Kombretastatyna A-4 (CA-4) i jej analogi : synteza i aktywność biologiczna

Dzierzbicka, K.; Kubacka, P.; Renusz, S.; Kołodziejczyk, A.M.

Artykuł - szczegóły

Tytuł artykułu

Kombretastatyna A-4 (CA-4) i jej analogi : synteza i aktywność biologiczna

Autorzy

Dzierzbicka K. , Kubacka P. , Renusz S. , Kołodziejczyk A.M.

Wybrane pełne teksty z tego czasopisma

Identyfikatory

Warianty tytułu

Combretastatin A-4 (CA-4) and its analogues. synthesis and biological activity

Języki publikacji

Abstrakty

This article described synthesis and biological activity of combretastatin A-4 (CA-4) and its analogues. Combretastatin A-4 (CA-4), a natural product isolated from the South African bush willow tree Combretum caffrum, binds to the colchicine binding site and inhibits the polymerization of microtubules. CA-4 exhibits potent cytotoxicity against a variety of human cancer cell lines including multidrug-resistant (MDR) cell lines [5-7]. The studies of structure-activity relationship (SAR) of CA-4 1 (Fig. 1) showed that 3,4,5-trimethoxy substitution on the A ring and the 4'-methoxy group on the B ring and the cis-olefin configuration are crucial for potent cytotoxicity, while the 3'-hydroxy group is optional [5-7]. A many of CA-4 analogues were synthesized where the double bond have been replaced by introduction of nonheterocyclic groups (e.g. ethers, olefins, ketones, sulfonates, sulfonamides, amide derivatives, amine, cyclopentanes) or heterocyclic groups containing five-membered rings (e.g. pyrazoles, thiazoles, triazoles, tetrazoles, oxazoles, furans, dioxolanes, thiophenes) and indoles [5, 7, 41, 56] (Fig. 9-12). Up to now, many CA-4 analogues and their biological activity have been extensively studied and three derivatives are currently in clinical trials: a water-soluble disodium phosphate derivative of CA-4 (CA-4P) 11c (Fig. 3); Oxi-4503, a water-soluble combretastatin A-1 (CA-1diP) 4a (Fig. 1); and AC7700 59e (Scheme 7) an aminocombretastatin prodrug developed in Japan in 1998 [5-10, 34].

Słowa kluczowe

inhibitory mikrotubul kombretastatyna A-4 CA-4 synteza analogi CA-4 aktywność przeciwnowotworowa aktywność antymitotyczna

inhibitors of microtubule combretastatin A-4 CA-4 synthesis CA-4 analogues antitumor activity antimitotic activity

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2008

Tom

[Z] 62, 11-12

Strony

1037--1064

Opis fizyczny

bibliogr. 73 poz., wykr.

Twórcy

autor

Dzierzbicka K.

autor

Kubacka P.

autor

Renusz S.

autor

Kołodziejczyk A.M.

Katedra Chemii Organicznej, Wydział Chemiczny, Politechnika Gdańska, ul. G. Narutowicza 11/12, 80-952 Gdańsk, kd@chem.pg.gda.pl

