Design, synthesis, and biological evaluation of new-generation taxoids

Journal of Medicinal Chemistry

Volumn 51, Issue 11, 2008, Pages 3203-3221

  Ojima, Iwao ^a   Chen, Jin ^a   Sun, Liang ^a   Borella, Christopher P ^a   Wang, Tao ^a   Miller, Michael L ^a   Lin, Songnian ^a   Geng, Xudong ^a   Kuznetsova, Larisa ^a   Qu, Chuanxing ^a   Gallager, David ^a   Zhao, Xianrui ^a   Zanardi, Ilaria ^a   Xia, Shujun ^b   Horwitz, Susan B ^b   Mallen St Clair, Jon ^a   Guerriero, Jennifer L ^a   Bar Sagi, Dafna ^a   Veith, Jean M ^c   Pera, Paula ^c   Bernacki, Ralph J ^c   more..

^a STONY BROOK UNIVERSITY   (United States)

^b ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

^c ROSWELL PARK CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA TUBULIN; DISCODERMOLIDE; DOCETAXEL; PACLITAXEL; SB T 121303; SB T 1213031; SB T 1214; TAXOID;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER RESISTANCE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG EFFICACY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; IC 50; IN VIVO STUDY; MALE; MICROTUBULE ASSEMBLY; MOUSE; MUTATION; NONHUMAN; STRUCTURE ACTIVITY RELATION; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; BIOPOLYMERS; CELL LINE, TUMOR; DRUG DESIGN; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HUMANS; MALE; MICE; MICE, NUDE; NEOPLASM TRANSPLANTATION; PACLITAXEL; POINT MUTATION; STRUCTURE-ACTIVITY RELATIONSHIP; TAXOIDS; TRANSPLANTATION, HETEROLOGOUS; TUBULIN;

EID: 44949142967     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm800086e     Document Type: Article

References (54)

