Recent Progress in the Chemistry and Biology of Paclitaxel (TaxolTM) and Related Taxanes

Plant Bioactives and Drug Discovery: Principles, Practice, and Perspectives

Volumn , Issue , 2012, Pages 263-336

  Qi, Jun ^a   Zhao, Jielu ^a   Kingston, David G I ^a  

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

Author keywords

Binding mode, conformation of paclitaxel on tubulin; Microtubule interactive mitotic inhibitors, in cancer chemotherapy; New chemistry of paclitaxel; Paclitaxel (TaxolTM) chemistry, biology, and related taxanes; Potent new analogs of paclitaxel and drug targeting

Indexed keywords

EID: 84886113184     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118260005.ch8     Document Type: Chapter

References (250)

1. Fu, Y., Li, S., Zu, Y., Yang, G., Yang, Z., Luo, M., Jiang, S.,Wink, M., Efferth, T. (2009). Medicinal chemistry of paclitaxel and its analogues. Current Medicinal Chemistry, 16, 3966-3985.
2. Ojima, I., Das, M. (2009). Recent advances in the chemistry and biology of new generation taxoids. Journal of Natural Products, 72, 554-565.
3. Saloustros, E., Mavroudis, D., Georgoulias, V. (2008). Paclitaxel and docetaxel in the treatment of breast cancer. Expert Opinion on Pharmacotherapy, 9, 2603-2616.
4. Ferlini, C., Gallo, D., Scambia, G. (2008). New taxanes in development. Expert Opinion on Investigational Drugs, 17, 335-347.
5. Hudis, C., Dang, C. (2008). The taxane limbo: How long can we go? Journal of the National Cancer Institute, 100, 761-763.
6. Kingston, D.G.I. (2001). Taxol, a molecule for all seasons. Chemical Communications, 867-880.
7. Kingston, D.G.I. (2011). Taxol and Tbs analogs In: Anticancer Agents from Natural Products Ed. by Gragg, G.C., Kingston, D.G.I., Newman, D.J. CRC Press, Boca Raton, FL pp. 123-175.
8. Wall, M.E.,Wani, M.C., Recent progress in plant anti-tumor agents. In: 153rd National Meeting of the American Chemical Society, Miami Beach, FL, Abstr. M006, 1967.
9. Wani, M.C., Taylor, H.L., Wall, M.E., Coggon, P., McPhail, A.T. (1971). Plant antitumor agents: VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. Journal of the American Chemical Socisty, 93, 2325-2327.
10. Suffness, M.,Wall, M.E., Discovery and development of taxol. In: Suffness, M., editor. Taxol: Science and Applications, CRC Press, Boca Raton, FL, 1995, pp. 3-25.
11. Schiff, P.B., Fant, J., Horwitz, S.B. (1979). Promotion of microtubule assembly in vitro by taxol. Nature, 277, 665-667.
12. McGuire, W.P., Rowinsky, E.K., Rosenshein, N.B., Grumbine, F.C., Ettinger, D.S., Armstrong, D.K., Donehower, R.C. (1989). Taxol: A unique antineoplastic agent with significant activity in advanced ovarian epithelial neoplasms. Annals of Internal Medicine, 111, 273-279.
13. 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. (1991). Phase II trial of taxol, an active drug in the treatment of metastatic breast cancer. Journal of the National Cancer Institute, 83, 1797-1805.
14. Gueritte-Voegelein, F., Senilh, V., David, B., Guenard, D., Potier, P. (1986). Chemical studies of 10-deacetyl baccatin: III. Hemisynthesis of taxol derivatives. Tetrahedron, 42, 4451-4460.
15. Denis, J.-N., Greene, A.E., Guenard, D., Gueritte-Voegelein, F., Mangatal, L., Potier, P. (1988). A highly efficient, practical approach to natural taxol. Journal of the American Chemical Society, 110, 5917-5919.
16. Clarke, S.J., Rivory, L.P. (1999). Clinical pharmacokinetics of docetaxel. Clinical Pharmacokinetics, 36, 99-114.
17. Kant, J., O'Keeffe,W.S., Chen, S.-H., Farina,V., Fairchild, C., Johnston, K., Kadow, J.F., Long, B.H., Vyas, D. (1994). A chemoselective approach to functionalize the C-10 position of 10-deacetylbaccatin: III. Synthesis and biological properties of novel C-10 taxol analogues. Tetrahedron Letters, 35, 5543-5546.
18. Denduluri, N., Swain, S.M. (2008). Ixabepilone for the treatment of solid tumors: A review of clinical data. Expert Opinion on Investigational Drugs, 17, 423-435.
19. Baloglu, E., Kingston, D.G.I. (1999). The taxane diterpenoids. Journal of Natural Products, 62, 1448-1472.
20. Shi, Q.-W., Kiyota, H. (2005). Newnatural taxane diterpenoids from Taxus species since 1999. Chemistry and Biodiversity, 2, 1597-1623.
21. Shen, Y.-C., Chen, C.-Y., Hung, M.-C. (2000). Taxane diterpenoids from seeds of Taxus mairei. Chemical and Pharmaceutical Bulletin, 48, 1344-1346.
22. Shen, Y.-C., Prakash, C.V.S., Chen, Y.-J., Hwang, J.-F., Kuo, Y.-H., Chen, C.-Y. (2001). Taxane diterpenoids from the stem bark of Taxus mairei. Journal of Natural Products, 64, 950-952.
23. Shen, Y.,Wang, S., Pan, Y., Lo, K., Chakraborty, R., Chien, C., Kuo, Y., Lin, Y. (2002). New taxane diterpenoids from the leaves and twigs of Taxus sumatrana. Journal of Natural Products, 65, 1848-1852.
24. Galm, U., Hager, M.H., Van Lanen, S.G., Ju, J., Thorson, J.S., Shen, B. (2005). Antitumor antibiotics: Bleomycin, enediynes, and mitomycin. Chemical Reviews, 105, 739-758.
25. Torregiani, E., Rafaiani, G., Barboni, L., Appendino, G. (1995). A serendipitous clue to the biogenesis of taxchins. Tetrahedron Letters, 36, 7127-7128.
26. Shen, Y.-C., Lin, Y.-S., Cheng, Y.-B., Cheng, K.-C., Khalil, A.T., Kuo, Y.-H., Chien, C.-T., Lin, Y.-C. (2005). Novel taxane diterpenes from Taxus sumatrana with the first C-21 taxane ester. Tetrahedron, 61, 1345-1352.
27. Shen, Y.-C., Lin, Y.-S., Hsu, S.-M., Khalil, A.T.,Wang, S.-S., Chien, C.-T., Kuo, Y.-H., Chou, C.-H. (2007).Tasumatrols P-T, five newtaxoids from Taxus sumatrana. Helvetica Chimica Acta, 90, 1319-1329.
28. Shen,Y.-C.,Wang, S.-S., Chien, C.-T., Kuo,Y.-H., Khalil, A.T. (2008).Tasumatrols U-Z, taxane diterpene esters from Taxus sumatrana. Journal of Natural Products, 71, 576-580.
29. Wang, S.-S., El-Razek, M.H.A., Chen, Y.-C., Chien, C.-T., Guhb, J.-H., Kuod, Y.-H., Shen, Y.-C. (2009). Abeo-taxane diterpenoids from the Taiwanese Yew Taxus sumatrana. Chemistry and Biodiversity, 6, 2255-2262.
30. Luh, L.-J., El-Razek, M.H.A., Liaw, C.-C., Chen, C.-T.A., Lin, Y.-S., Kuo, Y.-H., Chien, C.-T., Shen, Y.-C. (2009). Tri-and bicyclic taxoids from the Taiwanese Yew Taxus sumatrana. Helvetica Chimica Acta, 92, 1349-1358.
31. Kosugi, K., Sakai, J.-I., Zhang, S., Watanabe, Y., Sasaki, H., Suzuki, T., Hagiwara, H., Hirata, N., Hirose, K., Ando, M., Tomida, A., Tsuruo, T. (2000). Neutral taxoids from Taxus cuspidata as modulators of multidrug-resistant tumor cells. Phytochemistry, 54, 839-845.
32. Zhang, J., Sauriol, F., Mamer, O., You, X.-L., Alaoui-Jamali, M.A., Batist, G., Zamir, L.O. (2001). New taxane analogues from the needles of Taxus canadensis. Journal of Natural Products, 64, 450-455.
33. Klein, L.L. (1993). Synthesis of 9-dihydrotaxol: A novel bioactive taxane. Tetrahedron Letters, 34, 2047-2050.
34. Prasain, J.K., Stefanowicz, P., Kiyota, T., Habeichi, F., Konishi, Y. (2001). Taxines from the needles of Taxus wallichiana. Phytochemistry, 58, 1167-1170.
35. Shi, Q.W., Sauriol, F., Lesimple, A., Zamir, L.O. (2004). First three examples of taxanederived di-propellanes in Taxus canadensis needles. Chem. Comm., 544-545.