Bibliografia

[1] R. Nowak, J. Tarasiuk, Post. Biochem., 2004, 50, 330.
[2] K. Dzierzbicka, A.M. Kołodziejczyk, Wiad. Chem., 2006, 60, 345.
[3] A. Bruce. Podstawy biologii komórki: wprowadzenie do biologii molekularnej, przekł. pod red. J. Michejda, .J. Augustyniak. Wydawnictwo Naukowe PWN, Warszawa, 1999.
[4] G.R Pettit, S.B. Singh, E. Hamel, CM. Lin, D.S. Alberts, D. Garcia-Kendall, Experiment, 1989, 45, 209.
[5] G.C. Tron, T. Pirali, G. Sorba, F. Pagliai, S. Busacca, A.A. Genazzani, J. Med. Chem., 2006, 49, 3033.
[6] K. Dzierzbicka, A.M. Kołodziej czyk, Pol. J. Chem., 2004, 78, 323.
[7] N.H. Nam, Curr. Med. Chem.. 2003,10, 1697.
[8] A. Dowlati, K. Robertson. M. Cooney, W.P. Petros, M. Stratford, J. Jesberger, N. Rafie. B. Over-moyer. V. Makkar, B. Stambler, A. Taylor, J. Waas, J.S. Lewin, K.R. McCrae, S.C. Remick, Cancer Res., 2002,61,3408.
[9] C.M.L. West, P. Price, Anti-Cancer Drug, 2004,15, 179.
[10] S.L. Young, D.J. Chaplin, Expert Opin. tnvestig. Drugs, 2004,13, 1171.
[11] G.R. Pettit, G.M. Cragg, D.L. Herald. J.M. Schmidt, P. Lohavanijaya. Can. J. Chem.. 1982, 60, 1374.
[12] G.R. Pettit, SB. Singh. G.M. Cragg, J. Org. Chem., 1985, 50, 3404.
[13] G.R. Pettit, SB. Singh, ML. Niven, E. Hamel, J.M. Schmidt, J. Nat. Prod., 1987, 50, 119.
[14] G.R. Pettit, G.M. Cragg,.S.B. Singh, J. Nat. Prod., 1987, 50, 386.
[15] G.R. Pettit, S.B. Singh. Can. J. Chem.. 1987, 65, 2390.
[16] G.R. Pettit, C. Temple. V.L. Narayanan. R. Varna, M.J. Simpson, M.R. Boyd. G.A. Rener. N. Ban-sal, Anti-Cancer Drug Design. 1995,10, 299.
[17] G.R. Pettit, J.W. Lippert, D.L. Herald, E. Hamel, R.K. Pettit, J. Nat. Prod.. 2000. 63, 969.
[18] G.R. Pettit, S.B. Singh, M.R. Boyd, E. Hamel, R.K. Pettit, J.M. Schmidt, F. Hogan, J. Med. Chem., 1995, 38, 1666.
[19] G.R. Pettit, M.R. Rhodes, D.L. Herald. E. Hamel, J.M. Schmidt, R.K. Pettit. J. Med. Chem., 2005. 48. 4087.
[20] SB. Singh. G.R. Pettit, J. Org. Chem., 1989, 54. 4105.
[21] A. Furstner, K. Nikolakis, Liebigs Ann. Chem., 1996. 2107.
[22] N.J. Lawrence, F.A. Ghani, L.A. Hepworth, J.A. Hadfield, A.T. McGown, R.G. Pritchard, Synthesis, 1999, 1656.
[23] K. Gaukroger, J.A. Hadfield. L.A. Hepworth,N.J. Lawrence, A.T. McGown, J. Org. Chem., 2001, 66,8135.
[24] A. Giraud, O. Provot. A. Hamze, J-D. Brion, M. Alami, Tetrahedron Lett., 2008, 49. 1107.
[25] G.R. Pettit, M.R. Rhodes, Anti-Cancer Drug Design, 1998,13. 183.
[26] K. Gaukroger, J.A. Hadfield, N.J. Lawrence, S. Nolan, A.T, McGown, Org. Biomol. Chem., 2003, I, 3033.
[27] G.R. Pettit, M.D. Minardi, H.J. Rosenberg, E. Hamel, M.C. Bibby, S.W. Martin, M.K. Jung, R.K. Pettit, T.J. Cuthberston, J.C. Chapuis, J. Nat. Prod., 2005, 68, 1450.
[28] R.T. Brown, B.W. Fox, J.A. Hadfield, A.T. McGown, S.P. Mayalarp, G.R. Pettit, J.A. Woods, J. Chem. Soc. Perk. T. 1, 1995, 577.
[29] S.B. Bedford, C.P. Quarterman, D.L. Rathbone, J.A. Slack, B.J. Griffin, M.F.G. Stevens, Bioorg. Med. Chem. Lett., 1996, 6, 157.
[30] J. Hua.Y. Sheng. KG. Pinney. CM. Garner. R.R. Kane. J.A. Prezioso. G.R. Pettit. D.J. Chaplin. K. Edvardsen, Anticancer Res.. 2003, 23, 1433.
