Ekstaza i udręka, czyli o chemii taksolu

Kacprzak, K.

Artykuł - szczegóły

Tytuł artykułu

Ekstaza i udręka, czyli o chemii taksolu

Autorzy

Kacprzak K.

Wybrane pełne teksty z tego czasopisma

Identyfikatory

Warianty tytułu

The story of taxol : ecstasy and torment

Języki publikacji

Abstrakty

Taxol (1), highly functionalised complex diterpenoid originally derived from the bark of Pacific yew, has received in recent decade wide attention of scientists in all fields of life sciences and chemistry, after the discovery of its strong and unique anticancer properties. Fast and spectracular career of this molecule is a subject of the present review. The Jarge scale of research on taxol is the consequence of public and commercial response to successful treatment of various cancer diseases and impossibility of solving basic technological and intellectual problems such as: production, drug formulation, structure-activity relationship elucidation. The discussion is divided into following sections: 1. Activity and pharmacological phenomena of taxol. 2. Production of taxol by biotechnological and chemical methods, including synthesis of taxol side chain. 3. Structure-activity relationship (SAR) of taxoids. After Horwitz reported in 1979 a strongly antimitotic activity of taxol, interest in developing the pharmacology and biochemistry of this class of natural products increased. Taxol molecule promotes anticancer activity by enhancing polymerization of tubulin and stabilization of microtubules. This process has the effect of inhibiting the normal dynamic reorganization of the cytoskeleton (with consists of microtubules) that is necessary for interphase and cell division in mitosis. Taxol and taxotere are successfully used for the treatment of a variety of cancers, in particular ovarian and breast cancer. The biggest problem hindering wider application of this drug is its limited availability from natural sources. One kg of Taxus brevifolia bark yields only 100-170 mg of taxol, after long and complicated extraction procedure. Since the yew is slow growing species this method of obtaining the drug is controvertible and unprofitable. An alternative source of taxol is semisynthesis, where natural precursor of taxol 10-deacetylbaccatin (10-DAB) can be extracted from regenerable twigs of popular yew Taxus baccata and after coupling with synthetically prepared side chain can be converted to taxol or taxotere. Taxol has also been prepared by a number of total syntheses but none of these is expected to enter the phase of commercial production. Biotechnological approaches to production by tissue culture or fungi cultivation have been reprted. Studies in the area of taxoids structure-activity relationships have first demonstrated two basic principles. The so-called 'southern' substituents, such as C-2 benzoate and the side chain, are crucial for the activity. 'Northern' substituents at C-7, C-9 and C-10 can be changed without drastic effect on the activity. The role of the substituents at C-1, the oxetane ring and diterpenoid core modifications are less well understood. There are many reports of significant activity of highly transformed taxoids, including those with: modified ABC core, open C-ring structure and aromatic C-ring. These results indicate the possibility of obtaining a synthetic, structurally simplified variant of taxol.

Słowa kluczowe

taksol taksoidy terapia antynowotworowa produkcja taksolu

taxol anticancer production of taxol

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

1998

Tom

[Z] 52, 11-12

Strony

843--870

Opis fizyczny

Bibliogr. 97 poz., schem.

Twórcy

autor

Kacprzak K.

Zakład Chemii Produktów Naturalnych, Wydział Chemii UAM ul. Grunwaldzka 6, 60-780 Poznań

