medigraphic.com
Órgano Oficial del Instituto de Ciencias de la Salud, Hospital Escuela y Facultad de Medicina-Xalapa

2016, Número 1

<< Anterior

Rev Med UV 2016; 16 (1)


Generalidades del fármaco Taxol: una revisión sistemática

Barrales-Cureño HJ, Farrera RA, Reyes RC, Hernández FIY, García AE, Chávez SS

Idioma: Español
Referencias bibliográficas: 71
Paginas: 75-91
Archivo PDF: 507.35 Kb.


RESUMEN

La biosíntesis del taxol tiene lugar en la familia Taxaceae, una familia de coníferas del orden Cupressales, que incluye especies de Taxus de todo el mundo. La biomasa de las especies de Taxus contiene diferentes compuestos tales como los isoprenoides, flavonoides, fenilpropanoides y derivados del fenol. El taxol y compuestos análogos se utilizan para tratar el cáncer de seno, cabeza, cuello, pulmón y ovarios. Actualmente las ventas anuales de este medicamento, comercializado con el nombre de Taxol por Bristol-Myers Squibb, se calculan en 1,600 millones de dólares. Uno de los problemas más difíciles para la producción del taxol se debe a las bajas concentraciones que se encuentran en las subespecies de Taxus. Estos problemas pueden ser resueltos mediante cuatro métodos alternativos para obtener el taxol sin afectar a los bosques: síntesis total, semisíntesis a partir de su precursor natural, producción de taxol por hongos o bacterias y cultivo in vitro de callos, células vegetales u órganos tales como el tallo, estróbilos y raíces, ya sea por sistemas de inmersión temporal o mediante el uso de biorreactores. Los principales objetivos de este artículo de revisión científica son: conceptualizar el significado de los taxoides y su importancia en el área de la oncología humana; definir el mecanismo de acción biológico-específico del taxol; las ventajas y desventajas de los métodos biotecnológicos alternativos utilizados en la producción del taxol tales como: la síntesis química total, la semisíntesis orgánica y mediante el cultivo in vitro de protoplastos; así como la producción de la enzima taxadieno sintasa mediante ingeniería genética en microorganismos; finalmente se menciona la biosíntesis del taxol junto con sus compuestos análogos.


REFERENCIAS (EN ESTE ARTÍCULO)

  1. Altstadt, T. J, Fairchild, C. R, Golik, J, Johnston, K. A, Kadow, J. F, Lee, F. Y, Long B. H, Rose W. C, Vyas D. M, Wong Z. H, Wu M. L, Wittman M. D, (2001). Synthesis and antitumor activity of novel C-7 paclitaxel ethers: discovery of BMS-184476, Journal of Medicinal Chemistry, 44, 4577-4583.

  2. Aoyagi, H, DiCosmo F, Tanaka H, (2002). Efficient paclitaxel production using protoplasts isolated from cultured cells of Taxus cuspidata. Planta Medica, 68(5), 420-424.

  3. Arsenaulta, A. L, Lhotáka S, Hunter W. L, Banquerigoc M. L. C, Brahn E, (1998). Taxol involution of collagen-induced arthritis: Ultrastructural correlation with the inhibition of synovitis and neovascularization. Clinical Immunology and Immunopathology, 86, 280-289.

  4. Baloglu, E, Kingston D. G, (1999). The taxane diterpenoids. Journal of Natural Products, 62(10), 1448-1472.

  5. Barrales, C. H. J, De la Rosa M. R, Villegas, O. S, (2012). Hacia una genética celular del cáncer. Revista la Ciencia y el Hombre, 25, 1-6.

  6. Barrales, C. H. J, Soto, H. M, (2011). Bioquímica de los taxoides utilizados contra el cáncer. Revista de Educación Bioquímica, 30(1), 12-20.

  7. Barrales, C. H. J, Soto, H. M, Ramos, V. A, Trejo, T. L, Martínez, V. M, Ramírez, G. M, López, U. J, (2011). Extracción y cuantificación de taxoides por HPLC en hojas in situ y en callos inducidos in vitro de Taxus globosa Schlecht. Spanish Journal of Rural Development, 2, 103‒114.