1. Jemal, A.; Ward, E.; Hao, Y.; Thun, M. Trends in the Leading Causes of Death in the United States, 1970-2002. JAMA, J. Am. Med. Assoc. 2005, 294, 1255-1259.
2. Jemal, A.; Siegel, R.; Ward, E.; Murray, T.; Xu, J.; Smigal, C.; Thun, M. J. Cancer Statistics, 2006. Ca-Cancer J. Clin. 2006, 56, 106-130.
3. Rowinsky, E. K. The Development and Clinical Utility of the Taxane Class of Antimicrotubule Chemotherapy Agents. Annu. Rev. Med. 1997, 48, 353-374.
4. Suffness, M. Taxol: Science and Applications; CRC Press: New York, 1995.
5. Schiff, P. B.; Fant, J.; Horwitz, S. B. Promotion of Microtubule Assembly in vitro by Taxol. Nature 1979, 277, 665-667.
6. Schiff, P. B.; Horwitz, S. B. Taxol Stabilizes Microtubules in Mouse Fibroblast Cells. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 1561-1565.
7. Ojima, I.; Duclos, O.; Kuduk, S. D.; Sun, C.-M.; Slater, J. C.; Lavelle, F.; Veith, J. M.; Bernacki, R. J. Synthesis and Biological Activity of 3′-Alkyl- and 3′-Alkenyl-3′-dephenyldocetaxels. Bioorg. Med. Chem. Lett. 1994, 4, 2631-2634.
8. Ojima, I.; Duclos, O.; Zucco, M.; Bissery, M.-C.; Combeau, C.; Vrignaud, P.; Riou, J. F.; Lavelle, F. Synthesis and Structure-Activity Relationships of New Antitumor Taxoids. Effects of Cyclohexyl Substitution at the C-3′ and/or C-2 of Taxotère (Docetaxel). J. Med. Chem. 1994, 37, 2602-2608.
9. Ojima, I.; Fenoglio, I.; Park, Y. H.; Pera, P.; Bernacki, R. J. Synthesis and Biological Activity of 14β-Hydroxydocetaxel. Bioorg. Med. Chem. Lett. 1994, 4, 1571-1576.
10. 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. Total Synthesis of Taxol. Nature 1994, 367, 630-634.
11. Datta, A.; Aubé, J.; Georg, G. I.; Mitscher, L. A.; Jayasinghe, L. R. The First Synthesis of a C-9 Carbonyl Modified Baccatin III Derivative and Its Conversion to Novel Taxol and Taxotère Analogues. Biomed. Chem. Lett. 1994, 4, 1831-1834.
12. Georg, G. I.; Cheruvallath, Z. S.; Himes, R. H.; Mejillano, M. R.; Burke, C. T. Synthesis of Biologically Active Taxol Analogues with Modified Phenylisoserine Side Chains. J. Med. Chem. 1992, 35, 4230-4237.
13. Georg, G. I.; Cheruvallath, Z. S.; Himes, R. H.; Mejillano, M. R. Semisynthesis and Biological Activity of Taxol Analogues: Baccatin III 13-(N-benzoyl-(2′R,3′S)-3′-(p-tolyl) isoserinate), Baccatin III 13-(N-(p-toluoyl)-(2′R, 3′S)-3′-phenylisoserinate), Baccatin III 13-(N- Benzoyl-(2′R,3′S)-3′-(p- trifluoromethylphenyl)isoserinate), and Baccatin III 13-(N-(p-trifluoromethylbenzoyl)-(2′R,3′S) -3′-phenylisoserinate). Bioorg. Med. Chem. Lett. 1992, 2, 1751-1754.
14. Ojima, I.; Wang, T.; Miller, M. L.; Lin, S.; Borella, C.; Geng, X.; Pera, P.; Bernacki, R. J. Syntheses and Structure-Activity Relationships of New Second-Generation Taxoids. Bioorg. Med. Chem. Lett. 1999, 9, 3423-3428.
15. Ojima, I.; Lin, S.; Wang, T. The Recent Advances in the Medicinal Chemistry of Taxoids with Novel β-Amino Acid Side Chains. Curr. Med. Chem. 1999, 6, 927-954.
16. Kingston, D. G. I.; Chaudhary, A. G.; Chordia, M. D.; Gharpure, M.; Gunatilaka, A. A. L.; Higgs, P. I.; Rimoldi, J. M.; Samala, L.; Jagtap, P. G.; Jiang, Y. Q.; Lin, C. M.; Hamel, E.; Long, B. H.; Fairchild, C. R.; Johnston, K. A. Synthesis and Biological Evaluation of 2-Acyl Analogues of Paclitaxel (Taxol). J. Med. Chem. 1998, 41, 3715-3726.
17. Ojima, I.; Slater, J. C.; Michaud, E.; Kuduk, S. D.; Bounaud, P.-Y.; Vrignaud, P.; Bissery, M.-C.; Veith, J.; Pera, P.; Bernacki, R. J. Syntheses and Structure-Activity Relationships of the Second Generation Antitumor Taxoids. Exceptional Activity against Drug-Resistant Cancer Cells. J. Med. Chem. 1996, 39, 3889-3896.
18. Georg, G. I.; Harriman, G. C. B.; Vander Velde, D. G.; Boge, T. C.; Cheruvallath, Z. S.; Datta, A.; Hepperle, M.; Park, H.; Himes, R. H.; Jayasinghe, L. Medicinal Chemistry of Paclitaxel: Chemistry, Structure-Activity Relationships, and Conformational Analysis. Taxane Anticancer Agents: Basic Science and Current Status; American Chemical Society: Washington, DC, 1995; pp 217-232.