[31] W. Badn. S. Kalliomaki, B. Widegren. H.O. Sjogren, Clin. Cancer Res., 2006. 12. 4714.
[32] Q.S. Ng, V. Goh, D. Carnell, K. Meer, A.R. Padhani, M.I. Saunders. P.J. Hoskin, Int. J. Radiat. Oncol., 2007, 67, 1375.
[33] B.A. Salmon, D.W. Siemann, Int. J. Radiat. Oncol., 2007, 68, 211.
[34] J.W. Lippert III, Bioorg. Med. Chem., 2007, 15, 605.
[35] S.X. Cai, Recent Pat. Anti-Cane, 2007, 2, 79.
[36] Y. Kong. J. Grembecka. M.C. Edler. E. Hamel, S.L. Mooberry. M. Sabat, J. Rieger. M.L. Brown, Chem. Biol., 2005, 12, 1007.
[37] K.G. Pinney, M.P. Mejia, V.M. Villalobos, B.E. Rosenquist, G.R. Pettit, P. Verdier-Pinard, E. Hamel, Bioorg. Med. Chem.. 2000, 8, 2417.
[38] M. Medarde, A.B. Maya,1C. Perez-Melero, J. Enzyme Inhib. Med. Chem., 2004, 19, 521.
[39] C. Perez-Melero, A.B. Maya, B. del Rey, R. Pelaez, E. Caballero, M. Medarde, Bioorg. Med. Chem. Lett., 2004. 14.3771.
[40] A.B. Maya, C. Perez-Melero, C. Mateo, D. Alonso, J.L. Fernandez, C. Gajate, F. Mollinedo, R. Pelaez, E. Caballero, M. Medarde, J. Med. Chem., 2005, 48, 556.
[41] J.P. Liou, Y.L. Chang, F.M. Kuo, C.W. Chang, H.Y. Tseng, C.C. Wang, Y.N. Yang, J.Y. Chang, S.J. Lee, H.P. Hsieh, J. Med. Chem., 2004, 47, 4247.
[42] S.L. Gwaltney, H.M. Imade, K.J. Barr, Q. Li, L. Gehrke, R.B. Credo, R.B. Warner, J.Y. Lee, P. Kovar. J.Y. Wang. MA. Nukkala. N.A. Zielinski. D. Frost. S.C. Ng, H.L. Sham. Bioorg. Med. Chem. Lett., 2001,11,871.
[43] J.A. Hadifield, K. Gaukroger, N. Hirst. A.P. Weston, N J. Lawrence, A.T. McGown, Eur. J. Med. Chem., 2005, 40, 529.
[44] K. Ohsumi K, R. Nakagawa, Y. Fukuda, T. Hatanaka, Y. Morinaga, Y. Nihei, K. Ohishi, Y. Suga, Y. Akiyama, T. Tsuji, J. Med. Chem., 1998, 41, 3022.
[45] K. Ohsumi, T. Hatanaka, R. Nagakawa, Y. Fukuda. Y. Morinaga, Y. Suga, Y. Nihei. K. Ohsini. Y. Akiyama, T. Tsuji, Anti-Cancer Drug Des., 1999, 14, 539.
[46] Y. Nihei, Y. Suga. Y. Morinaga, K. Ohishi. A. Okano, K. Ohsumi, T. Hatanaka, R. Nakagawa, T. Tsuji, Y. Akiyama, S. Saito, K. Hori, Y. Sato, T. Tsuruo , Jpn. J. Cancer Res., 1999, 90, 1016.
[47] J.P. Liou, C.W. Chang, J.S. Song, Y.N. Yang, C.F. Yeh, H.Y. Tseng, Y.K.. Lo, CM. Chang, H.P. Ksleh, J. Med. Chem., 2002, 45, 2556.
[48] H.P. Hsieh, J.P. Liou. Y.L. Chang, J.S. Song, Y.N. Yang. C.F. Yeh. H.Y. Tseng, Y.K. Lo, CM. Chang, J. Med. Chem., 2002, 45, 2556.
[49] J.P. Liou, J.Y. Chang, C.Y. Chang, N. Mahindroo, F.M. Kuo, H.P. Hsieh, J. Med. Chem., 2004,47, 2897.
[50] G.R. Pettit, B. Toki, D.I. Herald, P. Verdier-Pinard, M.R. Boyd, E. Hamel, R.K. Pettit, J. Med. Chem., 1998, 41, 1688.
[51] L. Wang, K.W. Woods. Q. Li, K.J. Barr, R.W. McCroskey, S.M. Hannick, R.B. Gherke. Y.H. Hui. K. Marsh, R. Warner, J.Y. Lee, N. Zieliński-Mozng, D. Frosi, S.H. Rosenberg, H.L. Sham, J. Med. Chem., 2002, 45, 1697.
[52] R.#Shirai, H. Takayama,A. Nishikawa, Y. Koiso, Y. Hashimoto. Bioorg. Med. Chem. Lett., 1998,8, 1997.
[53] N.J. Lawrence, E. Simon, M. Annitage, B. Greedy, D. Cook, S. Ducky, Tetrahedron Lett., 2006,47, 1637.
