Taxoids: Cancer-fighting compounds from nature

Current Opinion in Drug Discovery and Development

Volumn 10, Issue 2, 2007, Pages 130-144

  Kingston, David G I ^a   Newman, David J ^b  

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

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

Biosynthesis; Clinical studies; Drug targeting; Medicinal chemistry; Structure activity relationship; Tubulin

Indexed keywords

2' PALMITOYLPACLITAXEL; AL 850; ANTINEOPLASTIC AGENT; AURITAX; BMS 184476; BMS 188797; BMS 275183; BRT 216; DHA SB T 1214; DJ 927; DOCETAXEL; IDN 5390; ISOTAXEL; LAROTAXEL; MILATAXEL; ORTATAXEL; PACLITAXEL; PACLITAXEL POLIGLUMEX; PNU 105298; SB RA 121012; SB RA 31012; SB T 1212; SB T 1213; SB T 12136; SBT 11033; SBT 121304; SIMOTAXEL; TAXOID; TL 310; TOCOSOL; TPI 287; TRA 2 10A; TRA 9 2A; TX 67; TXD 258; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ASPERGILLUS NIDULANS; BINDING AFFINITY; BREAST CANCER; CELL STRAIN MCF 7; CLINICAL TRIAL; DRUG ACTIVITY; DRUG BINDING; DRUG DELIVERY SYSTEM; DRUG ELUTING STENT; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; LIVER CANCER; LUNG CANCER; MALARIA; MELANOMA; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OVARY CANCER; PANCREAS CANCER; PHOTODYNAMIC THERAPY; PLASMODIUM; REVIEW; SOLID TUMOR; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; DRUG DELIVERY SYSTEMS; HUMANS; PACLITAXEL; TAXOIDS; TAXUS; TUBULIN;

EID: 33947306802     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (108)

1. Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT: Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc (1971) 93(9):2325-2327.
2. Oberlies NH, Kroll DJ: Camptothecin and taxol: Historic achievements in natural products research. J Nat Prod (2004) 67(2):129-135.
3. Cragg GM, Newman DJ: A tale of two tumor targets: Topoisomerase I and tubulin. The Wall and Wani contribution to cancer chemotherapy. J Nat Prod (2004) 67(2):232-244.
4. Zefirova ON, Nurieva EV, Ryzhov AN, Zyk NV, Zefirov NS: Taxol: Synthesis, bioactive conformations, and structure-activity relationships in its analogs. Russ J Org Chem (2005) 41(3):315-351.
5. Kingston DGI: Taxol and its analogs. In: Anticancer Agents from Natural Products. Cragg GM, Kingston DGI, Newman DJ (Eds), CRC Press, Boca Raton, FL, USA (2005):89-122.
6. Geney R, Chen J, Ojima I: Recent advances in the new generation taxane anticancer agents. Med Chem (2005) 1(2):125-139.
7. Miglarese MR, Carlson RO: Development of new cancer therapeutic agents targeting mitosis. Expert Opin Invest Drugs (2006) 15(11):1411-1425.
8. Dubois J: Recent progress in the development of docetaxel and paclitaxel analogues. Expert Opin Ther Pat (2006) 16(11):1481-1496.
9. Kingston DG: The shape of things to come: Structural and synthetic studies of taxol and related compounds. Phytochemistry (2006): Epublished ahead of print. doi:10.1016/j.phytochem.2006.11.009
10. Fang W-S, Liang X-T: Recent progress in structure activity relationship and mechanistic studies of Taxol analogues. Mini Rev Med Chem (2005) 5(1):1-12.
11. Kingston DGI, Jagtap PG, Yuan H, Samala L: The chemistry of Taxol and related taxoids. In: Progress in the Chemistry of Organic Natural Products, Volume 84. Herz W, Falk H, Kirby GW (Eds), Springer-Verlag, Vienna, Austria (2002):53-225.