  8. Barrales, C. H. J, Soto, H. M, (2012). Taxoides: metabolitos secundarios del árbol del tejo (Taxusspp.). Revista Chapingo Serie Ciencias Forestales y del Ambiente, 18(2), 207-21.

  9. Ballero, M, Loi, M. C, Van Rozendaal, E. L. M, van Beek, T. A, van de Haar, C, Poli F, Appendino G, (2003). Analysis of pharmaceutically relevant taxoids in wild yew trees from Sardinia. Fitoterapia, 74, 34-39.

  10. Barrales, C. H. J, Reyes, R. C, Chávez, S. S. (2015). Producción in vitro de taxoides anticancerígenos de Taxus spp. Editorial Académica Española. 76 pag.

  11. Barrales, C. H. J, Soto, H. M, Ramos, V. A, Luna, P. G, Trejo, T. L, Martínez, V. M, Ramírez, G. M, (2009). Inducción de callos in vitro de Taxus globosa a partir de acículas. Revista Latinoamericana de Química. Suplemento especial ISNN 0370-5943, pp. 89.

  12. Brown, R. G, Hull, F. E, (1951). Taxus (yew) poisoning of cattle. Journal of the American Veterinary Medical Association, 118, 398-399.

  13. Commercon, A, Bourzat, J. D, Didier, E, Lavelle, F, (1995). Taxane anticancer agents: Basic Science and Current Status (Georg Gl, Chen TT, Ojima I, Vyas DM eds.) American Chemical Society, Washington DC. 233-246.

  14. Chaudhary, A. G, Gharpure, M. M, Rimoldi, J. M, Chordia, M. D, Kingston, D. G. I, Grover S, Lin, C. M, Hamel, E, Gunatilaka, A. A, (1994). Leslie Unexpectedly Facile Hydrolysis of the 2-Benzoate Group of Taxol and Syntheses of Analogs with Increased Activities. Journal of the American Chemical Society, 116(9), 4097-4098.

  15. Chaudhary, A. G, Kingston, D. G. I, (1993). Synthesis of 10-deacetoxytaxol and 10-deoxytaxotere. Tetrahedron Letters, 34(31), 4921-4924.

  16. Chen, S. H, Huang, S, Kant, J, Fairchild, C, Wei, J, Farina, V, (1993). Synthesis of 7-Deoxy- and 7, 10-Dideoxytaxol via Radical Intermediates. Journal of Organic Chemistry, 58, 5028-5029.

  17. Chordia, M. D, Chaudhary, A. G, Kingston, D. G. I, Qing, J. Y, Hamel, E, (1994). Synthesis and biological evaluation of 4-deacetoxypaclitaxel. Tetrahedron Letters, 35(37), 6843-6846.

  18. Croteau, R, Ketchum, R. E. B, Long, R. M, Kaspera, R, Wildung, M. R, (2006). Taxol biosynthesis and molecular genetics. Phytochemistry Reviews, 5, 75-97.

  19. Daniewski, W. M, Gumulka, M, Anczewski, W, Masnyk, M, Bloszyk, E, Gupta, K. K, (1998). Why the yew tree (Taxus baccata) is not attacked by insects. Phytochemistry, 49(5), 1279-1282.

  20. Downing, K. H, Nogales, E, (1999). Crystallographic structure of tubulin: implications for dynamics and drug binding. Cell Structure Function, 24(5), 269-275.

  21. Eisenreich, W, Menhard, B, Hylands, PJ, Zenk, M. H, Bacher, A, (1996). Studies on the biosynthesis of taxol: the taxane carbon skeleton is not of mevalonoid origin. Proceedings of the National Academy of Sciences U S A, 93(13), 6431-6436.

  22. Eisenreich, W, Rohdich, F, Bacher, A, (2001). Deoxyxylulose phosphate pathway to terpenoids. Trends Plant Science, 6(2), 78-84.