36. Chattopadhyay, S.K., Pal, A., Maulik, P.R., Kaur, T., Garg, A., Khanuja, S.P.S. (2006). Taxoid from the needles of the Himalayan yew Taxus wallichiana with cytotoxic and immunomodulatory activities. Bioorganic and Medicinal Chemistry Letters, 16, 2446-2449.
37. Barboni, L., Pierluigi, G., Torregiani, E.G.A., Gabetta, B., Zini, G., Bombardelli, E. (1993). Taxanes from the needles of Taxus Wallichiana. Phytochemistry, 33, 145-150.
38. Zhang, M.-L., Dong, M., Li, Z.-N., Li, L.-G., Sauriol, F., Huo, C.-H., Shi, Q.-W., Gu, Y.-C., Kiyota, H., Cong, B. (2008).A new taxane composed of two N-formyl rotamers from Taxus canadensis. Tetrahedron Letters, 49, 3405-3408.
39. Holton, R.A., Somoza, C., Kim, H.-B., Liang, F., Biediger, R.J., Boatman, P.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.N., Liu, J.H. (1994). First total synthesis of taxol: 1. Functionalization of the B ring. Journal of the American Chemical Society, 116, 1597-1598.
40. Holton, R.A., Kim, H.B., Somoza, C., Liang, F., Biediger, R.J., Boatman, P.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.N., Liu, J.H. (1994). First total synthesis of taxol: 2. Completion of the C and D rings. Journal of the American Chemical Society, 116, 1599-1600.
41. Nicolaou, K.C.,Yang, 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.
42. Danishefsky, S.J., Masters, J.J., Young, W.B., Link, J.T., Snyder, L.B., Magee, T.V., Jung, D.K., Isaacs, R.C.A., Bornmann, W.G., Alaimo, C.A., Coburn, C.A., Di Grandi, M.J. (1996). Total synthesis of baccatin III and taxol. Journal of the American Chemical Society, 118, 2843-2859.
43. 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., Tommoka, K. (1997). The pinene path to taxanes: 5. Stereocontrolled synthesis of a versatile taxane precursor. Journal of the American Chemical Society, 119, 2755-2756.
44. Wender, P.A., Badham, N.F., Conway, S.P., Floreancig, P.E., Glass, T.E., Houze, J.B., Krauss, N.E., Lee, D., Marquess, D.G., McGrane, P.L., Meng, W., Natchus, M.G., Shuker, A.J., Sutton, J.C., Taylor, R.E. (1997). The pinene path to taxanes: 6. A concise stereocontrolled synthesis of taxol. Journal of the American Chemical Society. 119, 2757-2758.
45. 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. (1999). Asymmetric total synthesis of taxol. Chemistry -A European Journal, 5, 121-161.
46. Cragg, G.M., Schepartz, S.A., Suffness, M., Grever, M.R. (1993). The taxol supply crisis. New NCI policies for handling the large scale production of novel natural product anticancer and anti-HIV agents. Journal of Natural Products, 56, 1657-1668.
47. Kusama, H., Hara, R., Kawahara, S., Nishimori, T., Kashima, H., Nakamura, N., Morihira, K., Kuwajima, I. (2000). Enantioselective total synthesis of (-)-taxol. Journal of the American Chemical Society, 122, 3811-3820.
48. Paquette, L.A., Lo, H.Y. (2003). Chemical modification of a highly functionalized taxane. The consequences of an absent bridgehead double bond on oxetane D-ring construction. Journal of Organic Chemistry, 68, 2282-2289.
49. Petit, M., Chouraqui, G., Phansavath, P., Aubert, C., Malacria, M. (2002). New efficient construction of the ABC core of the taxoids via a sequence of consecutive cobalt(I)-mediated [2{thorn}2{thorn}2] and [4{thorn}2] cyclizations. Organic Letters, 4, 1027-1029.
50. Chouraqui, G., Petit, M., Phansavath, P., Aubert, C., Malacria, M. (2006). From an acyclic, polyunsaturated precursor to the polycyclic taxane ring system: The [4{thorn}2]/[2{thorn}2{thorn}2] and [2{thorn}2{thorn}2]/[4{thorn}2] cyclization strategies. European Journal of Organic Chemistry, 6, 1413-1421.
51. Laurent, A., Villalva-Servin, N.P., Forgione, P., Wilson, P.D., Smil, D.V., Fallis, A.G. (2004). Part 1: Efficient strategies for the construction of variably substituted bicyclo [5.3.1]undecenones (AB taxane ring systems). Canadian Journal of Chemistry, 82, 215-226.
52. Villalva-Servin, N.P., Laurent, A., Fallis, A.G. (2004). Part 2: Efficient strategies for the construction of variably substituted bicyclo[5.3.1]undecenones (AB-taxane ring systems) and their conversion to tricyclo[9.3.1.0]pentadecenones (ABC taxane ring systems) and bicyclo[2.2.2]octanones. Canadian Journal of Chemistry, 82, 227-239.
53. Hamon, S., Birlirakis, N., Toupet, L., Arseniyadis, S. (2005). Stereoselective construction of a highly functionalized taxoid ABC-ring system: The C2-C9 oxa-bridge approach. European Journal of Organic Chemistry, 2005, 4082-4092.
54. Chavan, S.P., Chavan, S.P., Sonawane, H.R., Kalkote, U.R., Sudrik, S.G., Gonnade, R.G., Bhadbhade, M.M. (2007). Utilization of the versatility of sulfur in C-C bond formation and cleavage: Synthesis of ABC taxoid skeletons. European Journal of Organic Chemistry, 2007, 3277-3280.
55. Enomoto, T., Morimoto, T., Ueno, M., Matsukubo, T., Shimada, Y., Tsutsumi, K., Shirai, R., Kakiuchi, K. (2008). A novel route for the construction of taxol ABC-ring framework: Skeletal rearrangement approach to AB-ring and intramolecular aldol approach to C-ring. Tetrahedron, 64, 4051-4059.
56. Goldring,W.P.D., Pattenden, G., Rimmington, S.L. (2009). Synthesis of a tetraoxy-bisnortaxadiene, en route to taxol, using a cascade radical cyclisation sequence. Tetrahedron, 65, 6670-6681.
57. Kim, S.-K., Kim, H.-K. (2000). Synthesis of new Taxol side chain precursor from Ltartaric ester. Bulletin of the Korean Chemical Society, 21, 1047-1048.
58. Wuts, P.G.M., Gu, R.L., Northuis, J.M. (2000). Synthesis of (2R, 3S)-isobutyl phenylisoserinate, the taxol side chain, from ethyl benzoylacetate. Tetrahedron: Asymmetry, 11, 2117-2123.
59. Hamamoto, H., Mamedov, V.A., Kitamoto, M., Hayashi, N., Tsuboi, S. (2000). Chemoenzymatic synthesis of the C-13 side chain of paclitaxel (Taxol) and docetaxel (Taxotere). Tetrahedron: Asymmetry, 11, 4485-4497.
60. Aggarwal, V.K., Vasse, J.-L. (2003). Asymmetric sulfur ylide mediated aziridination: Application in the synthesis of the side chain of taxol. Organic Letters, 5, 3987-3990.
61. Choudary, B.M., Chowdari, N.S., Madhi, S., Kantam, M.L. (2003). A trifunctional catalyst for one-pot synthesis of chiral diols via heck coupling-N-oxidation-asymmetric dihydroxylation: Application for the synthesis of diltiazem and taxol side chain. Journal of Organic Chemistry, 68, 1736-1746.
62. Castagnolo, D., Armaroli, S., Corelli, F., Botta, M. (2004). Enantioselectiv synthesis of 1-aryl-2-propenylamines: A newapproach to a stereoselective synthesis of the taxol side chain. Tetrahedron, 15, 941-949.
63. Borah, J.C., Gogoi, S., Boruwa, J., Kalita, B., Barua, N.C. (2004). A highly efficient synthesis of the C-13 side-chain of taxol using Shibasaki's asymmetric Henry reaction. Tetrahedron Letters, 45, 3689-3691.
64. Torssell, S., Kienle, M., Somfai, P. (2005). 1,3-Dipolar cycloadditions of carbonyl ylides to aldimines: A three-component approach to syn-a-hydroxy-b-amino esters. Angewandte Chemie International Edition, 44, 3096-3099.
65. Wang, Y., He, Q., Wang, H., Zhou, X., Huang, Z., Qin, Y. (2006). Highly diastereoselective enolate anddition of O-protected a-hydroxyacetate to (SR)-tert-butanesulfinylimines: Synthesis of taxol side chain. Journal of Organic Chemistry, 71, 1588-1591.
66. Dziedzic, P., Vesely, J., Cordova, A. (2008). Catalytic asymmetric synthesis of the docetaxel (Taxotere) side chain: Organocatalytic highy enantioselective synthesis of esterification-ready a-hydroxy-b-amino acids. Tetrahedron Letters, 49, 6631-6634.
67. Munoz-Hernandez, L., Soderquist, J.A. (2009). Asymmetric g-methoxyallylation with the robust 10-TMS-9-borabicyclo[3.3.2]decanes. Organic Letters, 11, 2571-2574.