12. Baloglu E, Miller ML, Cavanagh EE, Marien TP, Roller EE, Chari RV: A facile one-pot synthesis of 7-triethylsilylbaccatin III. Synlett (2005) 5:817-818.
13. Leistner E: Arzneimittel aus der natur. Die biologie der taxane [Drugs from nature. The biology of taxanes]. Pharm Unserer Zeit (2005) 34(2):98-103.
14. Jennewein S, Wildung MR, Chau M, Walker K, Croteau R: Random sequencing of an induced Taxus cell cDNA library for identification of clones involved in Taxol biosynthesis. Proc Natl Acad Sci USA (2004) 101(24):9149-9154.
15. Jennewein S, Long RM, Williams RM, Croteau R: Cytochrome P450 taxadiene 5α-hydroxylase, a mechanistically unusual monooxygenase catalyzing the first oxygenation step of Taxol biosynthesis. Chem Biol (2004) 11(3):379-387.
16. Bok JW, Hoffmeister D, Maggio-Hall LA, Murillo R, Glasner JD, Keller NP: Genomic mining for Aspergillus natural products. Chem Biol (2006) 13(1):31-37.
17. Strobel G, Daisy B, Castillo U, Harper J: Natural products from endophytic microorganisms. J Nat Prod (2004) 67(2):257-268.
18. Sankawa U, Itokawa H: Biosynthesis of taxoids. In: Taxus: The Genus Taxus. Itokawa H, Lee K-H (Eds), CRC Press, Boca Raton, FL, USA, (2003):19-34.
19. Croteau R, Ketchum RE, Long RM, Kaspera R, Wildung MR: Taxol biosynthesis and molecular genetics. Phytochemistry Rev (2006) 5(1):75-97.
20. Ojima I, Geney R, Ungureanu IM, Li D: Medicinal chemistry and chemical biology of new generation taxane antitumor agents. IUBMB Life (2002) 53(4-5):269-274.
21. Mastalerz H, Cook D, Fairchild CR, Hansel S, Johnson W, Kadow JF, Long BH, Rose WC, Tarrant J, Wu MJ, Xue MQ et al: The discovery of BMS-275183: An orally efficacious novel taxane. Bioorg Med Chem (2003) 11(20):4315-4323.
22. Study of BMS-275183 in patients with pretreated locally advanced or metastatic NSCLC (non small cell lung cancer): Clinicaltrials.gov, Bethesda, MD, USA (2007). http://clinicaltrials.gov/show/NCT00359450
23. Broker LE, de Vos FY, van Groeninger CJ, Kuenen BC, Gall HE, Woo MH, Voi MH, Gietema JA, de Vines EG, Giaccone G: Phase I trial with BMS-275183, a novel oral taxane with promising antitumor activity. Clin Cancer Res (2006) 12(6):1760-1767
24. Hwang JJ, Marshall JL, Malik S, Chun H, Ahmed T, Pilia PA: A Q7D phase I study of TPI 287, a novel taxane, in advanced malignancies: Imaging studies, pharmacokinetics (PK) and circulating tumor cell (CTC) quantitation. J Clin Oncol (2006) 24(18S):12008.
25. Sampath D, Discafani CM, Loganzo F, Beyer C, Liu H, Tan X, Musto S, Annable T, Gallagher P, Rios C, Greenberger LM: Mac-321, a novel taxane with greater efficacy than paclitaxel and docetaxel in vitro and in vivo. Mol Cancer Ther (2003) 2(9):873-884.
26. Sampath D, Greenberger LM, Beyer C, Hari M, Liu H, Baxter M, Yang S, Rios C, Discafani C: Preclinical pharmacologic evaluation of MST-997, an orally active taxane with superior in vitro and in vivo efficacy in paclitaxel- and docetaxel-resistant tumor models. Clin Cancer Res (2006) 12(11 Pt 1):3459-3469.
27. Longley RE, Fasciani G, Sander L, Holton R: In vitro mechanism of action studies with the taxane analog, TL-310. 96th Annual American Association for Cancer Reearch Meeting, Anaheim, CA, USA (2005): LB-280.
