, Y.K., Kuo, C.C., Wu, Y.S., Chen, C.T., Coumar, M.S., Wu, J.S., Hsieh, H.P., Chang, C.Y., Jseng, H.Y., Wu, M.H., Leou, J.S., Song, J.S., Chang, J.Y., Lyu, P.C., Chao, Y.S. and Wu, S.Y. Generation of ligandbased pharmacophore model and virtual screening for identification of tubulin inhibitors with potent anticancer activity. J. Med. Chem. 52 (2009) 4221-4233.
  • 111. Tseng, C.Y., Mane, J.Y., Winter, P., Johnson, L., Huzil, T., Izbicka, E., Luduena, R.F. and Tuszynski, J.A. Quantitative analysis of the effect of tubulin isotype expression on sensitivity of cancer cell lines to a set of novel colchicine derivatives. Mol. Cancer 30 (2010) 131-150.
  • 112. Tuszynski, J.A., Craddock, T.J., Mane, J.Y., Barakat, K., Tseng, C.Y., Gajewski, M., Winter, P., Alisaraie, L., Patterson, J., Carpenter, E., Wang, W., Deyholos, M.K., Li, L., Sun, X., Zhang, Y. and Wong, G.K. Modeling the yew tree tubulin and a comparison of its interaction with Paclitaxel to human tubulin. Pharm. Res. 29 (2012) 3007-3021.

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