68. Qian, Y., Xu, X., Jiang, L., Prajapati, D., Hu, W. (2010). A strategy to synthesize taxol side chain and (-)-epi cytoxazone via chiral bronsted acid-Rh2(OAc)4 co-catalyzed enantioselective three-component reactions. Journal of Organic Chemistry, 75, 7483-7486.
69. Fang, W.-S., Fang, Q.-C., Liang, X.-T. (2001). Synthesis of the 2a-benzoylamido analogue of docetaxel. Tetrahedron Letters, 42, 1331-1333.
70. Yuan, H., Fairchild, C.R., Liang, X., Kingston, D.G.I. (2000). Synthesis and biological activity of C-6 and C-7 modified paclitaxels. Tetrahedron, 56, 6407-6414.
71. Cheng, Q., Oritani, T., Horiguchi, T., Yamada, T., Mong, Y. (2000). Synthesis and biological evaluation of novel 9-functional heterocyclic coupled 7-deoxy-9-dihydropaclitaxel analogue. Bioorganic and Medicinal Chemistry Letters, 10, 517-521.
72. Danieli, B., Giardini, A., Lesma, G., Passarella, D., Silvani, A., Appendino, G., Noncovich, A., Fontana, G., Bombardelli, E., Sterner, O. (2004). Synthesis and biological evaluation of paclitaxel-thiocolchicine hybrids. Chemistry and Biodiversity, 1, 327-345.
73. Mellado,W., Magri, N.F., Kingston, D.G.I., Garcia-Arenas, R., Orr, G.A., Horwitz, S.B. (1984). Preparation and biological activity of taxol acetates. Biochemical and Biophysical Research Communication, 124, 329-336.
74. Xue, M., Long, B.H., Fairchild, C., Johnston, K., Rose,W.C., Kadow, J.F., Vyas, D.M., Chen, S.-H. (2000). Structure-activity relationships study at the 30-N position of paclitaxel. Part 2: Synthesis and biological evaluation of 30-N-thiourea-and 30-Nthiocarbamate-bearing paclitaxel analogues. Bioorganic and Medicinal Chemistry Letters, 10, 1327-1331.
75. Karliga, B., Schilling, J.K., Kingston, D.G.I., Bane, S., Ravindra, R., Talinli, N. (2006). Synthesis and biological evaluation of N-debenzoyl-N-(arylthio)carbonyl paclitaxel derivatives. Chemistry and Biodiversity, 3, 396-404.
76. Gelmon, K.A., Latreille, J., Tolcher, A., Genier, L., Fisher, B., Forand, D., D'Aloisio, S., Vernillet, L., Daigneault, L., Lebecq, A., Besenval, M., Eisenhauer, E. (2000). Phase I dose-finding study of a new taxane, RPR 109881A, administered as a one-hour intravenous infusion days 1 and 8 to patients with advanced solid tumors. Journal of Clinical Oncology, 18, 4098-4108.
77. Mita, A.C., Denis, L.J., Rowinsky, E.K., Debono, J.S., Goetz, A.D., Ochoa, L., Forouzesh, B., Beeram, M., Patnaik, A., Molpus, K., Semiond, D., Besenval, M., Tolcher, A.W. (2009). Phase I and pharmacokinetic study of XRP6258 (RPR116258A), a novel taxane, administered as a 1-hour infusion every 3 weeks in patients with advanced solid tumors. Clinical Cancer Research, 15, 723-730.
78. Pivot, X., Koralewski, P., Hidalgo, J.L., Chan, A., Goncalves, A., Schwartsmann, G., Assadourian, S., Lotz, J.P. (2008). A multicenter phase II study of XRP6258 administered as a 1-h i.v. infusion every 3 weeks in taxane-resistant metastatic breast cancer patients. Annals of Oncology, 19, 1547-1552.
79. Pivot, X., Asmar, L., Buzdar, A.U.,Valero,V., Hortobagyi, G. (2000).Aunified definition of clinical anthracycline resistance breast cancer. British Journal of Cancer, 83, 529-534.
80. Engels, F.K., Sparreboom, A., Mathot, R.A., Verweij, J. (2005). Potential for improvement of docetaxel-based chemotherapy: A pharmacological review. British Journal of Cancer, 93, 173-177.
81. Cisternino, S., Bourasset, F., Archimbaud, Y., Semiond, D., Sanderink, G., Sherrmann, J.-M. (2003). Nonlinear accumulation in the brain of the new taxoid TXD258 following saturation of P-glycoprotein at the blood-brain barrier in mice and rats. British Journal of Pharmacology, 138, 1367-1375.
82. Dykes, D.J., Sarsat, J.P., Bissery, M.C., Efficacy evaluation of TXD258, a taxoid compound against orthotopic and subcutaneous glioblastomas. In: Proceeding of the 91th American Association for Cancer Research, San Francisco, CA, 2000.
83. Brooks, T., Minderman, H., O'Loughlin, K.L., Pera, P., Ojima, I., Baer, M.R., Bernacki, R.J. (2003). Taxane-based reversal agents modulate drug resistance mediated by P-glycoprotein, multidrug resistance protein, and breast cancer resistance protein. Molecular Cancer Therapeutics, 2, 1195-1205.
84. Bissery, M.-C., Bouchard, H., Riou, J.F., Vrignaud, P., Combeau, C., Bourzat, J.D., Commercon, A., Lavelle, F. (2000). Preclinical evaluation of TXD258, a new taxoid. Proceedings of the American Association for Cancer Research, 41, 214.
85. Sessa, C., Cuvier, C., Caldiera, S., Bauer, J., Van den Bosch, S., Monnerat, C., Semiond, D., Perard, D., Lebecq, A., Besenval, M., Marty, M. (2002). Phase I clinical and pharmacokinetic studies of the taxoid derivative RPR109881A administered as a 1-hour or 3-hour infusion in patients with advanced solid tumors. Annals of Oncology, 13, 1140-1150.
86. Vrignaud, P., Lejeune, P., Bissery, M.C., In vivo synergy between doxorubicin, cisplatin or vinorelbine and RPR109881A, a newtaxoid. In: Procedings of the 96th Annual AACR Meeting, Anaheim, CA, 2005.
87. Vrignaud, P., Chiron, M., Stackhouse, M.A., Zuany-Amorim, C., Goulaouic, H., Bissery, M.C. In vivo synergy between trastuzumab (Herceptin) and larotaxel (RPR109881A), a new taxoid. In: Proceedings of the 98th Annual AACR Meeting, Los Angeles, CA, 2007.
88. Galsky, M.D., Dritselis, A., Kirkpatrick, P., Oh, W.K. (2010). Cabazitaxe. Nature Reviews Drug Discovery, 9, 677.
89. Mastalerz, H., Cook, D., Fairchild, C.R., Hansel, S., Johnson,W., Kadow, J.F., Long, B.-H., Rose,W.C., Tarrant, J.,Wu, M.-J., Xue, M.Q., Zhang, G., Zoeckler, M., Vyas, D.M. (2003). The discovery of BMS-275183: An orally efficacious novel taxane. Bioorganic and Medicinal Chemistry, 11, 4315-4323.
90. Br€oker, L.E., Veltkamp, S.A., Heath, E.I., Kuenen, B.C., Gall, H., Astier, L., Parker, S., Kayitalire, L., Lorusso, P.M., Schellens, J.H., Giaccone, G. (2007). A phase I safety and pharmacologic study of a twice weekly dosing regimen of the oral taxane BMS-275183. Clinical Cancer Research, 13, 3906-3912.
91. Rose, W.C., Long, B.H., Fairchild, C.R., Lee, F.Y.F., Kadow, J.F. (2001). Preclinical pharmacology of BMS-275183, an orally active taxane. Clinical Cancer Research, 7, 2016-2021.
92. Zhang, D., Ly, V.T., Lago, M., Tian, Y., Gan, J., Humphreys, W.G., Comezoglu, S.N. (2009). CYP3A4-mediated ester cleavage as the major metabolic pathway of the oral taxane 30-tert-butyl-30-N-tert-butyloxycarbonyl-4-deacetyl-30-dephenyl-30-Ndebenzoyl-4-O-methoxycarbonyl-paclitaxel (BMS-275183). Drug Metabolism and Disposition, 37, 710-718.
93. Ly, V.T., Caceres-Cortes, J., Zhang, D., Humphreys, W.G., Ekhato, I.V., Everett, D., Comezoglu, S.N. (2009). Metabolism and excretion of an oral taxane analog, [14C] 30-tert-butyl-30-N-tert-butyloxycarbonyl-4-deacetyl-30-dephenyl-30-N-debenzoyl-4-O-methoxycarbonyl-paclitaxel (BMS-275183), in rats and dogs. Drug Metabolism and Disposition, 37, 1115-1128.
94. Lockhart, A.C., Bukowski, R., Rothenberg, M.L., Wang, K.K., Cooper, W., Grover, J., Appleman, L., Mayer, P.R., Shapiro, M., Zhu, A.X. (2007). Phase I trial of oralMAC-321 in subjects with advanced malignant solid tumors. Cancer Chemotherapy and Pharmacology, 60, 203-209.