28. Baldelli E, Battaglia A, Bombardelli E, Carenzi G, Fontana G, Gelmi ML, Guerrini A, Pocar D: New taxane derivatives: Synthesis of baccatin[14,1-d]furan-2-one nucleus and its condensation with the norstatine side chain. J Org Chem (2004) 69(20):6610-6616.
29. Rice A, Liu Y, Michaelis ML, Himes RH, Georg GI, Audus KL: Chemical modification of paclitaxel (Taxol) reduces P-glycoprotein interactions and increases permeation across the blood-brain barrier in vitro and in situ. J Med Chem (2005) 48(3):832-838.
30. Kobayashi J, Hosoyama H, Wang X-X, Shigemori H, Sudo Y, Tsuruo T: Modulation of multidrug resistance by taxuspine C and other taxoids from Japanese yew. Bioorg Med Chem Lett (1998) 8(12):1555-1558.
31. Hosoyama H, Shigemori H, Tomida A, Tsuruo T, Kobayashi J: Modulation of multidrug resistance in tumor cells by taxinine derivatives. Bioorg Med Chem Lett (1999) 9(3):389-394.
32. Kobayashi J, Hosoyama H, Wang X-X, Shigemori H, Koiso Y, Iwasaki S, Sasaki T, Naito M, Tsuruo T: Effects of taxoids from Taxus cuspidata on microtubule depolymerization and vincristine accumulation in MDR cells. Bioorg Med Chem Lett (1997) 7(4):393-398.
33. Ojima I, Borella CP, Wu X, Bounaud PY, Oderda CF, Sturm M, Miller ML, Chakravarty S, Chen J, Huang Q, Pera P et al: Design, synthesis and structure - activity relationships of novel taxane-based multidrug resistance reversal agents. J Med Chem (2005) 48(6):2218-2228. • First comprehensive evaluation of the significance of taxane-based MDR agents.
34. Tarrant JG, Cook D, Fairchild C, Kadow JF, Long BH, Rose WC, Vyas D: Synthesis and biological activity of macrocyclic taxane analogues. Bioorg Med Chem Lett (2004) 14(10):2555-2558.
35. Jordan MA, Wilson L: Microtubules as a target for anticancer drugs. Nature Rev Cancer (2004) 4(4):253-265. • Good overview of the microtubule-paclitaxel interaction.
36. Schiff PB, Fant J, Horwitz SB: Promotion of microtubule assembly in vitro by Taxol. Nature (1979) 277(5698):665- 667.
37. Xiao H, Verdier-Pinard P, Fernandez-Fuentes N, Burd B, Angeletti R, Fiser A, Horwitz SB, Orr GA: Insights into the mechanism of microtubule stabilization by Taxol. Proc Natl Acad Sci USA (2006) 103(27):10166-10173.
38. Rao S, Krauss NE, Heerding JM, Swindell CS, Ringel I, Orr GA, Horwitz SB: 3′-(p-Azidobenzamido)Taxol photolabels the N-terminal 31 amino acids of β-tubulin. J Biol Chem (1994) 269(5):3132-3134.
39. Rao S, Orr GA, Chaudhary AG, Kingston DG, Horwitz SB: Characterization of the taxol binding site on the microtubule. J Biol Chem (1995) 270(35):20235-20238.
40. Lowe J, Li H, Downing KH, Nogales E: Refined structure of αβ-tubulin at 3.5 Å resolution. J Mol Biol (2001) 313(5):1045-1057. •• Foundational results for all research on the structure of tubulin and the paclitaxel-tubulin interaction.
41. Dubois J, Guenard D, Gueritte-Voeglein F, Guedira N, Potier P, Gillet B, Betoeil J-C: Conformation of taxotere and analogues determined by NMR spectroscopy and molecular modeling studies. Tetrahedron (1993) 49(30):6533-6544.
