Design, Synthesis, and Bioactivities of Steroid-Linked Taxol Analogues as Potential Targeted Drugs for Prostate and Breast Cancer

Journal of Natural Products

Volumn 67, Issue 2, 2004, Pages 152-159

  Liu, Changhui ^a   Strobl, Jeannine S ^b   Bane, Susan ^c   Schilling, Jennifer K ^a   McCracken, Meredith ^b   Chatterjee, Sabarni K ^c   Rahim Bata, Rayhana ^b   Kingston, David G I ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^b WEST VIRGINIA UNIVERSITY   (United States)

^c BINGHAMTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2' [4 [3,17BETA DIHYDROXYESTRA 1,3,5(10) TRIENE 16ALPHA YL]BUT 2 ENOYL]TAXOL; 7 [4 [3,17BETA DIHYDROXYESTRA 1,3,5(10) TRIENE 16ALPHA YL]BUT 2 ENOYL]TAXOL; AMMONIUM DERIVATIVE; ESTRADIOL; ESTROGEN RECEPTOR; PACLITAXEL DERIVATIVE; SUCCINIC ACID 3,17BETA DIHYDROXYESTRA 1,3,5(10) TRIENE 11ALPHA YL ESTER 10 DEACETYL 7 EPITAXOL ESTER; SUCCINIC ACID 3,17BETA DIHYDROXYESTRA 1,3,5(10) TRIENE 11ALPHA YL ESTER 2' (3 CARBOXYPROPANOYL) 7 TAXOL ESTER; SUCCINIC ACID 3,17BETA DIHYDROXYESTRA 1,3,5(10) TRIENE 11ALPHA YL ESTER 7 TAXOL ESTER; SUCCINIC ACID 3,17BETA DIHYDROXYESTRA 1,3,5(10) TRIENE 11BETA YL ESTER 2' TAXOL ESTER; UNCLASSIFIED DRUG;

ARTICLE; BREAST CANCER; CANCER CELL; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG DESIGN; DRUG SYNTHESIS; DRUG TARGETING; HUMAN; HUMAN CELL; OVARY CANCER; PROSTATE CANCER;

BREAST NEOPLASMS; DRUG SCREENING ASSAYS, ANTITUMOR; ESTRADIOL; FEMALE; HUMANS; MALE; MOLECULAR STRUCTURE; PACLITAXEL; PROSTATE; STEREOISOMERISM; SUCCINIC ACIDS; TUMOR CELLS, CULTURED;

MINK CELL FOCUS-FORMING VIRUS;

EID: 1442285546     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np030296x     Document Type: Article

References (48)