95. Ramanathan Ramesh, K., Picus, J., Raftopoulos, H., Bernard, S., Lockhart, A.C., Frenette, G., Macdonald, J., Melin, S., Berg, D., Brescia, F., Hochster, H., Cohn, A. (2008). A phase II study of milataxel: A novel taxane analogue in previously treated patients with advanced colorectal cancer. Cancer Chemotherapy and Pharmacology, 61, 453-458.
96. Dumontet, C., Sikic, B.I. (1999). Mechanisms of action of and resistance to antitubulin agents: Microtubule dynamics, drug transport, and cell death. Journal of Clinical Oncology, 17, 1061-1070.
97. Sampath, D., Discafani, C.M., Loganzo, F., Beyer, C., Liu, H., Tan, X., Musto, S., Annable, T., Gallagher, P., Rios, C., Greenberger, L.M. (2003).MAC-321, a novel taxane with greater efficacy than paclitaxel and docetaxel in vitro and in vivo. Molecular Cancer Therapeutics, 2, 873-884.
98. Safarpour, H., Connolly, P., Tong, X., Bielawski, M., Wilcox, E. (2009). Overcoming extractability hurdles of a 14C labeled taxane analogue milataxel and its metabolite from xenograft mouse tumor and brain tissues. Journal of Pharmaceutical and Biomedical Analysis, 49, 774-779.
99. Ramanathan, R.K., Picus, J., Raftopoulos, H., Bernard, S., Lockhart, A.C., Frenette, G., Macdonald, J., Melin, S., Berg, D., Brescia, F., Hochster, H., Cohn, A. (2008). A phase II study of milataxel: Anovel taxane analogue in previously treated patients with advanced colorectal cancer. Cancer Chemotherapy and Pharmacology, 61, 453-458.
100. Rose,W.C., Fairchild, C., Lee, F.Y.F. (2001). Preclinical antitumor activity of two novel taxanes. Cancer Chemotherapy and Pharmacology, 47, 97-105.
101. Fishman, M.N., Garrett, C.R., Simon, G.R., Chiappori, A.A., Lush, R.M., Dinwoodie, W.R., Manhany, J.J., Dellaportas, A.M., Cantor, A., Gollerki, A., Cohen, M.B., Sullivan, D.M. (2006). Phase I study of the taxane BMS-188797 in combination with carboplatin administered every 3 weeks in patients with solid malignancies. Clinical Cancer Research, 12, 523-528.
102. Advani, R., Fisher, G.A., Lum, B.L., Jambalos, C., Cho, C.D., Cohen, M., Gollerkeri, A., Sikic, B.I. (2003). Phase I and pharmacokinetic study of BMS-188797, a new taxane analog, administered on a weekly schedule in patients with advanced malignancies. Clinical Cancer Research, 9, 5187-5194.
103. du Bois, A., Jung, B., Loehr, A., Schaller-Kranz, T., Cohen, M., Frickhofen, N. (2006).A phase I and pharmacokinetic study of novel taxane BMS-188797 and cisplatin in patients with advanced solid tumours. British Journal of Cancer, 94, 79-84.
104. Garrett, C.R., Fishman, M.N., Rago, R.R., Williams, C.C., Dellaportas, A.M., Mahany, J.J., Lush, R.M., Dalton, W.S., Gollerkeri, A., Cohen, M.B., Sullivan, D.M. (2005). Phase I study of a novel taxane BMS-188797 in adult patients with solid malignancies. Clinical Cancer Research, 11, 3335-3341.
105. Kim, J., Amorino, G.P., Pyo, H., Cao, Q., Price, J.O., Choy, H. (2001). The novel taxane analogs, BMS-184476 and BMS-188797, potentiate the effects of radiation therapy in vitro and in vivo against human lung cancer cells. International Journal of Radiation Oncology, Biology, Physics, 51, 525-534.
106. Plummer, R., Ghielmini, M., Calvert, P., Voi, M., Renard, J., Gallant, G., Gupta, E., Calvert, H., Sessa, C. (2002). Phase I and pharmacokinetic study of the new taxane analog BMS-184476 given weekly in patients with advanced malignancies. Clinical Cancer Research, 8, 2788-2797.
107. Camps, C., Felip, E., Sanchez, J.M., Massuti, B., Artal, A., Paz-Ares, L., Carrato, A., Alberola,V., Blasco, A., Baselga, J., Astier, L.,Voi, M., Rosell, R. (2005). Phase II trial of the novel taxane BMS-184476 as second-line in non-small-cell lung cancer. Annals of Oncology, 16, 597-601.
108. Roche, M., Kyriakou, H., Serden, M. (2006). Drug evaluation: tese taxel-an oral Semisynthetic taxane derivative. Current Opinion Investigational Drugs, 7, 1092-1099.
109. Hwang, J.J., Marshall, J.L., Malik, S., Chun, H., Ahmed, T., Pilia, P.A. (2006). A Q7D phase I study of TPI 287, a novel taxane, in advanced malignancies: Imaging studies, pharmacokinetics (PK) and circulating tumor cell (CTC) quantitation. Journal of Clinical Oncology, 24, 12008.
110. Beer, M., Lenaz, L., Amadori, D. (2008). Phase II study of ortataxel in taxane-resistant breast cancer. Journal of Clinical Oncology, 26, Abstract 1066.
111. Iimura, S., Uoto, K., Ohsuki, S., Chiba, J., Yoshino, T., Iwahana, M., Jimbo, T., Terasawa, H., Soga, T. (2001). Orally active docetaxel analogue: Synthesis of 10-deoxy-10-C-morpholinoethyl docetaxel analogues. Bioorganic and Medicinal Chemistry Letters, 11, 407-410.
112. Ishiyama, T., Iimura, S., Ohsuki, S., Uoto, K., Terasawa, H., Soga, T. (2002). Newhighly active taxoids from 9b-dihydrobaccatin-9,10-acetals. Bioorganic and Medicinal Chemistry Letters, 12, 1083-1086.
113. Ishiyama, T., Iimura, S., Yoshino, T., Chiba, J., Uoto, K., Terasawa, H., Soga, T. (2002). Newhighly active taxoids from 9b-dihydrobaccatin-9,10-acetals: Part 2. Bioorganic and Medicinal Chemistry Letters, 12, 2815-2819.
114. Takeda, Y., Yoshino, T., Uoto, K., Chiba, J., Ishiyama, T., Iwahana, M., Jimbo, T., Tanaka, N., Terasawa, H., Soga, T. (2003). New highly active taxoids from 9bdihyrobaccatin-9,10-acetals: Part 3. Bioorganic and Medicinal Chemistry Letters, 13, 185-190.
115. Takeda, Y., Uoto, K., Chiba, J., Horiuchi, T., Iwahana, M., Atsumi, R., Ono, C., Terasawa, H., Soga, T. (2003). New highly active taxoids from 9b-dihydrobaccatin-9,10-acetals: Part 4. Bioorganic and Medicinal Chemistry Letters, 11, 4431-4447.
116. Takeda,Y., Uoto, K., Iwahana, M., Jimbo,T., Nagata, M., Atsumi, R., Ono, C.,Tanaka, N., Terasawa, H., Soga, T. (2004). Newhighly active taxoids from 9b-dihydrobaccatin-9,10-acetals: Part 5. Bioorganic and Medicinal Chemistry Letters, 14, 3209-3215.
117. Carmeliet, P., Jain, R.K. (2000). Angiogenesis in cancer and other diseases. Nature, 407, 249-257.
118. Brower, V. (1999). Tumor angiogenesis -New drugs on the block. Nature Biotechnology, 17, 963-968.
119. Giavazzi, R., Taraboletti, G. (1999). Angiogenesis and angiogenesis inhibitors in cancer. Forum-(Genova), 9, 261-272.
120. Taraboletti, G., Micheletti, G., Rieppi, M., Poli, M., Turatto, M., Rossi, C., Borsotti, P., Roccabianca, P., Scanziani, E., Nicoletti, M. I., Bombardelli, E., Morazzoni, P., Riva, A., Giavazzi, R. (2002). Antiangiogenic and antitumor activity of IDN 5390, a new taxane derivative. Clinical Cancer Research, 8, 1182-1188.
121. Pratesi, G., Laccabue, D., Lanzi, C., Cassinelli, G., Supino, R., Zucchetti, M., Frapolli, R., D'Incalci, M., Bombardelli, E., Morazzoni, P., Riva, A., Zunino, F. (2003). IDN 5390: An oral taxane candidate for protracted treatment schedules. British Journal of Cancer, 88, 965-972.
122. Frapolli, R., Marangon, E., Zaffaroni, M., Colombo, T., Falcioni, C., Bagnati, R., Simone, M., D'Incalci, M., Manzotti, C., Fontana, G., Morazzoni, P., Zucchetti, M. (2006). Pharmacokinetics and metabolism in mice of IDN 5390 (13-(N-Boc-3-i-butylisoserinoyl)-C-7,8-seco-10-deacetylbaccatin III), a new oral C-seco-taxane derivative with antiangiogenic property effective on paclitaxel-resistant tumors. Drug Metabolism and Disposition, 34, 2028-2035.