42. Williams HJ, Scott AI, Dieden RA, Swindell CS, Chirlian LE, Francl MM, Heerding JM, Krauss NE: NMR and molecular modeling study of active and inactive taxol analogues in aqueous and nonaqueous solution. Can J Chem (1994) 72(1):252-260.
43. Vander Velde DG, Georg GI, Grunewald GL, Gunn CW, Mitscher LA: "Hydrophobic collapse" of Taxol and taxotere solution conformations in mixtures of water and organic solvent. J Am Chem Soc (1993) 115(24):11650-11651.
44. Gomez Paloma L, Guy RK, Wrasidlo W, Nicolaou KC: Conformation of a water-soluble derivative of taxol in water by 2D-NMR spectroscopy. Chem Biol (1994) 1(2):107-112.
45. Ojima I, Chakravarty S, Inoue T, Lin S, He L, Horwitz SB, Kuduk SC, Danishefsky SJ: A common pharmacophore for cytotoxic natural products that stabilize microtubules. Proc Natl Acad Sci USA (1999) 96(8):4256-4261.
46. Snyder JP, Nettles JH, Cornett B, Downing KH, Nogales E: The binding conformation of Taxol in β tubulin: A model based on the electron crystallographic density. Proc Natl Acad Sci USA (2001) 98(9):5312-5316. •• First proposal of the T-taxol conformation as the tubulin-binding conformation of paclitaxel.
47. Geney R, Sun L, Pera P, Bernacki RJ, Xia S, Horwitz SB, Simmerling CL, Ojima I: Use of the tubulin bound paclitaxel conformation for structure-based rational drug design. Chem Biol (2005) 12(3):339-348.
48. Li Y, Poliks B, Cegelski L, Poliks M, Gryczynski Z, Piszczek G, Jagtap PG, Studelska DR, Kingston DG, Schaefer J, Bane S: Conformation of microtubule-bound paclitaxel determined by fluorescence spectroscopy and REDOR NMR. Biochemistry (2000) 39(2):281-291. • First application of REDOR NMR to the elucidation of the tubulin-binding conformation of paclitaxel.
49. Paik Y, Yang C, Metaferia B, Tang S, Bane S, Ravindra R, Shanker N, Alcaraz AA, Johnson SA, Schaefer J, O'Connor RD et al: Rotational-echo double-resonance NMR distance measurements for the tubulin-bound paclitaxel conformation. J Am Chem Soc (2006) 129(2):361-370. •• Detailed analysis of REDOR NMR and molecular modeling data demonstrating that the T-taxol conformation is the best model of the tubulinbinding conformation of paclitaxel.
50. Johnson SA, Alcaraz AA, Snyder JP: T-taxol and the electron crystallographic density in β-tubulin. Org Lett (2005) 7(25):5549-5552.
51. Kingston DG, Bane S, Snyder JP: The Taxol pharmacophore and the T-taxol bridging principle. Cell Cycle (2005) 4(2):279-289.
52. Querolle O, Dubois J, Thoret S, Roussi F, Guéritte F, Guénard D: Synthesis of C2-C3′N-linked macrocyclic taxoids. Novel docetaxel analogues with high tubulin activity. J Med Chem (2004) 47(24):5937-5944.
53. Larroque A-L, Dubois J, Thoret S, Aubert G, Chiaroni A, Gueritte F, Guenard D: Novel C2-C3′ N-peptide linked macrocyclic taxoids. Part 2: Synthesis and biological activities of docetaxel analogues with a peptide side chain at C2 and their macrocyclic derivatives. Bioorg Med Chem (2007) 15(1):563-574.
54. Ganesh T, Guza RC, Bane S, Ravindra R, Shanker N, Lakdawala AS, Snyder JP, Kingston DG: The bioactive Taxol conformation on β-tubulin: Experimental evidence from highly active constrained analogs. Proc Natl Acad Sci USA (2004) 101(27):10006-10011. •• First synthesis of bridged paclitaxels that adopt the T-taxol conformation and have improved cytotoxicity and tubulin-assembly activity compared to paclitaxel.
