PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Tytuł artykułu

Inhibitory mikrotubul w terapii przeciwnowotworowej

Identyfikatory
Warianty tytułu
EN
Inhibitors of microtubule in cancer therapy
Języki publikacji
PL
Abstrakty
EN
Microtubule targeting drugs being in the late preclinical or early clinical development are described in this article. New semisynthetic paclitaxel analogues, natural compounds of diverse structure such as epothilones, combretastatins, colchino-ids or dolastatins and synthetic compounds of low molecular weight such as heterocombretastatins, sulfonamides, phenstatins, indoles and quinolones belong to this category of anticancer medicines. Microtubules are hollow tubes consisting of L- and B-tubulin heterodimer proteins that polymerize parallelly to a cylindrical axis. The targeting of microtubules is an important mechanism in cancer chemotherapy for such drugs as the vinca alkaloids (vincristine (1), vin-blastine (la)), podophilotoxin, their semisynthetic analogues and taxanes (paclitaxel (2), docetaxel (3)) known of their great usefulness in the anticancer therapy. These agents may stabilize microtubules, as the taxanes do, or destabilize them, as it is in the case of the vinca alkaloids. Today, more than 30 compounds targeting tubulin, either stabilizing or destabilizing microtubule dynamics, are in late preclinical or early clinical development. Despite of more than 30 years after the discovery of paclitaxel microtubule inhibitors they are still of the topic of interest of all over the world. In the end of 1990 and up to 2005 year survey articles on the microtubule inhibitors were published .We expect now that the paper which presents last results study may be useful.
Rocznik
Strony
345--364
Opis fizyczny
wykr., bibliogr. 93 poz.
Twórcy
  • Katedra Chemii Organicznej, Wydział Chemiczny, Politechnika Gdańska, ul. G.Narutowicza 11/12, 80-952 Gdańsk
Bibliografia
  • [1] B.D. Hames, N.M. Hooper, Biochemia, Wydawnictwo Naukowe PWN, Warszawa, 2002.
  • [2] R. Nowak, J. Tarasiuk, Post. Biochem., 2004, 50, 330.
  • [3] K. Dzierzbicka, A.M. Kołodziejczyk, Pol. J. Chem., 2004, 78, 323.
  • [4] G.R. Pettit, M.R. Rhodes, D.L. Herald, E. Hamel, J.M. Schmidt, R.K. Pettit, J. Med. Chem., 2005, 48, 4087.
  • [5] Z. Siemion, A. Kluczyk, Peptides, 1999, 20, 647.
  • [6] K. Dzierzbicka, T. Rakowski, A.M. Kołodziejczyk, Post. Biochem., 2000, 46, 327.
  • [7] T. Beckers, S. Mahboobi, Drug Future, 2003, 28, 767.
  • [8] O.N. Zefirova, E.V. Nurieva, A.N. Ryzhov, N.V. Zyk, N.S. Zefirov, Russ. J. Org. Chem., 2005, 41, 315.
  • [9] Q. Li, H.L. Sham, S.H. Rosenberg, Ann. Rep. Med. Chem., 1999, 34, 139.
  • [10] M. Gordaliza, M.A. Castro, J.M.M. del Corral, A. San Feliciano, Curr. Pharm. Design, 2000, 6, 1811.
  • [11] P.E. Thorpe, Clin. Cancer Res., 2004, 10, 415.
  • [12] S. Honore, E. Pasquier, D. Braguer, Cell. Mol. Life Sci., 2005, 62, 3039.
  • [13] M.C. Wani, H.L. Taylor, M.E. Wall, P. Coggon, A.T. McPhail, J. Am. Chem. Soc., 1971, 93, 2325.
  • [14] R.A. Holton, C. Somoza, H.B. Kim, F. Liang, R.J. Biediger, P.D. Boatman, M. Shindo, C.C. Smith, S. Kim, H. Nadizadeh, Y. Suzuk, C. Tao, P. Vu, S. Tang, P. Zhang, K.K. Murthi, L.N. Gentile, J.H. Liu, J. Am. Chem. Soc., 1994, 116, 1597.
  • [15] R.A. Holton, H.B. Kim, C. Somoza, F. Liang, R.J. Biediger, P.D. Boatman, M. Shindo, C.C. Smith, S. Kim, H. Nadizadeh, Y. Suzuki, C. Tao, P. Vu, S. Tang, P. Zhang, K.K. Murthi, L.N. Gentile, J.H. Liu, J. Am. Chem. Soc., 1994, 116, 1599.