123. Ferlini, C., Raspaglio, G., Mozzetti, S., Cicchillitti, L., Filippetti, F., Gallo, D., Gattorusso, C., Campiani, G., Scambia, G. (2005). The seco-taxane IDN5390 is able to target class III b-tubulin and to overcome paclitaxel resistance. Cancer Research, 65, 2397-2405.
124. Dubois, J., Thoret, S., Gueritte, F., Guenard, D. (2000). Synthesis of 5(20)deoxydocetaxel, a new active docetaxel analogue. Tetrahedron Letters, 41, 3331-3334.
125. Merckle, L., Dubois, J., Place, E., Thoret, S., Gueritte, F., Guenard, D., Poupat, C., Ahond, A., Potier, P. (2001). Semisynthesis of D-ring modified taxoids: Novel thia derivatives of docetaxel. Journal of Organic Chemistry, 66, 5058-5065.
126. Gunatilaka, A.A.L., Ramdayal, F.D., Sarragiotto, M.H., Kingston, D.G.I., Sackett, D.L., Hamel, E. (1999). Synthesis and biological evaluation of novel paclitaxel (taxol) D-ring modified analogues. Journal of Organic Chemistry, 64, 2694-2703.
127. Battaglia, A., Bernacki, R.J., Bertucci, C., Bombardelli, E., Cimitan, S., Ferlini, C., Fontana, G., Guerrini, A., Riva, A. (2003). Synthesis and biological evaluation of 20-methyl taxoids derived from baccatin III and 14b-OH-baccatin III 1,14-carbonate. Journal of Medicinal Chemistry, 46, 4822-4825.
128. Liu, C., Tamm, M., Notzel, M.W., de Meijere, A., Schilling, J.K., Kingston, D.G.I. (2003). Synthesis and bioactivities of paclitaxel analogs with a cyclopropanated sidechain. Tetrahedron Letters, 44, 2049-2052.
129. Barboni, L., Ballini, R., Giarlo, G., Appendino, G., Fontana, G., Bombardelli, E. (2005). Synthesis and biological evaluation of methoxylated analogs of the newer generation taxoids IDN5109 and IDN5390. Bioorganic and Medicinal Chemistry Letters, 15, 5182-5186.
130. Chaudhary, A.G., Gharpure, M.M., Rimoldi, J.M., Chordia, M.D., Gunatilaka, A.A.L., Kingston, D.G.I., Grover, S., Lin, C.M., Hamel, E. (1994). Unexpectedly facile hydrolysis of the 2-benzoate group of taxol and synthesis of analogs with increased activities. Journal of the American Chemical Society, 116, 4097-4098.
131. Kuznetsova, L., Chen, J., Sun, L.,Wu, X., Pepe, A., Veith, J. M., Pera, P., Bernacki, R.J., Ojima, I. (2006). Syntheses and evaluation of novel fatty acid-second-generation taxoid conjugates as promising anticancer agents. Bioorganic and Medicinal Chemistry Letters, 16, 974-977.
132. Ferjancic, Z., Matovic, R., Cekovic, Z., Jiang,Y., Snyder, J.P., Trajkovic,V., Saicic, R.N. (2006). Synthesis, biology, and modeling of a C-4 carbonyl C,D-seco-taxoid. Tetrahedron, 62, 8503-8514.
133. Ojima, I.,Kuznetsova,L.V.,Sun, L.,Organofluorinechemistry at the biomedical interface: A case study on fluoro-taxoid anticancer agents. In: Soloshonok, V.A., Mikami, K., Yamazaki,T.,Welch, J.T.,Honek, J., editors. Current Fluoroorganic Chemistry,Vol. 949, American Chemical Society, Stony Brook, NY, USA, 2007, pp. 288-304.
134. Mikuni, K., Nakanishi, K., Hara, K., Hara, K., Iwatani, W., Amano, T., Nakamura, K., Tsuchiya, Y., Okumoto, H., Mandai, T. (2008). In vivo antitumor activity of novel watersoluble taxoids. Biological and Pharmaceutical Bulletin, 31, 1155-1158.
135. Ojima, I., Chen, J., Sun, L., Borella, C.P., Wang, T., Miller, M.L., Lin, S., Geng, X., Kuznetsova, L., Qu, C., Gallager, D., Zhao, X., Zanardi, I., Xia, S., Horwitz, S.B., Mallen-St. Clair, J., Guerriero, J.L., Bar-Sagi, D., Veith, J.M., Pera, P., Bernacki, R.J. (2008). Design, synthesis, and biological evaluation of new-generation taxoids. Journal of Medicinal Chemistry, 51, 3203-3221.
136. Ke, B., Qin, Y., Zhao, F., Qu, Y. (2008). Synthesis and biological evaluation of novel 30-N-tert-butylsulfonyl analogues of docetaxel. Bioorganic and Medicinal Chemistry Letters, 18, 4783-4785.
137. Kuznetsova, L.V., Pepe, A., Ungureanu, I.M., Pera, P., Bernacki, R.J., Ojima, I. (2008). Syntheses and structure-activity relationships of novel 30-difluoromethyl and 30-trifluoromethyl-taxoids. Journal of Fluorine Chemistry, 129, 817-828.
138. Pepe, A., Sun, L., Zanardi, I.,Wu, X., Ferlini, C., Fontana, G., Bombardelli, E., Ojima, I. (2009). Novel C-seco-taxoids possessing high potency against paclitaxel-resistant cancer cell lines overexpressing class III b-tubulin. Bioorganic and Medicinal Chemistry Letters, 19, 3300-3304.
139. Lu, H., Sun, X., Xu, L., Lou, L., Lin, G. (2009). Design, synthesis and biological evaluation of novel fluorinated docetaxel analogues. European Journal of Medicinal Chemistry, 44, 482-491.
140. Holton, R.A. (1992: 29 Dec). Method for Preparation of Taxol Using b-lactam. Florida State University, US. US Patent 5175315.
141. Exposito, O., Bonfill, M., Moyano, E., Onrubia, M., Mirjalili, M.H., Cusido, R.M., Palazon, J. (2009). Biotechnological production of taxol and related taxoids: Current state and prospects. Anti-Cancer Agents in Medicinal Chemistry, 9, 109-121.
142. Available at http://www.genexol.com/eng/app//manufacture/default.asp.
143. Rao, S., Krauss, N.E., Heerding, J.M., Swindell, C.S., Ringel, I., Orr, G.A., Horwitz, S.B. (1994). 30-(p-Azidobenzamido)taxol photolabels the N-terminal 31 amino acids of b-tubulin. Journal of Biological Chemistry, 269, 3132-3134.
144. Rao, S., Orr, G.A., Chaudhary, A.G., Kingston, D.G.I., Horwitz, S.B. (1995). Characterization of the taxol binding site on the microtubule. Journal of Biological Chemistry, 270, 20235-20238.
145. Nogales, E., Wolf, S.G., Downing, K.H. (1998). Structure of the ab tubulin dimer by electron crystallography. Nature 39, 199-203.
146. Lowe, J., Li, H., Downing, K.H., Nogales, E. (2001). Refined structure of b-tubulin at 3.5 A resolution. Journal of Molecular Biology, 313, 1045-1057.
147. Dubois, J., Guenard, D., Gueritte-Voeglein, F., Guedira, N., Potier, P., Gillet, B., Betoeil, J.-C. (1993). Conformation of taxotere and analogues determined by NMR spectroscopy and molecular modeling studies. Tetrahedron, 49, 6533-6544.
148. Ojima, I., Kuduk, S.D., Chakravarty, S., Ourevitch, M., Begue, J.-P. (1997). A novel approach to the study of solution structures and dynamic behavior of paclitaxel and docetaxel using fluorine-containing analogs as probes. Journal of the American Chemical Society, 119, 5519-5527.
149. Williams, H.J., Scott, A.I., Dieden, R.A., Swindell, C.S., Chirlian, L.E., Francl, M.M., Heerding, J.M., Krauss, N.E. (1993). NMR and molecular modeling study of the conformations of taxol and of its side chain methylester in aqueous and non-aqueous solution. Tetrahedron, 49, 6545-6560.
150. Milanesio, M., Ugliengo, P., Viterbo, D. (1999). Ab initio conformational study of the phenylisoserine side chain of paclitaxel. Journal of Medicinal Chemistry, 42, 291-299.
151. Vander Velde, D.G., Georg, G.I., Grunewald, G.L., Gunn, C.W., Mitscher, L.A. (1993). "Hydrophobic collapse" of Taxol and Taxotere solution conformations in mixtures of water and organic solvent. Journal of theAmerican Chemical Society, 115, 11650-11651.
152. Snyder, J.P., Nettles, J.H., Cornett, B., Downing, K.H., Nogales, E. (2001). The binding conformation of taxol in b-tubulin: A model based on electron crystallographic density. Proceedings of the National Academy of Sciences of the U.S.A., 98, 5312-5316.