55. Ganesh T, Yang C, Norris A, Glass T, Bane S, Ravindra R, Banerjee A, Metaferia B, Thomas SL, Giannakakou P, Alcaraz AA et al: Evaluation of the tubulin-bound paclitaxel conformation: Synthesis, biology and SAR studies of C4 to C3′ bridged paclitaxel analogs. J Med Chem (2007) 50(4):713-725.
56. Tang S, Yang C, Brodie P, Bane S, Ravindra R, Sharma S, Jiang Y, Snyder JP, Kingston DG: Bridging converts a noncytotoxic nor- paclitaxel derivative to a cytotoxic analogue by constraining it to the T-taxol conformation. Org Lett (2006) 8(18):3983-3986.
57. Ganesh T, Norris A, Sharma S, Bane S, Alcaraz AA, Snyder JP, Kingston DG: Design, synthesis, and bioactivity of simplified paclitaxel analogs based on the T-taxol bioactive conformation. Bioorg Med Chem (2006) 14(10):3447-3454.
58. Gradishar WJ: Albumin-bound paclitaxel: A next-generation taxane. Expert Opin Pharmacother (2006) 7(8):1041-1053. • Review of the first new paclitaxel formulation to be approved by the FDA.
59. Green MR, Manikhas GM, Orlov S, Afanasyev B, Makhson AM, Bhar P, Hawkins MJ: Abraxane, a novel cremophor-free, albumin-bound particle form of paclitaxel for the treatment of advanced non-small-cell lung cancer. Ann Oncol (2006) 17(8):1263-1268.
60. Schacter LP, Bukowski RM, Carducci MA, Donehower R, Dunlop D, Evans TR, Gilby E, Johnston S: Safety profile of DHA-paclitaxel (TXP) in 8 phase II trials. Proc Am Soc Clin Oncol (2003):Abs 856.
61. Kuznetsova L, Chen J, Sun L, Wu X, Pepe A, Veith JM, Pera P, Bernacki RJ, Ojima I: Syntheses and evaluation of novel fatty acid-second-generation taxoid conjugates as promising anticancer agents. Bioorg Med Chem Lett (2006) 16(4):974-977.
62. Singer JW, Shaffer S, Baker B, Bernareggi A, Stromatt S, Nienstedt D, Besman M: Paclitaxel poliglumex (XYOTAX; CT-2103): An intracellularly targeted taxane. Anticancer Drugs (2005) 16(3):243-254.
63. Langer CJ, Socinski MA, Ross H, O'Byrne KJ: Paclitaxel poliglumex (PPX)/carboplatin vs paclitaxel/carboplatin for the treatment of PS2 patients with chemotherapy-naïve advanced non-small cell lung cancer (NSCLC): A phase III study. J Clin Oncol (2005):23(16S):LBA7011.
64. Liang H-F, Chen S-C, Chen M-C, Lee P-W, Chen C-T, Sung H-W: Paclitaxel-loaded poly(γ-glutamic acid)-poly(lactide) nanoparticles as a targeted drug delivery system against cultured HEPG2 cells. Bioconjug Chem (2006) 17(2):291-299.
65. Zakharian TY, Seryshev A, Sitharaman B, Gilbert BE, Knight V, Wilson LJ: A fullerene-paclitaxel chemotherapeutic: Synthesis, characterization, and study of biological activity in tissue culture. J Am Chem Soc (2005) 127(36):12508-12509. • First example of a fullerene-linked paclitaxel.
66. Paciotti GF, Myer L, Kingston DG, Ganesh T, Tamarkin L: Colloidal gold nanoparticles: A versatile platform for developing tumor targeted cancer therapies. In: Nanotech 2005 Vol. 1 Technical Proceedings of the 2005 NSTI Nanotechnology Conference and Trade Show, Volume 1 (2005):7-10.