  23. Eisenreich, W, Schwarz, M, Cartayrade, A, Arigoni, D, Zenk, M. H, Bacher, A, (1998). The deoxyxylulose phosphate pathway of terpenoid biosynthesis in plants and microorganisms. Chemistry & Biology, 5(9), 221-233.

  24. Fett-Neto, A. G, Dicosmo, F, Reynolds, W. F, Sakata, K, (1992). Cell culture of Taxus as a source of the antineoplastic drug taxol and related taxanes. Biotechnology, 10, 1572-1575.

  25. Floss, H. G, Mocek, U, (1995). Biosynthesis of taxol. Taxol: Science and Application. M, S. Boca Raton, CRC Press: 191-208.

  26. Fu, Y. J, Zu, Y. G, Li, S. M, Sun, R, Efferth, T, Liu, W, Jiang, S. G, Luo, H, Wang, Y, (2008). Separation of 7-xylosyl-10-deacetyl paclitaxel and 10-deacetylbaccatin III from the remainder extracts free of paclitaxel using macroporous resins. Journal of Chromatography, 1177, 77-86.

  27. Gueritte-Voegelein, F, Guenard, D, Potier, P, (1987). Taxol and derivatives: a biogenetic hypothesis. Journal of Natural Products, 50(1), 9-18.

  28. Han, K. H, Fleming, P, Walker, K, Laper, M, Chilton, W. S, Mocek, U, Gordon, M. P, Floss, H. G, (1994). Genetic transformation of mature Taxus: An approach to genetically control the in vitro production of the anticancer drug, taxol. Plant Science, 95, 187-196.

  29. Hezari, M, Lewis, N. G, Croteau, R, (1995). Purification and characterization of taxa-4(5),11(12)-diene synthase from pacific yew (Taxus brevifolia) that catalyzes the first committed step of taxol biosynthesis. Archives of Biochemistry and Biophysics, 322(2), 437-444.

  30. Holton, R. A, Somoza, C, Kim, H. B, Liang, F, Biediger, R. J, Boatman, D, Shindo, M, Smith, C. C, Kim, S, Nadizadeh, H, Suzuki, Y, Tao, C, Vu, P, Tang, S, Zhang, P, Murthi, K. K, Gentile, L. S, Liu, J. H, (1994). First total synthesis of taxol. I. Functionalization of the B ring. Journal of the American Chemical Society, 116, 1597-1598.

  31. Huang, K. X, Huang, Q. L, Wildung, M. R, Croteau, R, Scott, A. I, (1998). Overproduction in Escherichia coli, of soluble taxadiene synthase, a key enzyme in the taxol biosynthetic pathway. Protein expression and purification, 13, 90-96.

  32. Huang, Q, Roessner, C. A, Croteau, R, Scott A. I, (2001). Engineering Escherichia coli for the synthesis of taxadiene, a key intermediate in the biosynthesis of taxol. Bioorganic & Medicinal Chemistry, 9, 2237-2242.

  33. Itokawa, H, (2003). Introduction. Taxus. The Genus Taxus. H. Itokawa, K.-H. L. London, New York Taylor and Francis: 1-18.

  34. Ketchum, R. E. B, Rithner, C. D, Qiu, D, Kim, Y. S, Williams, R. M, Croteau, R. B, (2003). Taxus metabolomics: methyl jasmonate preferentially induces production of taxoids oxygenated at C-13 in Taxus x media cell cultures. Phytochemistry, 62(6), 901-909.

  35. Kewal, K. J. Applications of Biotechnology in Oncology (2013) SpringerLink: Bücher Springer Science & Business Media, 855 pp.

  36. Kingston, D. G, Bane, S, Snyder, J. P, (2005). The taxol pharmacophore and the T-taxol bridging principle. Cell Cycle, 4(2), 279-289.

  37. Kingston, D. G. I, (2001). Taxol, a molecule for all seasons. Chemical Communications, 10, 867-880.

  38. Kingston, D. G, Newman, D. J, (2007). Taxoids: cancer-fighting compounds from nature. Current opinion in drug discovery & development Journal, 10(2), 130-144.