Bibliografia

[1] E. Frei, Science, 1982, 217, 60.
[2] M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggen, A. T. McPhail, J. Am. Chem. Soc., 1971, 93, 2325.
[3] S. B. Horwitz, I. Fant, P. B. Schiff, Naturę (London) 1979, 277, 665.
[4] Podstawy cytofizjologii, red. K. Ostrowski, J. Kawiak, PZWL, Warszawa 1990 s. 103, 173.
[5] L. Wessjohann, Angew. Chem. Int. Ed. Engl., 1997, 36, 715.
[6] K. C. Nicolaou, W. M. Dai, R. K. Guy, Ang. Chem. Int. Ed. Engk, 1994, 33, 15, rozdz. 2 i referencje tam cytowane.
[7] H. Lataste, V. Senilh, M. Wright, D. Guenard, P. Potier, Proc. Natl. Acad. Sci. UST* 1984, 81, 4090.
[8] Farmakologia kliniczna, red. A. Chodero, Z. S. Herman, PZWL, Warszawa 1997.
[9] M. L. Rodriguez, P. Carter, C. Writh, S. Mullins, A. Lee, B. K. Blackburn, Che ry and Biology, 1995, 2, 223.
[10] E. K. Rowinsky, L. A. Cazenave, R. C. Danehower, J. Natl. Cancer. Inst., 1990,8"
[11] F. A. Holmes, R. S. Walters, R. L. Theriault, A. D. Fcrman, L. K. N M. N. Raber, A. V. Buzor, D. K. Frye, G. N. Hortobagyi, ibid., 1991, 82
[12] G. Appendino, Nat. Prod. Rep. 1995, 12, 349.
[13] J. Kobayashi, A. Ogiwara, H. Hosoyoma, H. Shigemori, N. Yoshida, T. Suasaki, Y. Li, S. Iwasaki, M. Naito, T. Tsuruo, Tetrahedron, 1994, 50, 7401.
[14] Y. Boulanger, A. Khiat, Z. H. Zhou, G. Caron, O. Zamir, ibid., 1996, 52, 8957.
[15] X. Wang, H. Shigemori, J. Kabajashi, ibid., 1996, 52, 12159.
[16] A. E. Koepp, M. Hezari, J. Zajicek, B. Vogel, R. E. LaFever, G. N. Lewis, R. Croteau, J. Biol. Chem., 1995, 270, 8686.
[17] M. R. Wildung, R. Croteau, ibid., 1996, 271, 9201.
[18] J. Hefner, S. M. Rubenstein, R. E. B. Ketchum, D. M. Gibson, R. M. Wiliams, R. Croteau, Chem. Biol., 1996, 3,479; S. M. Rubenstein, R. M. Wiliams, J. Org. Chem., 1995, 60, 7215.
[19] J. Rohr, Ang. Chem. Int. Eng. Ed., 1997, 36, 2190.
[20] T. Walle, G. N. Kumar, J. M. McMillian, K. R. Thornburg, U. K. Walle, Biochem. Pharmacol., 1993, 46, 1661.
[21] J. W. Harris, A. Katki, L. W. Anderson, G. M. Chmurny, J. V. Paukstelis, J. M. Collins, J. Med. Chem., 1994, 37, 706.
[22] S. Hu, D. Sun, X. Tian, Q. Fang, Tetrahedron Lett., 1997, 38, 2721.
[23] S. Hu, X. T. Zhu, Q. Fang, Tetrahedron, 1996, 52, 8739.
[24] A. Stierle, G. Strobel, G. Stierle, Science, 1993, 260, 214.
[25] J. S. Dahiya, (Novopharm Ltd) WO 9632490 Al 1996, (Chem. Abstr. 1996, 125, 326547).
[26] http://ponderosa-pine.uoregon.edu/Bizzo/sroka/EnvironmentalDebate.
[27] A. A. Christen, D. M. Gibson, L Blaud, US Patent 5019504 1982; S. M. Edgington, Biotechnology, 1991, 9, 933.
[28] A. G. Fett-Neto, F. DiCosmo, W. F. Reynold, K. Sakata, ibid., 1992, 10, 1572.
[29] Y. Yukimune, Nature Biotechnology, 1996, 14, 1129.