153. Kingston, D.G.I., Bane, S., Snyder, J.P. (2005). The taxol pharmacophore and the T-taxol bridging principle. Cell Cycle, 4, 279-289.
154. Snyder, J.P., Nevins, N., Cicero, D.O., Jansen, J. (2000). The conformations of taxol in chloroform. Journal of the American Chemical Society, 122, 724-725.
155. Gueritte-Voegelein, F., Guenard, D., Mangatal, L., Potier, P., Guilhem, J., Cesario, M., Pascard, C. (1990). Structure of a synthetic taxol precursor: N-tert-butoxycarbonyl-10-deacetyl-N-debenzoyltaxol. Acta Crystallographica, C46, 781-784.
156. Mastropaolo, D., Camerman, A., Luo, Y., Brayer, G.D., Camerman, N. (1995). Crystal and molecular structure of paclitaxel (Taxol). Proceedings of the National Academy of Sciences of the U.S.A., 92, 6920-6924.
157. Williams, H.J., Moyna, G., Scott, A.I., Swindell, C.S., Chirlian, L.E., Heerding, J.M., Williams, D.K. (1996). NMR and molecular modeling study of the conformations of taxol 20-acetate in chloroform and aqueous dimethyl sulfoxide solutions. Journal of Medicinal Chemistry, 39, 1555-1559.
158. Chmurny, G.N., Hilton, B.D., Brobst, S., Look, S.A., Witherup, K.M., Beutler, J.A. (1992). 1H-and 13C-NMR assignments for Taxol, 7-epi-Taxol, and Cephalonannine. Journal of Natural Products, 55, 414-423.
159. Geney, R., Sun, L., Pera, P., Bernacki, R.J., Xia, S., Horwitz, S.B., Simmerling, C.L., Ojima, I. (2005). Use of the tubulin bound paclitaxel conformation for structure-based rational drug design. Chemical Biology, 12, 339-348.
160. Li, Y., Poliks, B., Cegelski, L., Poliks, M., Cryczynski, Z., Piszczek, G., Jagtap, P.,G., Studelska, D.R., Kingston, D.G.I., Schaefer, J., Bane, S. (2000). Conformation of microtubule-bound paclitaxel determined by fluorescence spectroscopy and REDOR NMR. Biochemistry, 39, 281-291.
161. Gao, Q., Wei, J.-M., Chen, S.-H. (1995). Crystal structure of 2-debenzoyl, 2-acetoxy paclitaxel (Taxol): Conformation of the paclitaxel side-chain. Pharmaceutical Research, 12, 337-341.
162. Gao, Q., Chen, S.-H. (1996). An unprecedented side chain conformation of paclitaxel (Taxol): Crystal structure of 7-mesylpaclitaxel. Tetrahedron Letters, 37, 3425-3428.
163. Cachau, R.E., Gussio, R., Beutler, J.A., Chmurny, G.N., Hilton, B.D., Muschik, G.M., Erickson, J.W. (1994). Solution structure of taxol determined using a novel feedbackscaling procedure for NOE-restrained molecular dynamics. International Journal of High Performance Computing Applications, 8, 24-34.
164. Paloma, L.G., Guy, R.K., Wrasidlo,W., Nicolaou, K.C. (1994). Conformation of a watersoluble derivative of taxol in water by 2D-NMR spectroscopy. Chemical Biology, 1, 107-112.
165. Park, Y., Yang, C., Metaferia, B., Tang, S., Bane, S., Ravindra, R., Shanker, N., Alcaraz, A.A., Johnson, S.A., Schaefer, J., O'Connor, R.D., Cegeleski, L., Snyder, J.P., Kingston, D.G.I. (2007). Rotational-echo double-resonance NMR distance measurements for the tubulin-bound paclitaxel conformation. Journal of the American Chemical Society, 129, 361-370.
166. Rao, S., He, L., Chakravarty, S., Ojima, I., Orr, G.A., Horwitz, S.B. (1999). Characterization of the taxol binding site on the microtubule. Journal of Biological Chemistry, 274, 37990-37994.
167. Sun, L., Simmerling, C., Ojima, I. (2009). Recent advances in the study of the bioactive conformation of taxol. Chem Med Chem, 4, 719-731.
168. Yang, Y., Alcaraz, A.A., Snyder, J.P. (2009). The tubulin-bound conformation of paclitaxel: T-taxol vs "PTX-NY". Journal of Natural Products, 72, 422-429.
169. Ivery, M.T., Le, T. (2003). Modeling the interaction of paclitaxel with b-tubulin. Oncology Research, 14, 1-19.
170. Metaferia, B.B., Hoch, J., Glass, T.E., Bane, S.L., Chatterjee, S.K., Snyder, J.P., Lakdawala, A., Cornett, B., Kingston, D.G.I. (2001). Synthesis and biological evaluation of novel macrocyclic paclitaxel analogues. Organic Letters, 3, 2461-2464.
171. Ganesh, T., Guza, R.C., Bane, S., Ravindra, R., Shanker, N., Lakdawala, A.S., Snyder, J.P., Kingston, D.G.I. (2004). The bioactive taxol conformation on b-tubulin: Experimental evidence from highly active constrained analogs. Proceedings of the National Academy of Sciences of the U.S.A., 101, 10006-10011.
172. Barboni, L., Lambertucci, C., Appendino, G., Vander Velde, D.G., Himes, R.H., Bombardelli, E., Wang, M., Snyder, J.P. (2001). Synthesis and NMR-driven conformational analysis of taxol analogues conformationally constrained on the C13 side chain. Journal of Medicinal Chemistry, 44, 1576-1587.
173. Boge, T.C., Wu, Z.-J., Himes, R.H., Vander Velde, D.G., Georg, G.I. (1999). Conformationally restricted paclitaxel analogues: Macrocyclic mimics of the "hydrophobic collapse" conformation. Bioorganic and Medicinal Chemistry Letters, 9, 3047-3052.
174. Chakravarty, S., Lin, S., Inoue, T., Horwitz, S.B., Kuduk, S.D., Danishefsky, S.J., Ojima, I., A common pharmacophore for cytotoxic microtubule-stabilizing agents: Interpretation of SAR studies. In: 217th ACS National Meeting, Anaheim, CA, 1999.
175. Ojima, I., Lin, S., Inoue, T., Miller, M.L., Borella, C.P., Geng, X., Walsh, J.J. (2000). Macrocycle formation by ring-closing metathesis. Application to the syntheses of novel macrocyclic taxoids. Journal of the American Chemical Society, 122, 5343-5353.
176. Ojima, I., Geng, X., Lin, S., Pera, P., Bernacki, R.J. (2002). Design, synthesis and biological activity of novel C2-C30N-linked macrocyclic taxoids. Bioorganic and Medicinal Chemistry Letters, 12, 349-352.
177. Geng, X., Miller, M.L., Lin, S., Ojima, I. (2003). Synthesis of novel C2-C30N-linked macrocyclic taxoids by means of highly regioselective Heck macrocyclization. Organic Letters, 5, 3733-3736.
178. Querolle, O., Dubois, J., Thoret, S., Dupont, C., Gueritte, F., Guenard, D. (2003). Synthesis of novel 2-O,30-N-linked macrocyclic taxoids with variable ring size. European Journal of Organic Chemistry, 2003, 542-550.
179. Querolle, O., Dubois, J., Thoret, S., Roussi, F., Montiel-Smith, S., Gueritte, F., Guenard, D. (2003). Synthesis of novel macrocyclic docetaxel analogues. Influence of their macrocyclic ring size on tubulin activity. Journal of Medicinal Chemistry, 46, 3623-3630.
180. Querolle, O., Dubois, J., Thoret, S., Roussi, F., Guéritte, F., Guénard, D. (2004). Synthesis of C2-C30N-linked macrocyclic taxoids. Novel docetaxel analogues with high tubulin activity. Journal of Medicinal Chemistry, 47, 5937-5944.
181. Blechert, S., Kleine-Klausing, A. (1991). Synthesis of a biologically active taxol analogue. Angewndte Chemie International Edition, 30, 412-414.
182. Blechert, S., Jansen, R., Velder, J. (1994). Synthesis of new taxoids. Tetrahedron, 50, 9649-9656.
183. Senilh, V., Gueritte, F., Guenard, D., Colin, M., Potier, P. (1984). Hemisynthese de nouveaux analogues du taxol. Etude de leur interaction avec la tubuline. Comptesrendus des Séances de l'Académie de Sciences, 299, 1039-1043.
184. Kingston, D.G.I., Hawkins, D.R., Ovington, L. (1982). New taxanes from Taxus brevifolia. Journal of Natural Products, 45, 466-470.
185. Klar, U., Graf, H., Schenk, O., Rohr, B., Schulz, H. (1998). New synthetic inhibitors of microtubule depolymerization. Bioorganic and Medicinal Chemistry Letters, 8, 1397-1402.
186. Almqvist, F., Manner, S., Thornqvist, V., Berg, U., Wallin, M., Frejd, T. (2004). Spirobicyclo[2.2.2]octane derivatives: Mimetics of baccatin III and paclitaxel (Taxol). Organic and Biomolecular Chemistry, 2, 3085-3090.