  39. Kobayashi, J, Shigemos, H, (2004). Biological activity and chemistry of taxoids from the japanese yew, Taxus cuspidata. Journal of Natural Products, 67(2), 245-256.

  40. Koepp, A. E, Hezari, M, Zajicek, J, Vogel, B. S, Lafever, R. E, Lewis, N. G, Croteau, R, (1995). Cyclization of geranylgeranyl diphosphate to taxa-4(5),11(12)-diene is the committed step of taxol biosynthesis in pacific yew. Journal of Biological Chemistry, 270(15), 8686-8690.

  41. Kolewe, M. E, Gaurav, V, Roberts, S. C, (2008). Pharmaceutically active natural product synthesis and supply via plant cell culture technology. Molecular Pharmacology, 5(2), 243-256.

  42. Kuzuyama, T, Seto, H, (2003). Diversity of the biosynthesis of the isoprene units. Natural Product Reports, 20(2), 171-183.

  43. Li, S. M, Fu, Y. J, Zu, Y. G, Sun, R, Wang, Y, Zhang, L, Luo, H, Gu, C. B, Efferth, T, (2009). Determination of paclitaxel and other six taxoids in Taxus species by high-performance liquid chromatography-tandem mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis, 49, 81-89.

  44. Lowe, J, Li, H, Downing, K. H, Nogales, E, (2001). Refined structure of alpha beta-tubulin at 3.5 A resolution. Journal of Molecular Biology, 313(5), 1045-1057.

  45. Luo, J. P, Mu, Q, Gu, Y. H, (1999). Protoplast culture and paclitaxel production by Taxus yunnensis. Plant Cell, Tissue and Organ Culture, 59, 25-29.

  46. Masters, J. J, Link, J. T, Snyder, L. B, Young, W. B, Danishefsky, S. J, (1995). A total synthesis of taxol. Angewandte Chemie International Edition; 34(16), 1723-1726.

  47. Morihira, K, Hara, R, Kawahara, S, Nishimori, T, Nakamura, N, Kusama, H, Kuwajima, I. J, (1998). Enantioselective total synthesis of taxol. Journal of the American Chemical Society, 120, 12980-12981.

  48. Mukaiyama, T, Shiina, I, Iwadare, H, Saitoh, M, Nishimura, T, Ohkawa, N, Sakoh, H, Nishimura, K, Tani, Y. I, Hasegawa, M, Yamada, K, Saitoh, K. Chem, (1999). Asymmetric total synthesis of Taxol (R). European Journal, 5, 121- 161.

  49. Mustafa, K, Yinghua, J, Robert, M. C, Rodney, C, David, W. C, (2011). Taxadiene synthase structure and evolution of modular architecture in terpene biosynthesis. Nature, 469, 116-122.

  50. Neidigh, K. A, Gharpure, M. M, Rimoldi, J. M, Kingston, D. G. I, Qing, J. Y, Hamel, E, (1994). Synthesis and biological evaluation of 4-deacetylpaclitaxel. Tetrahedron Letters, 35(37), 6839-6842.

  51. Nicolaou, K. C, Zang, Z, Liu, J. J, Ueno, H, Nantermet, P. G, Guy, R. K, Claiborne, C. F, Renaud, J, Couladouros, E. A, Paulvannan, K, Sorensen, E. J, (1994). Total synthesis of taxol. Nature, 367, 630-634.

  52. Ogden, L, (1988). Taxus (Yews) a Highly Toxic Plant. Veterinary and Human Toxicology, 30(6), 563-564.

  53. Ojima, I, Chakravarty, S, Inoue, T, Lin, S, He, L, Horwitz, S. B, Kuduk, S. D, Danishefsky, S. J, (1999). A common pharmacophore for cytotoxic natural products that stabilize microtubules. Proceedings of the National Academy of Sciences U. S. A, 96, 4256-4261.

  54. Patel, R. N, (1998). Tour of paclitaxel. Annual Review of Microbiology, 98, 361-395.

  55. Rohmer, M, (1999). The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants. Natural Product Reports, 16(5), 565-574.