  • [16] P.A. Wender, N.F. Badham, S.P. Conway, P.E. Floreancig, T.E. Glass, C. Granicher, J.B. Houze, J. Janichen, D. Lee, D.G. Marquess, P.L. McGrane, W. Meng, T.P. Muccario, M. Muhlebach, M.G. Natchus, H. Paulsen, D.B. Rawlins, J. Satkofsky, A.J. Shuker, J.C. Sutton, R.E. Taylor, K. Tomooka, J. Am. Chem. Soc., 1997, 119, 2755.
  • [17] P.A. Wender, N.F. Badham, S.P. Conway, P.E. Floreancig, T.E. Glass, J.B. Houze, N.E. Krauss, D. Lee, D.G. Marquess, P.L. McGrane, W. Meng, M.G. Natchus, A.J. Shuker, J.C. Sutton, R.E. Taylor, J. Am. Chem. Soc., 1997, 119, 2757.
  • [18] T. Mukaiyama, I. Shiina, H. Iwadare, M. Saitoh, T. Nishimura, N. Ohkawa, H. Sakoh, K. Nishimura, Y. Tani, M. Hasegawa, K. Yamada, K. Saitoh, Chem. Eur. J., 1999, 5, 121.
  • [19] K.C. Nicolaou, Z. Yang, J.J. Liu, H. Ueno, P.G. Nantermet, R.K. Guy, C.F. Claiborne, J. Renaud, E.A. Couladouros, K. Paulvannan. E.J. Sorensen, Nature, 1994, 367, 630.
  • [20] K.C. Nicolaou, J.J. Liu, Z. Yang, H. Ueno, E.J. Sorenzen, C.F. Claiborne, R.K. Guy, C.-K. Hwang, M. Nakada, P.G. Nantermet, J. Am. Chem. Soc., 1995, 117, 634.
  • [21] S.J. Danishefsky, J.J. Masters, W.B. Young, J.T. Link, L.B. Snyder, T.V. Magee, D.K. Jung, R.C.A. Isaacs, W.G. Bornmann, C.A. Alalmo, C.A. Coburn, M.J. Di Grandi, J. Am. Chem. Soc., 1996, 118, 2843.
  • [22] H. Kusama, R. Hara, S. Kawahara, T. Nishimori, H. Kashima, N. Nakamura, K. Morihira, I. Kuwajima, J. Am. Chem. Soc., 2000, 122, 3811.
  • [23] D. Rodi, R. Janes, H. Sanganee, R. Holton, B. Wallace, L. Makowski, J. Mol. Biol., 1999, 285, 197.
  • [24] S.R. Olsen, Biomed. Pharmacother., 2005, 59, S306.
  • [25] M.M. Malingre, J.H. Beijnen, J.M.M. Schellens, Invest. New Drug, 2001, 19, 155.
  • [26] M. Distefano, G. Scambia, C. Ferlini, C. Gaggini, R. DeVincenzo, A. Riva, E. Bombardelli, I. Ojima, A. Fattorossi, P.B. Panoco, B.S. Mancuso, Int. J. Cancer, 1997, 72, 844.
  • [27] M.I. Nicoletti, T, Colombo, C. Rossi, C. Monardo, S. Stura, M. Zucchetti, A. Riva, P. Morazzoni, M.B. Donati, E. Bombardelli, M. D'Incalci, R. Giavazzi, Cancer Res., 2000, 60, 842.
  • [28] T.J. Altstadt, C.R. Fairchild, J. Golik, K.A. Johnston, J.F. Kadow, F.Y. Lee, B.H. Long, W.C. Rose, D.M. Vyas, H. Wong, M.J. Wu, M.D. Wittman, J. Med. Chem., 2001, 44, 4577.
  • [29] W.C. Rose, C.R. Fairchild, F.Y. Lee, Cancer Chemother. Pharmacol., 2001, 47, 97.
  • [30] M. Hidalgo, C. Aylesworth, L.A. Hammond, C.D. Britten, G. Weiss, J. Stephenson, G. Schwartz, A. Patnaik, L. Smith, K. Molpus, S. Felton, E. Gupta, K.J. Ferrante, A. Tortora, D.S. Sonnichsen, J. Skillings, E.K. Rowinsky, J. Clin. Oncol., 2001, 19, 2493.