1. The name taxol was assigned to the chemical compound 1 by Drs. Wall and Wani in 1971, and this name remained in general use until 1991. The name Taxol was then trademarked by Bristol-Myers Squibb for their formulation of the chemical compound taxol on the basis of an existing French trademark for a laxative compound with this name. Since this paper has been submitted in honor of Drs. Wall and Wani, the original name that they assigned for compound 1 is used, rather than the alternative name of paclitaxel. No infringement of the Bristol-Myers Squibb trademark is implied by this usage.
2. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327.
3. (a) Suffness, M.; Wall, M. E. In Taxol: Science and Applications; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995; pp 3-25.
4. (b) Kingston, D. G. I. Chem. Commun. 2001, 867-880.
5. Schiff, P. B.; Fant, J.; Horwitz, S. B. Nature 1979, 277, 665-667.
6. (a) Holmes, F. A.; Walters, R. S.; Theriault, R. L.; Forman, A. D.; Newton, L. K.; Raber, M. N.; Buzdar, A. U.; Frye, D. K.; Hortobagyi, G. N. J. Natl. Cancer Inst. 1991, 83, 1797-1805.
7. (b) Markman, M. Yale Biol. Med. 1991, 64, 583-590.
8. (c) Swain, S. M.; Honig, S. F.; Tefft, M. C.; Walton, L. Invest. New Drugs 1995, 13, 217-222.
9. Levin, M. Drugs Today 2001, 37, 57-65.
10. (a) Kingston, D. G. I.; Jagtap, P. G.; Yuan, H.; Samala, L. In Progress in the Chemistry of Organic Natural Products; Herz, W.; Falk, H.; Kirby, G. W.; Eds.; Springer: Wien, 2002; Vol. 84, pp 53-225.
11. (b) Gueritte, F. Curr. Pharm. Des. 2001, 7, 1229-1249.
12. (c) Miller, M. L.; Ojima, I. Chem. Record 2001, 1, 195-211.
13. (a) Donehower, R. C.; Rowinsky, E. K.; Grochow, L. B.; Longnecker, S. M. ; Ettinger, D. S.; Cancer Treat. Rep. 1987, 71, 1171-1177.
14. (b) Rowinsky, E. K.; Burke, P. J.; Karp, J. E.; Tucker, R. W.; Ettinger, D. S.; Donehower, R. C. Cancer Res. 1989, 49, 4640-4647.
15. (c) Grem, J. L.; Tutsch, K. D.; Simon, K. J.; Alberti, D. B.; Willson, J. K.; Tormey, D. C.; Swaminathan, S.; Trump, D. L. Cancer Treat. Rep. 1987, 71, 1179-1264.
16. (a) Schibler, M. J.; Cabral, F. J. Cell. Biol. 1986, 102, 1522-1531.
17. (b) Kyu-Ho, H. E.; Gehrke, L.; Tahir, S. K.; Credo, R. B.; Cherian, S. P.; Sham, H.; Rosenberg, S. H.; Ng, S. C. Eur. J. Cancer 2000, 36, 1565-1571.
18. (a) Safavy, A.; Raisch, K. P.; Khazaeli, M. B.; Buchsbaum, D. J.; Bonner, J. A. J. Med. Chem. 1999, 42, 4919-4924.
19. (b) Huang, C. M.; Wu, Y. T.; Chen, S. T.; Chem. Biol. 2000, 7, 453-461.
20. (c) Luo, Y.; Prestwich, G. D. Bioconjug. Chem. 1999, 10, 755-763.
21. (d) Lee, J. W.; Lu, J. Y.; Low, P. S.; Fuchs, P. L. Bioorg. Med. Chem. 2002, 10, 2397-2414.
22. (e) Ojima, I.; Geng, X.; Wu, X.; Qu, C.; Borella, C. P.; Xie, H.; Wilhelm, S. D.; Leece, B. A.; Bartle, L. M.; Goldmacher, V. S.; Chari, R. V. J. Med. Chem. 2002, 45, 5620-5623.
23. (a) Beatson, G. T. Lancet 1896, 2, 105-107.
24. (b) Beatson, G. T. Lancet 1896, 2, 162-165.
25. Jensen, E. V.; Suzuki T.; Kawashima, T.; Stumpf, W. E.; Jungblut, P. W.; DeSombre, E. R. Proc. Natl. Acad. Sci. U.S.A. 1968, 59, 632-638.
26. (a) McGuire, W. L.; Chamness, G. C.; Costlow, M. E.; Shepherd, R. E.; Metabolism 1974, 23, 75-100.
27. (b) Fisher, B.; Powles, T. J.; Pritchard, K. J. Eur. J. Cancer 2000, 36, 142-150.
28. (c) Wiseman, L. R.; Goa K. L. Drugs 1997, 54, 141-160.
29. (d) Eppenberger, U.; Wosikowski, K.; Kung, W. Am. J. Clin. Oncol. 1991, 14 (Suppl. 2), 5-14.
30. (a) Ishiki, N.; Onishi, H.; Machida, Y. Biol. Pharm. Bull. 1997, 20, 1096-1102.
31. (b) Gnewuch, C. T.; Sosnovsky, G. Chem. Rev. 1997, 97, 829-1013.
32. (c) James, D. A.; Swamy, N.; Paz, N.; Hanson, R. N.; Ray, R. Bioorg. Med. Chem. Lett. 1999, 9, 2379-2384.
33. (d) Swamy, N.; James, D. A.; Mohr, S. C.; Hanson, R. N.; Ray, R. Bioorg. Med. Chem. 2002, 10, 3237-3243.
34. (e) Kuduk, S. D.; Zheng, F. F.; Sepp-Lorenzino, L.; Rosen, R.; Danishefsky, S. J. Bioorg. Med. Chem. Lett. 1999, 9, 1233-1238.
35. (f) Kuduk, S. D.; Harris, C. R.; Zheng, F. F.; Sepp-Lorenzino, L.; Ouerfelli, Q.; Rosen, N.; Danishefsky, S. J. Bioorg. Med. Chem. Lett. 2000, 10, 1303-1306.
36. http://www.nabco.org
37. Kingston, D. G. I. J. Nat. Prod. 2000, 63, 726-734.
38. Denis, J. N.; Greene, A. E.; Serra, A. A.; Luche, M. J. J. Org. Chem. 1986, 51, 46-50.
39. Tedesco, R.; Fiaschi, R.; Napolitano, E. J. Org. Chem. 1995, 60, 5316-5318.
40. (a) Deutsch, H. M.; Glinski, J. A.; Hernandez, M.; Haugwitz, R. D.; Narayanan, V. L.; Suffness, M.; Zalkow, L. H. J. Med. Chem. 1989, 32, 788-792.
41. (b) Chaudhary, A. G.; Kingston, D. G. I. Tetrahedron Lett. 1993, 34, 4921-4924.
42. Taxol derivative 19 was prepared by protecting the known 2′-(tertbutyldimethylsilyl)-10-deacetyltaxol as its triethylsilyl ether at the C-7 position: Datta, A.; Hepperle, M.; Georg G. I. J. Org. Chem. 1995, 60, 761-763.
43. Chaudhary, A. G.; Rimoldi, J. M.; Kingston, D. G. I. J. Org. Chem. 1993, 58, 3798-3799.
44. Mellado, W.; Magri, N. F.; Kingston, D. G. I.; Garcia-Arenas, R.; Orr, G. A.; Horwitz, S. B. Biochem. Biophys. Res. Commun. 1984, 124, 329-335.
45. (a) Linja M. J.; Savinainen, K. J.; Rammela, T. L.; Isola, J. J.; Visakorpi, T. Prostate 2003, 55, 180-186.
46. (b) Torlakovic, E.; Lilleby, W.; Torlakovic, G.; Fosssa, S. D.; Chibbar, R. Hum. Pathol. 2002, 33, 646-651.
47. (c) Ito, T.; Tachibana, M.; Yamamoto, S.; Hakashima, J.; Murai, M. Eur. Urol. 2001, 40, 557-563.
48. (d) Kau, K. M.; LaSpina, M.; Long, J.; Ho, S. M. Cancer Res. 2000, 60, 3175-3182.