67. El Alaoui A, Saha N, Schmidt F, Monneret C, Florent J-C: New Taxol (paclitaxel) prodrugs designed for ADEPT and PMT strategies in cancer chemotherapy. Bioorg Med Chem (2006) 14(14):5012-5019.
68. de Groot FM, van Berkom LW, Scheeren HW: Synthesis and biological evaluation of 2′-carbamate-linked and 2′-carbonate-linked prodrugs of paclitaxel: Selective activation by the tumor-associated protease plasmin. J Med Chem (2000) 43(16):3093-3102.
69. Damen EW, Nevalainen TJ, van den Bergh TJ, de Groot FM, Scheeren HW: Synthesis of novel paclitaxel prodrugs designed for bioreductive activation in hypoxic tumour tissue. Bioorg Med Chem (2002) 10(1):71-77.
70. Guillemard V, Saragovi HU: Taxane-antibody conjugates afford potent cytotoxicity, enhanced solubility, and tumor target selectivity. Cancer Res (2001) 61(2):694-699.
71. Miller ML, Roller EE, Wu X, Leece BA, Goldmacher VS, Chari RV, Ojima I: Synthesis of potent taxoids for tumor-specific delivery using monoclonal antibodies. Bioorg Med Chem Lett (2004) 14(15):4079-4082.
72. Skwarczynski M, Noguchi M, Hirota S, Sohma Y, Kimura T, Hayashi Y, Kiso Y: Development of first photoresponsive prodrug of paclitaxel. Bioorg Med Chem Lett (2006) 16(17):4492-4496. • An interesting new approach to converting a prodrug into paclitaxel.
73. Sinou V, Grellier P, Schrevel J: In vitro and in vivo inhibition of erythrocytic development of malarial parasites by docetaxel. Antimicrob Agents Chemother (1996) 40(2):358-361.
74. Seitz HM, Gottwald F, Proft J, Wingen F, Maier W: Docetaxel (taxotere): Effectiveness against Plasmodium falciparum in vitro and Plasmodium yoelii nigeriensis in vivo. Tokai J Exp Clin Med (1998) 23(6):427-430.
75. Chen J, Kuznetsova L, Sun L, Zhao X, Wu X, Huang Q, Chibale K, Clarkson C, Smith P, Croft SL, Ojima I: Design, synthesis, and evaluation of taxanes as potential antimalarial agents. 226th American Chemical Society National Meeting, New York, NY, USA (2003):MEDI 259.
76. Huang Q, Kirikae F, Kirikae T, Pepe A, Amin A, Respicio L, Slayden RA, Tonge PJ, Ojima I: Targeting FtsZ for antituberculosis drug discovery: Noncytotoxic taxanes as novel antituberculosis agents. J Med Chem (2006) 49(2):463-466.
77. Li G, Faibushevich A, Turunen BJ, Yoon SO, Georg G, Michaelis ML, Dobrowsky RT: Stabilization of the cyclin-dependent kinase 5 activator, p35, by paclitaxel decreases β-amyloid toxicity in cortical neurons. J Neurochem (2003) 84(2):347-362.
78. Ojima I, Geng X, Wu X, Qu C, Borella CP, Xie H, Wilhelm SD, Leece BA, Bartle LM, Goldmacher VS, Chari RV: Tumor-specific novel taxoid-monoclonal antibody conjugates. J Med Chem (2002) 45(26):5620-5623.
79. Bergstralh DT, Ting JP: Microtubule stabilizing agents: Their molecular signaling consequences and the potential for enhancement by drug combination. Cancer Treat Rev (2006) 32(3):166-179. • Contains a good discussion of the various currently recognized signal transduction pathways that may be influenced by tubulin stabilizers and indicates the current state of experimentation (preclinical through to phase II clinical testing).
80. Hennenfent KL, Govindan R: Novel formulations of taxanes: A review. Old wine in a new bottle? Ann Oncol (2006) 17(5):735-749. • Excellent discussion of the various formulation techniques that have been tried and suggested in efforts to increase the solubility of taxane-based agents and reduce the pharmacological effects of the solubilizing agents.