[30] http://www.eng.nsf.gov.
[31] R. J. Smith, T. L. Adams, C. R. Barton, R. W. Stahlhut, (Escagenetics Inc.) USA Pat. PTC Int. Appl. WO 93 10,253 (Chem. Abstr. 1993, 119, 26860).
[32] M. Colin, D. Guenard, F. Gueritte-Voegelein, P. Potier, US-A 4924012, 1991.
[33] D. Guenard, F. Gueritte-Voegelein, P. Potier, Acc. Chem. Res., 1993, 26, 160.
[34] F. Gueritte-Voegelein, D. Guenard, M. T. LeGoff, L. Maintagal, P. Potier, J. Med. Chem., 1991, 34, 992.
[35] J. Kant, The Chemistry of the Taxol Side Chain: Synthesis, Modifications and Conformational Studies, [w:] The Chemistry and Pharmacology of Taxol and its Derivatives, red. V. Farina Elsevier 1995.
[36] A. Commercon, D. Bezard, F. Bernard, I. D. Bourzal, Tetrahedron Lett., 1992, 33, 5185.
[37] G. Ashok, A. G. Chaudhary, D. G. I. Kingston, ibid., 1993, 34, 4921.
[38] R. Johnston, E. G. Nidy, P. J. Dobrowolski, 1. Gebhard, S. J. Qualls, N. A. Wic- nienski, R. C. Kelly, ibid., 1994, 35, 7893.
[39] R. Marder, L. Bricard, J. Dudois, D. Guenard, F. Gueritte-Voegelein, ibid., 1996, 37, 1777.
[40] D. G. I. Kingston, A. G. Chaudhary, L. A. A. Guatilaka, M. L. Middleton, ibid., 1994, 35, -4883.
[41] D. M. Bou, Y. C. Lin, C. S. Chen, J. Org. Chem., 1994, 58, 1287.
[42] S. H. Chen, V. Farina, D. M. Vyas, T. W. Doyle B. H. Long, C. Fairchild, ibid., 1996, 61, 2065.
[43] S. H. Chen, S. Huang, G. Roth, Tetrahedron Lett., 1995, 36, 8933.
[44] I. Ojima, I. Habus, M. Zhao, G. Georg, L. R. Iaysinghe, J. Org. Chem., 1991, 56,1681.
[45] I. Ojima,I. Habus, M. Zhao, M. Zucco, Y. H. Park, C. M. Sun, T. Brigaud, Tetrahed¬ron, 1992, 48, 6985.
[46] R. A. Holton, Eur. Patent. 0400971, 1990
[47] P. H. G. Wiegerinck, L. Fluks, J. B. Hammink, S. J. E. Mulders, F. M. H. Groot, H. L. M. Rozendaal, H. W. Scheeren, J. Org. Chem, 1996, 61, 7092.
[48] I. N. Denis, A. E. Greene, D. Grenard, F. Gueritte-Voegelein, L. Mangatal, P. Potier, J. Am. Chem. Soc., 1988, 110, 5917.
[49] J. N. Denis, A. E. Greene, A. A. Serra, M. J. Luche, J. Org. Chem., 1986, 51, 46.
[50] J. N. Denis, A. Correa, A. E. Greene, ibid., 1990, 55, 1957.
[51] L. Deng, E. N. Jacobsen, ibid., 1992, 57, 4320.
[52] J. N. Denis, A. Correa, A. E. Greene, J . Org. Chem. 1991, 56, 6939.
[53] Z. M. Wang, H. C. Kolb, K. B. Sharpless, ibid., 1994, 59, 5104.
[54] A. M. P. Koskinen, E. K. Karvinen, J. P. Siirlii, J. Chem. Soc. Chem. Comm, 1994, 21.
[55] E. W. Colvin, D. McGarry, M. J. Nugent, Tetrahedron, 1988, 44, 4157.
[56] G. I. Georg, Z. S. Cheruvallath, G. C. B. Harriman, M. Hepperle, H. Park, Bioorg. Med. Chem. Lett., 1993, 3, 2479.
[57] W. A. Rey, R. Droghini, J. Douglas, P. Vemishetti, S. D. Boettger, S. Rache, J. L. Dillon, Can. J. Chem, 1994, 72, 2131.