19. Ojima, I.; Duclos, D.; Dormán, G.; Simonot, B.; Prestwich, G. D.; Rao, S.; Lerro, K. A.; Horwitz, S. B. A New Paclitaxel Photoaffinity Analog with a 3-(4-Benzoylphenyl)propanoyl Probe for Characterization of Drug-Binding Sites on Tubulin and P-Glycoprotein. J. Med. Chem. 1995, 38, 3891-3894.
20. Ojima, I.; Slater, J. S.; Kuduk, S. D.; Takeuchi, C. S.; Gimi, R. H.; Sun, C.-M.; Park, Y. H.; Pera, P.; Veith, J. M.; Bernacki, R. J. Syntheses and Structure-Activity Relationships of Taxoids Derived from 14β-Hydroxy-10- deacetylbaccatin III. J. Med. Chem. 1997, 40, 267-278.
21. Ojima, I.; Kuduk, S. D.; Slater, J. C.; Gimi, R. H.; Sun, C. M.; Chakravarty, S.; Ourevich, M.; Abouabdellah, A.; Bonnet-Delpon, D.; Bégué, J.-P.; Veith, J. M.; Pera, P.; Bernacki, R. J. Synthesis, Biological Activity, and Conformational Analysis of Fluorine-Containing Taxoids. Biomedical Frontiers of Fluorine Chemistry; ACS Symposium Series 639; American Chemical Society: Washington, DC, 1996; pp 228-243.
22. Ojima, I.; Zucco, M.; Duclos, O.; Kuduk, S. D.; Sun, C.-M.; Park, Y. H. N-Acyl-3-hydroxy-β-lactams as Key Intermediates for Taxotère and Its Analogs. Bioorg. Med. Chem. Lett. 1993, 3, 2479-2482.
23. Marder-Karsenti, R.; Dubois, J.; Bricard, L.; Guénard, D.; Guéritte-Voegelein, F. Synthesis and Biological Evaluation of D-Ring-Modified Taxanes: 1 5(20)-Azadocetaxel Analogs. J. Org. Chem. 1997, 62, 6631-6637.
24. Chen, S. H.; Kant, J.; Mamber, S. W.; Roth, G. P.; Wei, J.; Marshall, D.; Vyas, D.; Farina, V. Taxol Structure Activity Relationships: Synthesis and Biological Activity of Taxol and Analogs Modified at C-7. Bioorg. Med. Chem. Lett. 1994, 4, 2223-2228.
25. Ojima, I.; Sun, C. M.; Zucco, M.; Park, Y. H.; Duclos, O.; Kuduk, S. D. A Highly Efficient Route to Taxotère by the β-Lactam Synthon Method. Tetrahedron Lett. 1993, 34, 4149-4152.
26. Ojima, I.; Lin, S. Efficient Asymmetric Syntheses of β-Lactams Bearing a Cyclopropane or an Epoxide Moiety and Their Application to the Syntheses of Novel Isoserines and Taxoids. J. Org. Chem. 1998, 63, 224-225.
27. Chen, J.; Kuznetsova, L. V.; Ungreanu, I. M.; Ojima, I. Recent Advances in the Synthesis of α-Hydroxy-β-amino Acids and Their Use in the SAR Studies of Taxane Anticancer Agents. In Enantioselective Synthesis of β-Amino Acids, 2nd ed.; Juaristi, E., Soloshonok, V., Eds.; John Wiley: New York, 2005; pp 447-476.
28. Gottesman, M. M.; Fojo, T.; Bates, S. E. Multidrug Resistance in Cancer: Role of ATP-Dependent Transporters. Nat. Rev. Cancer 2002, 2, 48-58.
29. Dumontet, C.; Sikic, B. I. Mechanisms of Action of and Resistance to Antitubulin Agents: Microtubule Dynamics, Drug Transport, and Cell Death. J. Clin. Oncol. 1999, 17, 1061-1070.
30. Cabral, F.; Wible, L.; Brenner, S.; Brinkley, B. R. J. Taxol-Requiring Mutant of Chinese Hamster Ovary Cells with Impaired Mitotic Spindle Assembly. Cell Biol. 1983, 97, 30-39.
31. Schibler, M. J.; Cabral, F. Taxol-Dependent Mutants of Chinese Hamster Ovary Cells with Alterations in α- and β-Tubulin. J. Cell Biol. 1986, 102, 1522-1531.
32. Lu, Q.; Luduena, R. F. Removal of βIII Isotype Enhances Taxol Induced Microtubule Assembly. Cell Struct. Funct. 1993, 18, 173-182.
33. Haber, M.; Burkhart, C. A.; Regl, D. L.; Madafiglio, J.; Norris, M. D.; Horwitz, S. B. Altered Expression of M β2, the Class II β-TubuIin Isotype, In a Murine J774.2 Cell Line with a High Level of Taxol Resistance. J. Biol. Chem. 1995, 270, 31269-31275.
34. Giannakakou, P.; Sackett, D. L.; Kang, Y.-K.; Zhan, Z.; Buters, J. T. M.; Fojo, T.; Poruchynsky, M. S. Paclitaxel-Resistant Human Ovarian Cancer Cells Have Mutant β-Tubulins That Exhibit Impaired Paclitaxel-Driven Polymerization. J. Biol. Chem. 1997, 272, 17118-17125.