81. Mahindroo N, Liou J-P, Chang J-Y, Hsieh H-P: Antitubulin agents for the treatment of cancer - a medicinal chemistry update. Expert Opin Ther Pat (2006) 16(5):647-691. • A thorough study of antitubulin agents reported in the recent patent literature, contrasting all classes of agents whether tubulin stabilizers or destabilizers, and demonstrating parenthetically the diversity of nature as a source of active skeletons.
82. Herdeg C, Oberhoff M, Karsch KR: Antiproliferative stent coatings: Taxol and related compounds. Semin Intervent Cardiol (1998) 3(3-4):197-199.
83. Halkin A, Stone, GW: Polymer-based paclitaxel-eluting stents in percutaneous coronary intervention: A review of the TAXUS trials. J Intervent Cardiol (2004) 17(5):271-282.
84. Dieras V, Valero V, Limentani S, Romieu G, Tubiana-Hulin M, Lortholary A, Ferrero J-M, Kaufman P, Buchbinder A, Besenval M: Multicenter, non-randomized phase II study with RPR109881 in taxane-exposed metastatic breast cancer (MBC) patients (PTS): Final results. Proc Am Soc Clin Oncol (2005) 23(16S):Abs 565.
85. Lissianskaya A, Gershanovich M, Ognerubov N, Golubeva O, Pratt J: Paclitaxel injectable emulsion: Phase 2a study of weekly administration in patients with platinum-resistant ovarian cancer. Proc Am Soc Clin Oncol (2004) 22(14S):Abs 5047.
86. Baumann K: Jenseits von Paclitaxel und Docetaxel. Neue Mikrotubuli-Stabilisatoren [New microtubule stabilizers]. Pharm Unserer Zeit (2005) 34(2):110-114.
87. Camps C, Felip E, Sanchez JM, Massuti B, Artal A, Paz-Ares L, Carrato A, Alberola V, Blasco A, Baselga J, Astier L et al: Phase II trial of the novel taxane BMS-184476 as second-line in non-small-cell lung cancer. Ann Oncol (2005) 16(4):597-601.
88. du Bois A, Jung B, Loehr A, Schaller-Kranz T, Cohen M, Frickhofen N: A phase I and pharmacokinetic study of novel taxane BMS-188797 and cisplatin in patients with advanced solid tumours. Br J Cancer (2006) 94(1):79-84.
89. 2, well below the normal clinical dose of paclitaxel.
90. Bourbouloux E, Campone M, Vermorken JB, Martin M, Sessa C, Perotti A: Phase I study of intravenous (iv) milataxel in adult patients with advanced malignant tumors. Proc Am Soc Clin Oncol (2006):Abs 2037.
91. Papyan A, Werner A, Ischenko I, Yezhelyev M, Teifel M, Michaelis Y, Bruns CJ: MBT-0206 enhances the anti-tumor treatment in a highly metastatic human pancreatic cancer mouse model. Proc Am Assoc Cancer Res (2004):Abs 4104.
92. Damjanov N, Fishman MN, Steinberg JL, Fetterly GJ, Haas A, Grahn A, Lauay C, Dul JL, Sherman JW, Rubin EH: Final results of a phase I study of liposome entrapped paclitaxel (LEP-ETU) in patients with advanced cancer. Proc Am Soc Clin Oncol (2005):Abs 2048.
93. Tan AR, Hanauske AR, Gelderblom H, Scheulen ME, Van Warmerdam LJ, Rosing H, Fetterly GJ, Shu VS, Sherman JW, Rubin EH: Results of a clinical pharmacokinetic (PK) bioequivalence (BE) study of liposomal paclitaxel (LEP-ETU) versus paclitaxel (T) in patients with advanced cancer. J Clin Oncol (2006) 24(18S):Abs 2017.