  • [31] P. Virgnaud, P. Lejeune, M.C. Bissery, Proc. Am. Assoc. Cancer Res., 2001, 42, 1975.
  • [32] K.A. Gelmon, J. Latreille, A. Tolcher, L. Genier, B. Fisher, D. Forand, S. D'Aloisio, L. Vernillet, L. Daigneault, A. Lebecq, M. Besenval, E. Eisenhauer, J. Clin. Oncol., 2000, 18, 4098.
  • [33] M.V.N. de Souza, Quim. Nova, 2004, 27, 308.
  • [34] G. Hoefle, N. Bedorf, H. Steinmetz, G. Schomburg, K. Gerth, H. Reichenbach, Angew. Chem. Int. Ed. Engl., 1996, 35, 1567.
  • [35] R.J. Kowalski, P. Giannakakou, E. Hamel, J. Biol. Chem., 1997, 272, 2534.
  • [36] P.M. Calvert, V. O'Neill, A. Azzabi, A. Hughes, R. Plummer, C. Twelves, A. Robinson, M.A. Machan, S. Dimitrijevic, D. Moss, J. Rothermel, P. Cohen, T. Chen, A. Man, A.H. Calvert, Clin. Cancer Res., 2000, 6, 575, Suppl. S Nov.
  • [37] F.Y.F. Lee, R. Borzilleri, C.R. Fairchild, S.H. Kim, B.H. Long, C. Reventos-Suarez, G.D. Vite, W.C. Rose, R.A. Kramer, Clin. Cancer Res., 2001, 7, 1429.
  • [38] H.M. McDaid, S. Mani, H.J. Shen, F. Muggia, D. Sonnichsen, S.B. Horwitz, Clin. Cancer Res., 2002, 8, 2035.
  • [39] F. Cachoux, T. Isarno, M. Wartmann, K.H. Altmann, Chembiochem, 2006, 7, 54.
  • [40] F. Cachoux, F. Schaal, A. Teichert, T. Wagner, K.H. Altmann, Synlett, 2004, 15, 2709.
  • [41] H. Bruyere, S. Samaritani, S. Ballereau, A.Tomas, J. Royer, Synlett, 2005, 9, 1421.
  • [42] S. Chandrasekhar, V. Jagadeshwar, C. Narsihmulu, M. Sarangapani, D.R. Krishna, J. Vidyasagar, D. Vijay, G.N. Sastry, Bioorg. Med. Chem. Lett., 2004, 14, 3687.
  • [43] E. terHaar, R.J. Kowalski, E. Hamel, C.M. Lin, R.E. Longley, S.P. Gunasekera, H.S. Rosenkrauz, B.W. Day, Biochemistry, 1996, 35, 243.
  • [44] I. Paterson, G.J. Florence, K. Gerlach, J.P.Scott, N. Sereining, J. Am. Chem. Soc., 2001, 123, 9535.
  • [45] O. Loiseleur, G. Koch, J. Cercus, F. Schurch, Org. Process Res. Dev., 2005, 9, 259.
  • [46] A.B. Smith, B.S. Freeze, M.J. LaMarche, T. Hirose, I. Brouard, P.V. Rucker, M. Xian, K.F. Sundermann, S.J. Shaw, M.A. Burlingame, S.B. Horwitz, D.C. Myles, Org. Lett., 2005, 7, 311.
  • [47] L.A. Martello, H.M. McDaid, D.L. Regl, C.P.H. Yang, D.F. Meng, T.R.R. Pettus, M.D. Kaufman, A. Arimoto, S.J. Danishefsky, A.B. Smith, S.B. Horwitz, Clin. Cancer Res., 2000, 6, 1978.
  • [48] D.G. Corley, R. Herb, R.E. Moore, P.J. Scheur, V.J. Paul, J. Org. Chem., 1988, 53, 3644.
  • [49] S.L. Mooberry, G. Tien, A.H. Hernandez, A. Plubrukam, B.S. Davidson, Cancer Res., 1999, 59, 653.
  • [50] I. Paterson, C. De Savi, M. Tudge, Org. Lett., 2001, 3, 3149.