35. Kavallaris, M.; Kuo, D. Y.; Burkhart, C. A.; Regl, D. L.; Norris, M. D.; Haber, M.; Horwitz, S. B. Taxol-Resistant Epithelial Ovarian Tumors Are Associated with Altered Expression of Specific Beta-Tubulin Isotypes. J. Clin. Invest. 1997, 100, 1282-1293.
36. Ghaneh, P.; Costello, E.; Neoptolemos, J. P. Biology and Management of Pancreatic Cancer. Gut 2007, 56, 1134-1152.
37. Lage, H.; Dietel, M. Multiple Mechanisms Confer Different Drug-Resistant Phenotypes in Pancreatic Carcinoma Cells. J. Cancer Res. Clin. Oncol. 2002, 128, 349-357.
38. O'Driscoll, L.; Walsh, N.; Larkin, A.; Ballot, J.; Ooi, W. S.; Gullo, G.; O'Connor, R.; Clynes, M.; Crown, J.; Kennedy, S. MDR1/P-Glycoprotein and MRP-1 Drug Efflux Pumps in Pancreatic Carcinoma. Anticancer Res. 2007, 27, 2115-2120.
39. 2-Terminal Kinase. Cancer Res. 2006, 66, 445-452.
40. Mallen-St. Clair, J. ;Curato,J.; Chen, J.; Zhao, X. ; Chen, S.; Karpeh, M.; Ojima, I.; Bar-Sagi, D. Pre-Clinical Investigation of the Anti-Tumor Activity of Taxane Derivatives against Pancreatic Cancer. Presented at the 97th Annual Meeting of the American Association of Cancer Research, Washington, DC, April 1-5, 2006; Abstract 1963.
41. Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. Discodermolide: A New Bioactive Polyhydroxylated Lactone from the Marine Sponge Discodermia dissoluta. J. Org. Chem. 1990, 55, 4912-4915.
42. Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. Discodermolide: A New Bioactive Polyhydroxylated Lactone from the Marine Sponge Discodermia dissoluta [Erratum]. J. Org. Chem. 1991, 56, 1346.
43. ter Haar, E.; Kowalski, R. J.; Hamel, E.; Lin, C. M.; Longley, R. E.; Gunasekera, S. P.; Rosenkranz, H. S.; Day, B. W. Discodermolide, a Cytotoxic Marine Agent That Stabilizes Microtubules More Potently Than Taxol. Biochemistry 1996, 35, 243-250.
44. Klein, L. E.; Freeze, B. S.; Smith, A. B., III; Horwitz, S. B. The Microtubule Stabilizing Agent Discodermolide Is a Potent Inducer of Accelerated Cell Senescence. Cell Cycle 2005, 41, 501-507.
45. Kuznetsova, L. V.; Chen, J.; Sun, L.; Wu, X.; Pepe, A.; Veith, J. M.; Pera, P.; Bernacki, R. J.; Ojima, I. Syntheses and Evaluation of Novel Fatty Acid-2nd-Generation Taxoid Conjugates as Promising Anticancer Agents. Bioorg. Med. Chem. Lett. 2006, 16, 974-977.
46. Denis, J.-N.; Greene, A. E.; Guénard, D.; Guéritte- Voegelein, F.; Mangatal, L.; Potier, P. A. Highly Efficient, Practical Approach to Natural Taxol. J. Am. Chem. Soc. 1988, 110, 5917-5919.
47. Mangatal, L.; Adeline, M. T.; Guénard, D.; Guéritte- Voegelein, F.; Potier, P. Application of the Vicinal Oxyamination Reaction with Asymmetric Induction to the Hemisynthesis of Taxol and Analogues. Tetrahedron 1989, 45, 4177-4190.
48. Ojima, I.; Sun, C. M.; Park, Y. H. New and Efficient Coupling Method for the Synthesis of Peptides Bearing Norstatine Residue and Their Analogs. J. Org. Chem. 1994, 59, 1249-1250.
49. Ojima, I. S. L.; Inuoe, T.; Miller, M. L.; Borella, C. P.; Geng, X.; Walsh, J. J. Macrocycle Formation by Ring-Closing Metathesis (RCM). Application to the Syntheses of Novel Macrocyclic Taxoids. J. Am. Chem. Soc. 2000, 122, 5343-5353.
50. Chen, S.-H.; Farina, V.; Wei, J.-M.; Long, B.; Fairchild, C.; Mamber, S. W.; Kadow, J. F.; Vyas, D.; Doyle, T. W. Structure-Activity Relationships of Taxol: Synthesis and Biological Evaluation of C2 Taxol Analogs. Bioorg. Med. Chem. Lett. 1994, 4, 479-482.
51. Skehan, P.; Streng, R.; Scudierok, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. New Colorimetric Cytotoxicity Assay for Anticancer-Drug Screening. J. Natl. Cancer Inst. 1990, 82, 1107-1112.
52. Motulsky, H. J.; Ransnas, L. A. Fitting Curves to Data Using Nonlinear Regression: A Practical and Nonmathematical Review. FASEB J. 1987, 1, 365-374.
53. Weisenberg, R. C. Microtubule Formation in-Vitro in Solutions Containing Low Calcium Concentrations. Science 1972, 177, 1104-1105.
54. Shelanski, M. L.; Gaskin, F.; Cantor, C. R. Microtubule Assembly in the Absence of Added Nucleotides. Proc. Nat. Acad. Sci. U.S.A. 1973, 70, 765-768.