94. Olszanski AJ, Lewis LD, Mita C, Walovitch RC, Perez RP, Tuck DP, Rowinsky EK: Phase I and pharmacokinetic study of AI-850, a novel microparticle hydrophobic drug delivery system (HDDS) for paclitaxel. Proc Am Soc Clin Oncol (2004):Abs 2048.
95. Straub JA, Chickering DE, Lovely JC, Zhang H, Shah B, Waud WR, Bernstein H: Intravenous hydrophobic drug delivery: A porous particle formulation of paclitaxel (AI-850). Pharm Res (2005) 22(3):347-355.
96. Lockhart AC, Hochster H, Wang K, Paty V, Grover J, Leister C, Shapiro M, Rothenberg ML, Bukowski RM: Intravenous MST-997 (TL-909) formulated in intralipid 20% administered weekly in subjects with advanced malignant solid tumors: A phase I dose-escalation study. Proc Am Soc Clin Oncol (2005):Abs 2106.
97. Hwang, JJ, Marshall, JL, Malik, S, Chun, H, Ahmed, T, Pilia, PA. A Q7D phase I study of TPI 287, a novel taxane, in advanced malignancies: Imaging studies, pharmacokinetics (PK) and circulating tumor cell (CTC) quantitation. J Clin Oncol (2006) 24(18S):Abs 12008.
98. Longley RE, Clement C, Metts L, Holton RA: In vivo efficacy of TL-310: A new, orally active taxane analog. Proc Am Assoc Cancer Res (2006):Abs A7363.
99. Ojima I, Duclos O, Kuduk SD, Sun C-M, Slater JC, Lavelle F, Veith JM, Bernacki RJ: Synthesis and biological activity of 3′-alkyl- and 3′-alkenyl-3′dephenyldocetaxels. Bioorg Med Chem Lett (1994) 4(21):2631-2634.
100. Ali S, Ahmad I, Peters A, Masters G, Minchey S, Janoff A, Mayhew E: Hydrolyzable hydrophobic taxanes: Synthesis and anti-cancer activities. Anticancer Drugs (2001) 12(2):117-128.
101. Jordan MA, Ojima I, Rosas F, Distefano M, Wilson L, Scambia G, Ferlini C: Effects of novel taxanes SB-T-1213 and IDN5109 on tubulin polymerization and mitosis. Chem Biol (2002) 9(1):93-101.
102. Giribone, D, Fontana, E. Synthesis of the taxane analogue PNU-105298 labelled with deuterium and with carbon-14. J Labelled Compd Radiopharm (2000) 43(9):933-941.
103. Brooks T, Minderman H, O'Loughlin KL, Pera P, Ojima I, Baer MR, Bernacki RJ: Taxane-based reversal agents modulate drug resistance mediated by P-glycoprotein, multidrug resistance protein, and breast cancer resistance protein. Mol Cancer Ther (2003) 2(11):1195-1205.
104. Taraboletti G, Micheletti G, Giavazzi R, Riva A: IDN 5390: A new concept in taxane development. Anticancer Drugs (2003) 14(4):255-258.
105. Wu X, Ojima I: Tumor specific novel taxoid-monoclonal antibody conjugates. Curr Med Chem (2004) 11(4):429-438. • Review of the Ojima approach to the synthesis of paclitaxel-antibody conjugates, in which excellent activities for some conjugates are reported.
106. Wrasidlo W, Gaedicke G, Guy RK, Renaud J, Pitsinos E, Nicolaou K, Reisfeld RA, Lode HN: A novel 2′-(N-methylpyridinium acetate) prodrug of paclitaxel induces superior antitumor responses in preclinical cancer models. Bioconjug Chem (2002) 13(5):1093- 1099.
107. Hayashi Y, Skwarczynski M, Hamada Y, Sohma Y, Kimura T, Kiso Y: A novel approach of water-soluble paclitaxel prodrug with no auxiliary and no byproduct: Design and synthesis of isotaxel. J Med Chem (2003) 46(18):3782-3784.
108. CIPLA LTD (Rao DR, Kankan RN): Process for preparing paclitaxel. WO-2004007473 (2004).