187. Geng, X., Geney, R., Pera, P., Bernacki, J., Ojima, I. (2004). Design and synthesis of de novo cytotoxic alkaloids through mimicking taxoid skeleton. Bioorganic and Medicinal Chemistry Letters, 14, 3491-3494.
188. Ganesh, T., Norris, A., Sharma, S., Bane, S., Alcaraz, A.A., Snyder, J.P., Kingston, D.G.I. (2006). Design, synthesis, and bioactivity of simplified paclitaxel analogs based on the Ttaxol bioactive conformation. Bioorganic and Medicinal Chemistry, 14, 3447-3454.
189. Zhao, J., Bane, S., Snyder, J.P., Hu, H., Kingston, D.G.I. (2011). Design and synthesis of simplified paclitaxel analogs based on the T-taxol bioactive conformation. Bioorganic and Medicinal Chemistry, 19, 7664-7678.
190. Sun, L., Veith, J.M., Pera, P., Bernacki, R.J., Ojima, I. (2010). Design and synthesis of de novo cytotoxic alkaloids by mimicking the bioactive conformation of paclitaxel. Bioorganic and Medicinal Chemistry, 18, 7101-7112.
191. Giannakakou, P., Sackett, D.L., Kang, Y.-K., Zhang, Z., Buters, J.T.M., Fojo, T., Poruchynsky, M.S. (1997). Paclitaxel-resistant human ovarian cancer cells have mutant b-tubulins that exhibit impaired paclitaxel-driven polymerization. Journal of Biological Chemistry, 272, 17118-17125.
192. Sharma, A., Mayhew, E., Bolcsak, L., Cavanaugh, C., Harmon, P., Janoff, A., Bernacki, R.J. (1997). Activity of paclitaxel liposome formulations against human ovarian tumor xenografts. International Journal of Cancer, 71, 103-107.
193. Michaud, L.B., Valero, V., Hortobagyi, G. (2000). Risks and benefits of taxanes in breast and ovarian cancer. Drug Safety, 23, 401-428.
194. Deutsch, H.M., Glinski, J.A., Hernandez, M., Haugwitz, R.D., Narayanan, V.L., Suffness, M., Zalkow, L.H. (1989). Synthesis of congeners and prodrugs: 3. Watersoluble prodrugs of taxol with potent antitumor activity. Journal of Medicinal Chemistry, 32, 788-792.
195. Zhao, Z., Kingston, D.G.I., Crosswell, A.R. (1991). Modified taxols, 6. Preparation of water-soluble prodrugs of taxol. Journal of Natural Products, 54, 1607-1611.
196. Mathew, A.E., Mejillano, M.R., Nath, J.P., Himes, R.H., Stella, V.J. (1992). Synthesis and evaluation of some water-soluble prodrugs and derivatives of taxol with antitumor activity. Journal of Medicinal Chemistry, 35, 145-151.
197. Vyas, D.M., Wong, H., Crosswell, A.R., Casazza, A.M., Knipe, J.O., Mamber, S.W., Doyle, T.W. (1993). Synthesis and antitumor evaluation of water soluble taxol phosphates. Bioorganic and Medicinal Chemistry Letters, 3, 1357-1360.
198. Ueda, Y., Mikkilineni, A.B., Knipe, J.O., Rose, W.C., Casazza, A.M., Vyas, D.M. (1993). Novel water soluble phosphate prodrugs of taxol possessing in vivo antitumor activity. Bioorganic and Medicinal Chemistry Letters, 3, 1761-1766.
199. Ueda, Y., Matiskella, J.D., Mikkilineni, A.B., Farina, V., Knipe, J.O., Rose, W.C., Casazza, A.M., Vyas, D.M. (1995). Novel, water-soluble phosphate derivatives of 20-ethoxy carbonylpaclitaxel as potential prodrugs of paclitaxel: Synthesis and antitumor evaluation. Bioorganic and Medicinal Chemistry Letters, 5, 247-252.
200. Golik, J.,Wong, H.S.L., Chen, S.-H., Doyle, T.W., Wright, J.J.K., Knipe, J., Rose,W.C., Casazza, A.M., Vyas, D.M. (1996). Synthesis and antitumor evaluation of paclitaxel phosphonooxymethyl ethers: A novel class of water soluble paclitaxel pro-drugs. Bioorganic and Medicinal Chemistry Letters, 6, 1837-1842.
201. Skwarczynski, M., Hayashi, Y., Kiso, Y. (2006). Paclitaxel prodrugs: Toward smarter delivery of anticancer agents. Journal of Medicinal Chemistry, 49, 7253-7269.
202. Ganesh, T. (2007). Improved biochemical strategies for targeted delivery of taxoids. Bioorganic and Medicinal Chemistry, 15, 3597-3623.
203. Safavy,A. (2008). Recent developments in taxane drug delivery. Current Drug Delivery, 5, 42-54.
204. Damen, E.W.P., Wiegerinck, P.H.G., Braamer, L., Sperling, D., de Vos, D., Scheeren, H.W. (2000). Paclitaxel esters of malic acid as prodrugs with improved water solubility. Bioorganic and Medicinal Chemistry, 8, 427-432.
205. Seligson, A.L., Terry, R.C., Bressi, J.C., Douglass, J.G., Sovak, M. (2001). A new prodrug of paclitaxel: Synthesis of protaxel. Anti-Cancer Drugs, 12, 305-313.
206. Shimoda, K., Hamada, H., Hamada, H. (2008). Chemo-enzymatic synthesis of esterlinked taxol-oligosaccharide conjugates as potential prodrugs. Tetrahedron Letters, 49, 601-604.
207. Kirschberg, T.A., VanDeusen, C.L., Rothbard, J.B., Yang, M., Wender, P.A. (2003). Arginin-based molecular transporters: The synthesis and chemical evaluation of releasable taxol-transporter conjugates. Organic Letters, 5, 3459-3462.
208. Futaki, S., Goto, S., Sugiura, Y. (2003). Membrane permeability commonly shared among arginine-rich peptides. Journal of Molecular Recognition, 16, 260-264.
209. Rothbard, J.B., Kreider, E., VanDeusen, C.L., Wright, L., Wylie, B.L., Wender, P.A. (2002). Arginine-rich molecular transporters for drug delivery: Role of backbone spacing in cellular uptake. Journal of Medicinal Chemistry, 45, 3612-3618.
210. Battaglia, A., Guerrini, A., Baldelli, E., Fontana, G., Varchi, G., Samori, C., Bombardelli, E. (2006). Synthesis of 7-and 10-spermine conjugates of paclitaxel and 10-deacetyl-paclitaxel as potential prodrugs. Tetrahedron Letters, 47, 2667-2670.
211. Moosavi-Movahedi, A.A., Hakimelahi, S., Chamani, J., Khodarahmi, G.A., Hassanzadeh, F., Luo, F.-T., Ly, T.W., Shia, K.-S., Yen, C.-F., Jain, M.L., Kulatheeswaran, R., Xue, C., Pasdar, M., Hakimelahi, G.H. (2003). Design, synthesis, and anticancer activity of phosphonic acid diphosphate derivative of adenine-containing butenolide and its water-soluble derivatives of paclitaxel with high antitumor activity. Bioorganic and Medicinal Chemistry, 11, 4303-4313.
212. Skwarczynski, M., Sohma, Y., Kimura, M., Hayashi, Y., Kimura, T., Kiso, Y. (2003). O-N Intramolecular acyl migration strategy in water-soluble prodrugs of taxoids. Bioorganic and Medicinal Chemistry, 13, 4441-4444.
213. de Groot, F.M.H., van Berkom, L.W.A., Scheeren, H.W. (2000). Synthesis and biological evaluation of 20-carbamate-linked and 20-carbonate-linked prodrugs of paclitaxel: Selective activation by the tumor-associated protease plasmin. Journal of Medicinal Chemistry, 43, 3093-3102.
214. Damen, E.W.P., Nevalainen, T.J., van den Bergh, T.J.M., de Groot, F.M.H., Scheeren, H.W. (2002). Synthesis of novel paclitaxel prodrugs designed for bioreductive activation in hypoxic tumour tissue. Bioorganic and Medicinal Chemistry, 10, 71-77.
215. Vrudhula, V.M., MacMaster, J.F., Li, Z., Kerr, D.E., Senter, P.D. (2002). Reductively activated disulfide prodrugs of paclitaxel. Bioorganic and Medicinal Chemistry Letters, 12, 3591-3594.
216. Liu, C., Strobl, J.S., Bane, S., Schilling, J.K., McCracken, M., Chatterjee, S.K., Rahim-Bata, R., Kingston, D.G.I. (2003). Design, synthesis, and bioactivities of steroid-linked taxol analogues as potential targeted drugs for prostate and breast cancer. Journal of Natural Products, 67, 152-159.
217. Park,W.-C., Jordan, V.C. (2002). Selective estrogen receptor modulators (SERMS) and their roles in breast cancer prevention. Trends in Molecular Medicine, 8, 82-88.