[58] H. Honig, P. Seufer-Wasserthal, H. Weber, Tetrahedron, 1990, 46, 3841.
[59] R. Brieva, J. Z. Crich, C. J. Sih, J. Org. Chem, 1993, 58, 1068.
[60] R. N. Patel, A. Banerjee, R. Y. Ko, J. M. Howell, W. S. Li, F. T. Comezoglu, R. A. Partyke, L. Szarka, Biotechnol. Appl. Biochem., 1994, 20, 23.
[61] R. N. Patel, A. Banerjee, J. M. Howell, C. G. Namee, D. Brzozowski, D. Mirfakh- rae, V. Nanduri, J. K. Thottrhil, L. Szarka, Tetrahedron Asymmetry, 1993, 4, 2069.
[62] J. Kearns, M. M. Kayser, Tetrahedron Lett., 1994, 35, 2845.
[63] C. S. Swindell, Org. Prep. Proc. Int, 1991, 23, 465.
[64] A. N. Boa, P. R. Jenkins, N. J. Lawrence, Contemporary Organic Synthesis, 1994, vol. 1, 47.
[65] R. A. Holton, R. R. Juo, H. B. Kim, A. D. Williams, S. Harusawa, R. E. Lowenthal, S.Yogai, J. Am. Chem. Soc., 1988, 110, 6558.
[66] K. C. Nikolaou, R. K. Guy, Angew. Chem. Int. Ed. Engl., 1995,34,2079; K. C. Nikolao u, R. K. Guy, W. M. Dai, Angew. Chem, Int. Ed. Engl,. 1994, 33, 15.
[67] R. A. Holton, H. B. Kim, C. Somoza, F. Liang, R. J. Biediger, P. D. Boatman, M. Shindo, C. C. Shmith, S. Kim, H. Nadizadeh, Y. Suzuki, Ch. Tao, P. Y u, S. Tang, J. H. Li, ibid, 1994, 116, 1597.
[68] J. J. Masters, J. T. Link, L. B. Snyder, W. B. Yung, S. J. Danishefsky, Angew. Chem., Int. Ed. Engl., 1995, 34, 1723; S. J. Danishefsky, J. J. Masters, W. B. Young, J. T. Link, L. B. Snyder, T. V. Magee, D. K. Sung, R. C. A. Isaacs, W. G. Bornmann, C. A. Alaimo, C. A. Coburn, M. J. Grandi, J. Am. Chem. Soc., 1996, 118, 2843.
[69] P. A. Wender, N. F. Badham, S. P. Conway, P. E. Floreancig, T. E. Glass, Ch. Granicher, J. B. Houze, J. Janichen, D. Lee, D. G. Marquess, P. L. McGrane, W. Meng, T. P. Mucciaro, M. Muhlebach, M. G. Natchus, H. Plausen, D. B. Rawlins, J. Satkofsky, A. J. Shuker, J. C. Sutton, R. E. Taylor, K. Tamooka, ibid., 1997, 119, 2755.
[70] 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, ibid., 1997, 119, 2757.
[71] C. S. Swindel, N. E. Kraus, S. B. Horwitz, I. Ringel, J. Med. Chem, 1991, 34, 1176.
[72] F. Gueritte-Voegelein, D. Guenard, F. Lavelle, M.-T. LeGoff, L. Mentagal P. Potier, J. Med. Chem., 1991, 34, 992.
[73] L. Mengatel, M. T. Adeline, D. Guenard, F. Gueritte-Voegelein, P. Potier, 7 rahedron, 1989, 45, 4177.
[74] I. Ringel, S. B. Horwitz, J. Natl. Cancer. 1991, 83, 288.
[75] I. Ojima, J. C. Slater, P. Pera, J. M. Veith, A. Abouabdellah, J.-P. Begue, R. J. Bernacki, Bioorg. Med. Chem. Lett., 1997, 2, 133.
[76] I. Ojima, Y. H. Park, I. Fenoglio, O. Duklos, C.-M. Sun, S. D. Kuduk, M. Zucco, G. Appendino, P. Pera, J. M. Veith, R. J. Bernacki, M.-C. Bissery, C. Combeau, P. Virgnaud, J. F. Riou, F. Lavelle, Taxanes Anticancer Agents: Basic Science and Current Status.