  • [51] S.L. Mooberry, D.A. Randall-Hlubek, R.M. Leal, S.G. Hegde, R.D. Hubbard, L. Zhang, P.A. Wender, P. Natl. Acad. Sci. USA, 2004, 101, 8803.
  • [52] M. Takahashi, S. Iwasaki, H. Konayashi, S. Okuda, I. Murai, Y. Sato, Biochim. Biophys. Acta, 1987, 926, 215.
  • [53] M. Eggen, G.I. Georg, Med. Res. Rev., 2002, 2, 85.
  • [54] K. Menon, E. Alvarez, P. Forler, V. Phares, T. Amsrud, C. Shih, R. Al-Awar, B.A. Teicher, Cancer Chemother. Pharmacol., 2000, 46, 142.
  • [55] O. Pagani, G. Greim, K. Weigang, K. Westphal, S. Van den Bosch, T. DePas, M. Burgess, I. Weimer, C. Sessa, Clin. Cancer Res., 1999, 5 (Suppl.), Abst 8.
  • [56] A. Kruczyński, B.T. Hill, Cri. Rev. Oncol. Hematol., 2001, 40, 159.
  • [57] B.T. Hill, H.H. Fiebig, W.R. Waud, M.F. Poupon, F. Colpaert, A. Kruczyński, Eur. J. Cancer, 1999, 35, 512.
  • [58] J. Griggs, J.C. Metcalfe, R. Hesketh, Lancet Oncol., 2001, 2, 82.
  • [59] N.H. Nam, Curr. Med. Chem., 2003, 10, 1697.
  • [60] R. LeBlanc, J. Dickson, T. Brown, M. Stewart, H.N. Pati, D. VanDerveer, H. Arman, J. Harris, W. Pennington, H.L. Holt, M. Lee, Bioorg. Med. Chem., 2005, 13, 6025.
  • [61] B. Coggiola, F. Pagliai, G. Allegrone, A.A. Genazzani, G.C. Tron, Bioorg. Med. Chem. Lett., 2005, 15, 3551.
  • [62] J. Kaffy, R.E. Pontikis, J.C. Florent, C. Monneret, Org. Biomol. Chem., 2005, 3, 2657.
  • [63] D.A. Ramirez, J.X. Zhang, K. Klausmeyer, R.R. Kane, J. Chem. Crystallogr., 2005, 35, 227.
  • [64] K. Odlo, J. Klaveness, P. Rongved, T.V. Hansen, Tetrahedron Lett., 2006, 47, 1101.
  • [65] A. Dowlati, K. Robertson, M. Cooney, W.P. Petros, M. Stratford, J. Jesberger, N. Rafie, B. Overmoyer, V. Makkar, B. Stambler, A. Taylor, J. Waas, J.S. Lewin, K.R. McCrae, S.C. Remick, Cancer Res., 2002, 61, 3408.
  • [66] C. Kanthou, O. Greco, A. Stratford, I. Cook, R. Knight, O. Benzakour, G. Tozer, Am. J. Pathol., 2004, 165, 1401.
  • [67] J.H. Bilenker, K.T. Flaherty, M. Rosen, L. Davis, M. Gallagher, J.P. Stevenson, W.J. Sun, D. Vaughn, B. Giantonio, R. Zimmer, M. Schnall, P.J. O'Dwyer, Clin. Cancer Res., 2005, 11, 1527.
  • [68] S.B. Hastie, Pharmacol. Ther., 1991, 51, 377.
  • [69] E. Hamel, H.H. Ho, G.J. Kang, C.M. Lin, Biochem. Pharmacol., 1988, 37, 2445.
  • [70] J. Guan, K.K. Zhu, A. Brossi, Y. Tachibana, K.F. Bastow, P. Verdier-Pinard, E. Hamel, A.T. McPhail, K.H. Lee, Coll. Czech. Chem. Commun., 1999, 64, 217.
  • [71] D.C. Blakey, F.R. Westwood, M. Walker, G.D. Hughes, P.D. Davis, S.E. Ashton, A.J. Ryan, Clin. Cancer Res., 2002, 8, 1974.
  • [72] R. Bai, G.R. Pettit, E. Hamel, Biochem. Pharmacol., 1990, 39, 1941.