218. Lee, J.W., Lu, J.Y., Low, P.S., Fuchs, P.L. (2002). Synthesis and evaluation of taxol-folic acid conjugates as targeted antineoplastics. Bioorganic and Medicinal Chemistry, 10, 2397-2414.
219. Wang, S., Low, P.S. (1998). Folate-mediated targeting of antineoplastic drugs, imaging agents, and nucleic acids to cancer cells. Journal Controlled Release, 53, 39-48.
220. Chen, X., Plasencia, C., Hou,Y., Neamati, N. (2005). Synthesis and biological evaluation of dimeric RGD peptide-paclitaxel conjugate as a model for integrin-targeted drug delivery. Journal of Medicinal Chemistry, 48, 1098-1106.
221. Ryppa, C., Mann-Steinberg, H., Biniossek, M.L., Satchi-Fainaro, R., Kratz, F. (2009). In vitro and in vivo evaluation of a paclitaxel conjugate with the divalent peptide E-[c(RGDfK)2] that targets integrin avb3. International Journal of Pharmacy, 368, 89-97.
222. Bradley, M.O., Swindell, C.S., Anthony, F.H.,Witman, P.A., Devanesan, P.,Webb, N.L., Baker, S.D., Wolff, A.C., Donehower, R.C. (2001). Tumor targeting by conjugation of DHA to paclitaxel. Journal of Controlled Release, 74, 233-236.
223. Bradley, M.O., Webb, N.L., Anthony, F.H., Devanesan, P., Witman, P.A., Hemamalini, S., Chander, M.C., Baker, S.D., He, L., Horwitz, S.B., Swindell, C.S. (2001). Tumor targeting by covalent conjugation of a natural fatty acid to paclitaxel. Clinical Cancer Research, 7, 3229-3238.
224. Wolff, A.C., Donehower, R.C., Carducci, M.K., Carducci, M.A., Brahmer, J.R., Zabelina, Y., Bradley, M.O., Anthony, F.H., Swindell, C.S., Witman, P.A., Webb, N.L., Baker, S.D. (2003). Phase I study of docosahexaenoic acid-paclitaxel: A taxane-fatty acid conjugate with a unique pharmacology and toxicity profile. Clinical Cancer Research, 9, 3589-3597.
225. Lin, Y.-S., Tungpradit, R., Sinchaikul, S., An, F.-M., Liu, D.-Z., Phutrakul, S., Chen, S.-T. (2008). Targeting the delivery of glycan-based paclitaxel prodrugs to cancer cells via glucose transporters. Journal of Medicinal Chemistry, 51, 7428-7441.
226. Nguyen, X.C., Lee, W.W., Chung, J.H., Park, S.Y., Sung, S.W., Kim, Y.K., So, Y., Lee, D.S., Chung, J.K., Lee, M.C., Kim, S.E. (2007). FDG uptake, glucose transporter type 1, and Ki-67 expressions in non-small-cell lung cancer: Correlations and prognostic values. European Journal of Radiology, 62, 214-219.
227. Vrudhula, V.M., Kerr, D., Siemers, O., Dubowchik, G.M., Senter, P.D. (2003). Cephalosporin prodrugs of paclitaxel for immunologically specific activation by L-49-sFv-blactamase fusion protein. Bioorganic and Medicinal Chemistry Letters, 13, 539-542.
228. Bouvier, E., Thirot, S., Schmidt, F., Monneret, C. (2003). A new paclitaxel prodrug for use in ADEPT strategy. Organic and Biomolecular Chemistry, 1, 3343-3352.
229. Skwarczynski, M., Noguchi, M., Hirota, S., Sohma, Y., Kimura, T., Hayashi, Y., Kiso, Y. (2006). Development of first photoresponsive prodneg of paclitaxel. Bioorganic and Medicinal Chemistry Letters, 16, 4492-4496.
230. Ryu, B.-Y., Sohn, J.-S., Hess, M., Choi, S.-K., Choi, J.-K., Jo, B.-W. (2008). Synthesis and anti-cancer efficacy of rapid hydrolysed water-soluble paclitaxel pro-drugs. Journal of Biomaterials Science, Polymer Edition, 19, 311-324.
231. Kakinoki, A., Kaneo, Y., Tanaka, T., Hosokawa, Y. (2008). Synthesis and evaluation of water-soluble poly(vinyl alcohol)-paclitaxel conjugate as a macromolecular prodrug. Biological and Pharmaceutical Bulletin, 31, 963-969.
232. Meerum Terwogt, J.M., ten Bokkel Huinink, W.W., Schellens, J.H.M., Schot, M., Mandjes, I.A.M., Zurlo, M.G., Rocchetti, M., Rosing, H., Koopman, F.J., Beijnen, J.H. (2001). Phase I clinical and pharmacokinetic study of PNU166945, a novel watersoluble polymer-conjugated prodrug of paclitaxel. Anti-Cancer Drugs, 12, 315-323.
233. Erez, R., Segal, E., Miller, K., Satchi-Fainaro, R., Shabat, D. (2009). Enhanced cytotoxicity of a polymer-drug conjugate with triple payload of paclitaxel. Bioorganic and Medicinal Chemistry, 17, 4327-4335.
234. Rihova, B., Kubackova, K. (2003). Clinical implications of N-(2-hydroxy-propyl) methacrylamide copolymers. Current Pharmaceutical Biotechnology, 4, 311-322.
235. Singer, J.W. (2005). Paclitaxel poliglumex (XYOTAX(TM), CT-2103): A macromolecular taxane. Journal of Controlled Release 109, 120-126.
236. Veronese, M.L., Flaherty, K., Kramer, A., Konkle, B.A., Morgan, M., Stevenson, J.P., O'Dwyer, P.J. (2005). Phase I study of the novel taxane CT-2103 in patients with advanced solid tumors. Cancer Chemotherapy and Pharmacology, 55, 497-501.
237. Luo, Y., Ziebell, M.R., Prestwich, G.D. (2000). A hyaluronic acid-taxol antitumor bioconjugate targeted to cancer cells. Biomacromolecules, 1, 208-218.
238. Yeo, T., Nagy, J., Yeo, K., Dvorak, H., Toole, B. (1996). Increased hyaluronan at sites of attachment to mesentery by CD44-positive mouse ovarian and breast tumor cells. American Journal of Pathology, 148, 1733-1740.
239. Toole, B.P. (1997). Hyaluronan in morphogenesis. Journal of Internal Medicine, 242, 35-40.
240. Turley, E.A., Belch, A.J., Poppema, S., Pilarsk, L.M. (1993). Expression and function of a receptor for hyaluronan-mediated motility on normal and malignant B lymphocytes. Blood, 81, 446-453.
241. Lee, E., Lee, J., Lee, I.-H., Yu, M., Kim, H., Chae, S.Y., Jon, S. (2008). Conjugated chitosan as a novel platform for oral delivery of paclitaxel. Journal of Medicinal Chemistry, 51, 6442-6449.
242. Majoros, I.J., Myc, A., Thomas, T., Mehta, C.B., Baker, J.R. (2006). PAMAM dendrimer-based multifunctional conjugate for cancer therapy: Synthesis, characterization, and functionality. Biomacromolecules, 7, 572-579.
243. Paciotti, G.F., Kingston, D.G.I., Tamarkin, L. (2006). Colloidal gold nanoparticles: A novel nanoparticle platform for developing multifunctional tumor-targeted drug delivery vectors. Drug Development Research, 67, 47-54.
244. Hwu, J.R., Lin, Y.S., Josephrajan, T., Hsu, M.-H., Cheng, F.-Y., Yeh, C.-S., Su, W.-C., Shieh, D.-B. (2008). Targeted paclitaxel by conjugation to iron oxide and gold nanoparticles. Journal of the American Chemical Society, 131, 66-68.
245. Hawkins, M.J., Soon-Shiong, P., Desai, N. (2008). Protein nanoparticles as drug carriers in clinical medicine. Advanced Drug Delivery Reviews, 60, 876-85.
246. Henderson, I.C., Bhatia, V. (2007). Nab-paclitaxel for breast cancer: A new formulation with an improved safety profile and greater efficacy. Expert Review of Anticancer Therapy, 7, 919-943.
247. Ron, N., Cordia, J., Yang, A., Ci, S., Nguyen, P., Hughs, M., Desai, N. (2008). Comparison of physicochemical characteristics and stability of three novel formulations of paclitaxel: Abraxane, Nanoxel, and Genexol PM. Proceedings of the American Association for Cancer Research, 49, Abst. 5622.
248. Oerlemans, C., Bult, W., Bos, M., Storm, G., Nijsen, J.F.W., Hennick, W.E. (2010). Polymeric micelles in anticancer therapy: Targeting, imaging and triggered release. Pharmaceutical Research, 27, 2569-2589.
249. Aapro, M. (1996). The scientific rationale for developing taxoids. Anti-Cancer Drugs, 7, 33-36.
250. Metzger-Filho, O., Moulin, C., Azambuja, E.D., Ahamad, A. (2009). Larotaxel: Broadening the road with new taxanes. Expert Opinion on Investigational Drugs, 18, 1183-1189.