[54] F. Bellina, S. Cauteruccio, S. Monti, R. Rossi, Bioorg. Med. Chem. Lett., 2006, 16, 5757.
[55] D. Simoni, R. Romagnoli, R. Baruchello, R. Rondanin, M. Rizzi, M.G. Pavani, D. Alloatti, G. Giamnini, M. Marcellini, T. Riccioni, M. Castorina, M.B. Guglielmi, F. Bucci, P. Carminati, C Pisano, J. Med. Chem., 2006, 49, 3143.
[56] J.-X. Duan, X. Cai, F. Meng, L. Lan, Ch. Hart, M. Matteucci, J. Med. Chem., 2007, 50, 1001.
[57] Q. Zhang. Y. Peng. X.I. Wang, S.M. Keenan, S. Arora, W.J. Welsh, J. Med. Chem.. 2007. 50. 749.
[58] Ch.-M. Sun, L.-G. Lin, H.-J. Yu, Ch.-Y. Cheng, Y.-Ch. Tsai, Ch.-W. Chu. Y.-H. Din, Y.-P. Chau, M.-J. Don, Bioorg. Med. Chem. Lett., 2007, 17, 1078.
[59] C. Congiu, M.T. Cocco, V. Onnis, Bioorg. Med. Chem. Lett., 2008,18, 989.
[60] R. Romagnoli, P.G. Baraldi, M.D. Carrion, C. Lopez-Cara, D. Preti, F. Fruttarolo, M. G. Pavani, MA. Tabrizi, M. Tolomeo, S. Grimaudo, C. Di Antonella. J. Balzarini, J.A. Hadifield. A. Brancale. E. Hamel. J. Med. Chem., 2007. 50. 2273.
[61] R. Romagnoli, P.G. Baraldi, T. Sarkar, M.D. Carrion, C. Lopez-Cara, O. Cruz-Lopez, D. Preti, M.A. Tabrizi, M. Tolomeo, S. Grimaudo, A. Di Cristina, N. Zonta, J. Balzarini, A. Brancale, H.-P. Hsieh, E. Hamel. J. Med. Chem., 2008, 51, 1464.
[62] D. Simoni, R. Romagnoli, R. Baruchello, R. Rondanin, M. Rizzi, M.G. Pavani, D. Alloatti, G. Giannini, M. Marcellini, T. Riccioni. M. Castorina, M.B. Guglielmi, F. Bucci, P. Carminati. C. Pisano, J. Med. Chem., 2006. 49, 3143.
[63] D. Alloatti, G. Giannini, W. Cabri. I. Lustrati, M. Marzi, A. Ciacci. G. Galio, M.O. Tinti. M. Marcellini, T. Riccioni, M.B. Guglielmi, P. Carminati, C. Pisano. J. Med. Chem., 2008, 51, 2708.
[64] C. Mousset, A. Giraud, O. Provot, A. Hamze, J. Bignon, J.-M. Liu, S. Thoret, J. Dubois, J.-D. Brion, M. Alami, Bioorg. Med. Chem. Lett.. 2008,18, 3266.
[65] P. Hinnen, F.A.L.M. Eskens, Brit. J. Cancer. 2007. 96. 1159.
[66] M.J. Wu. Q.M. Sun, C.H. Yang, D.D. Chen, J. Ding. Y. Chen. L.P. Lin. Y.Y. Xie, Bioorg. Med. Chem. Lett.. 2007, 17, 869.
[67] 1. Vitale, A. Antoccia, C. Cenciarelli, P. Crateri, S. Meschini, G. Arancia, C. Pisano, C. Tanzarella, Apoptosis, 2007, 12, 155.
[68] K. Uno. T. Tanabea, T. Ogamino, R. Okada, M. Imoto, S. Nishiyama, Heterocycles, 2008, 75, 291.
[69] R. Siles, IF. Ackley, M.B. Hadimani, J.J. Hall, B.E. Mugabe, R. Guddneppanavar, K.A. Monk, J.C. Chapuis. G.R. Pettit, D..J. Chaplin, K. Edvardsen, M.L. Trawick. CM. Gamer, K.G. Pinney, J.Nat. Prod., 2008, 71,313.
[70] X. Sun, J. Zhu, C. Zhong, K.J. Izumi, C. Zhang, Chinese .J. Chem., 2007, 25, 1866.
[71] D.M. Patterson, G.J.S. Rustin, N. Serradell, E. Rosa, J. Bolos, Drugs Future, 2007, 32, 1025.
[72] F. Zhang, C. Sun, J.X. Wu, C.Y. He, X.J. Ge, W.M. Huang, Y. Zou, X.M. Chen, W. Qi, Q.W. Zhai, Pharmacol. Res.. 2008, 57, 318.
[73] C. Cenciarelli, C. Tanzarella, 1. Vitale, C. Pisano, P. Crateri, S. Meschini. G. Arancia, A. Antoccia, Apoptosis, 2008, 13, 659.

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUS5-0013-0078