[77] G. I. Georg, T. T. Chen, I. Ojima, D. M. Vyas, ACS Symp. Series, Washington, D. C., 1995, 262.
[78] I. Ojima, M. Zucco, O. Duklos, M.-C. Bissery, C. Combeau, P. Virgnad, J. F. Riou, F. Lavelle, J. Med. Chem., 1994, 37, 2603.
[79] A. G. Chaudhary, J. M. Rimoldi, D. G. I. Kingston, J. Org. Chem., 1993, 58, 3798.
[80] J. Kant, S. Huang, H. Wong, C. Fairchild, D. Vyas, V. Farina, Bioorg. Med. Chem. Lett., 1993, 3, 2471.
[81] F. M. Rossi, E. T. Powers, R. Yoon, L. Rosengers, J. Meinwald, Tetrahedron, 1996, 52, 10279.
[82] S. H. Chen, C. Fairchild, S. W. Mamber, V. Farina, J. Org. Chem. 1993, 58, 2927.
[83] J. Kant, W. S. O'Keeffe, S. H. Chen, V. Farina, C. Fairchild, K. Johnston, J. F. Kadow, B. H. Lond, D. Vyas, Tetrahedron Lett., 1994, 35, 5543.
[84] A. G. Chaudhary, J. M. Rimoldi, D. G. I. Kingston, J. Org. Chem., 1993, 58, 3798.
[85] X. Liang, D. G. I. Kingston, C. M. Lin, E. Hamel, Tetrahedron Lett., 1995, 36, 2901.
[86] S. H. Chen, S. Huang, J. Kant, C. Fairchild, J. Wei, V. Farina, J. Org. Chem., 1993,58, 5028.
[87] S. H. Chen, J. M. Wei, V. Farina, Tetrahedron Lett., 1993, 34, 3205.
[88] A. G. Chaudhary, M. M. Gharpure, J. M. Rimoldi, M. D. Chordia, A. L. L. Gunati- laka, D. G. I. Kingston, S. Grover, C. M. Lin, E. Hamel, J. Am. Chem. Soc., 1994, 116, 4097.
[89] K. C. Nicolaou, J. Renaud, P. G. Nantermet, E. A. Couladouros, R. K. Guy, W. Wrasidlo, ibid., 1995, 117, 2049.
[90] K. A. Neidigh, M. M. Gharpure, J. M. Rimoldi, D. G. I. Kingston, Y. Q. Jiang, E. Hamel, Tetrahedron Lett., 1994, 35, 6839.
[91] S. H. Chen, J. F. Kadow, V. Farina, C. R. Fairchild, C. Jonhston, J. Org. Chem., 1994, 59, 6156.
[92] L. L. Klein, C. J. Maring, L. Li, C. M. Yeung, S. A. Thomas, D. J. Grampovnik, J. Plattner, R. F. Henny, ibid., 1994, 59, 2370.
[93] I. Ojima, I. Fenoglio, Y. H. Park, C. M. Sun, G. Appendino, P. Pera, R. J. Bernacki, ibid., 1994, 59, 515.
[94] K. C. Nicolaou, C. F. Clairborne, P. G. Nantermet, E. A. Couladouros, E. J. Sorensen, J. Am. Chem. Soc., 1994,116, 1591; K. C. Nicolaou, C. F. Clairborne, K. Paulvannan, M. H. D. Postema, R. K. Guy, Chem. Eur. J., 1997, 3, 399.
[95] W. B. Yo ung, J. J. Masters, S. J. Danishefsky, J. Am. Chem. Soc., 1995, 117, 5228.
[96] G. Appendino, B. Danieli, J. Jakupovic, E. Belloro, G. Scambia, E. Bombardelli, Tetrahedron Lett., 1997, 38, 4273.
[97] B. Samaranyaka, N. F. Magri, C. Jitrangsri, D. G. I. Kingston, J. Org. Chem., 1991, 56, 5114.

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Bibliografia

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