  56. Schrijvers, D, Vermorken, J. B, (2000). Role of taxoids in head and neck cancer. The Oncologist, 5, 199-208.

  57. Schuler, M. A. Plant cytochrome P450 monooxygenases, 1996). Critical Reviews in Plant Sciences, 15(3), 235- 284.

  58. Stierle, A, Strobel, G, Stierle, D, (1993). Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of Pacific yew. Science, 260, 214-216.

  59. Trapp, S. C, Croteau, R. B, (2001). Genomic organization of plant terpene synthases and molecular evolutionary implications. Genetics, 158(2), 811-832.

  60. Walker, K, Fujisaki, S, Long, R, Croteau, R, (2002). Molecular cloning and heterologous expression of the C-13 phenylpropanoid side chain-CoA acyltransferase that functions in taxol biosynthesis. Proceedings of the National Academy of Sciences of the United States of America, 99(20), 12715-12720.

  61. Wani, M. C, Taylor, H. L, Wall, M. E, Coggon, P, Mcphail, A. T, (1971). Plant antitumor agents. Isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia Journal of the American Chemical Society, 93, 2325-2326.

  62. Wender, P. A, Badham, N. F, Conway, S. P, Floreancig, P. E, Glass, T. E, Granicher, C, Houze, J. B, Janichen, J, Lee, D, Marquess, D. G, McGrane, P. L, Meng, W, Mucciaro, T. P, Muhlebach, M, Natchus, M. G, Paulsen, H, Rawlins, D. B, Satkofsky, J, Shuker, A. J, Sutton, J. C, Taylor, R. E, Tomooka, K, (1997). The pinene path to taxanes: 5. Stereocontrolled synthesis of a versatile taxane precursor. Journal of the American Chemical Society, 119, 2755-2756.

  63. Wildung, M. R, Croteau, R, (1996). A cDNA clone for taxadiene synthase, the diterpene cyclase that catalyzes the committed step of taxol biosynthesis. Journal of Biological Chemistry, 271(16), 9201-9204.

  64. Woo, D. D. L, Miao, S. Y. P, Pelayo, J. C. Woolf, A. S, (1994). Taxol inhibits progression of congenital polycystic kidney disease. Nature, 368, 750-753.

  65. Hui Xiao, Pascal Verdier-Pinard, Narcis Fernández-Fuetes, Berta Burd, Ruth Angeletti, Andras Fiser, Susan Band Horwitz and George A. Orr. 2006. Insights into the mechanism of microtubule stabilization by Taxol. Proceedings of the National Academy of Sciences of the United States of America. Vol. 103. No. 27. 10166-10173.

  66. Xiong, Z. Q, Yang, Y. Y, Zhao, N, Wang, Y, (2013). Diversity of endophytic fungi and screening of fungal paclitaxel producer from Anglojap yew, Taxus x media. Microbiology, 13:71-80.

  67. oung, D. H, Michelotti, EL, Swindell, C. S, Krauss, N. E, (1992). Antifungal Properties of Taxol and Various Analogs. Experientia, 48(9), 882-885.

  68. Yukimune, Y, Tabata, H, Higashi, Y, Hara, Y, (1996). Methyl jasmonate induced overproduction of paclitaxel and baccatin III in Taxus cell suspension cultures. Nature Biotechnology, 14, 1129-1132.

  69. Zhong, J. (2002). Plant cell culture for production of paclitaxel and other taxanes. Bioscience Bioengineering, 94(6), 591-599.

  70. Zhou, D, Zhao, K, Ping, W, Ge, J, Ma, X, Jun, L, (2005). Study on the mutagénesis of protoplasts from paclitaxel-producing fungus Nodulisporium sylviforme. The Journal of American Science, 1(1), 55-62.

  71. Zu, Y. G, Fu, Y. J, Li, S. M, Sun, R, Li, Q. Y, Schwarz, G, (2006). Rapid separation of four main taxoids in Taxus species by combined LLP-SPE-HPLC (PDA) procedure. Journal of Separation Science, 29, 1237-44.




2020     |     www.medigraphic.com