  • [73] E.D. Saad, E.H. Kraut, P.M. Hoff, D.F. Moore, D. Jones, R. Pazdur, J.L. Abbruzzese, Am. J. Clin. Oncol., 2002, 25, 451.
  • [74] S. Ayral-Kaloustian, A. Zask, Drug Future, 2005, 30, 254.
  • [75] A. Zask, J. Kaplan, S. Musto, F. Loganzo, J. Am. Chem. Sci., 2005, 127, 17667.
  • [76] T. Usui, M. Kondoh, C.B. Cui, T. Mayumi, H. Osada, Biochem. J., 1998, 333, 543.
  • [77] C. Combeau, J. Provost, F. Lancelin, Y. Tournoux, F. Prod'homme, F. Herman, F. Lavelle, J. Leboul, M. Vuilhorgne, Mol. Pharmacol., 2000, 57, 553.
  • [78] G. Bacher, B. Nickel, P. Emig, U. Vanhoefer, S. Seeber, A. Shandra, T. Klenner, T. Beckers, Cancer Res., 2001, 62, 392.
  • [79] T. Beckers, T. Reissmann, M. Schmidt, A.M. Burger, H.H. Fiebig, U. Vanhoefer, H. Pougratz, H. Hufsky, J. Hockemeyer, M. Frieser, S. Mahboodi, Cancer Res., 2002, 62, 3113.
  • [80] R. Gatspar, M. Goldbrunner, D. Marko, E. Von Angerer, J. Med. Chem., 1998, 41, 4965.
  • [81] M. Medarde, A.C. Ramos, E. Caballero, R.P.L. de Clairac, J.L. Lopez, D.G. Gravalos, A. San Feliciano, Eur. J. Med. Chem., 1998, 33, 71.
  • [82] B. Shan, J.C. Medina, E. Santha, W.P. Frankmoelle, T.C. Chou, R.M. Learned, M.R. Narbut, D. Stott, P.G. Wu, J.C. Jaen, T. Rosen, P.B.M.W.M. Timmermaus, H. Beckmann, Proc. Natl. Acad. Sci. USA, 1999, 96, 5686.
  • [83] K. Yoshimatsu, A. Yamguchi, H. Yoshino, N. Koyanagi, K. Kitch, Cancer Res., 1997, 57, 3208.
  • [84] K. Yamamoto, K. Noda, A.Yoshimura, M. Fukuoka, K. Furuse, H. Niitani, Cancer Chem. Pharmacol., 1998, 42, 124.
  • [85] S.L. Gwaltney, H.M. Imade, Q. Li, L. Gehrke, R.B. Credo, R.B. Warner, J.Y. Lee, P. Kovar, D. Frost, S.C. Ng, H.L. Sham, Bioorg. Med. Chem. Lett., 2001, 11, 1671.
  • [86] S.K. Tahir, E.K. Han, B. Credo, H.S. Jae, J.A. Pietenpol, C.D. Scatena, J.S.R. Wu-Wong, D. Frost, H. Sham, S.H. Rosenberg, S.C. Ng, Cancer Res., 2001, 61, 5480.
  • [87] H. Shih, L. Deng, C.J. Carrera, S. Adachi, H.B. Cottam, D.A. Carson, Bioorg. Med. Chem. Lett., 2000, 10, 487.
  • [88] C. De Ines, D. Leynadier, I. Barasoain I, V. Peyrot, P. Garcia, C. Briand, G.A. Rener, C. Temple, Cancer Res., 1994, 54, 75.
  • [89] Y. Xia, Z.Y. Yang, P. Xia, T. Hackl, E. Hamel, A. Mauger, J.H. Wu, K.H. Lee, J. Med. Chem., 2001, 44, 3932.
  • [90] M. Cushman, A.K. Mohanakrishnan, M. Hollingshead, E. Ramel, J. Med. Chem., 2002, 45, 4748.
  • [91] C. Obasaju, G.R. Hudes, Hematol. Oncol. Clin. N, 2001, 15, 525.
  • [92] K.N. Weiderhold, D.A. Randall-Hiubek, L.A. Polin, E. Hamel, S.L. Mooberry, Int. J. Cancer, 2006, 118, 1032.
  • [93] A.L. Larroque, J. Dubois, S. Thoret, G. Aubert, D. Guenard, F. Gueritte, Bioorg. Med. Chem. Lett., 2005, 15, 4722.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUS2-0010-0013
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.