Comparative molecular field analysis of a series of paclitaxel analogues

Journal of Medicinal Chemistry

Volumn 40, Issue 26, 1997, Pages 4319-4328

  Zhu, Qiqing ^a   Guo, Zongru ^a   Huang, Niu ^a   Wang, Minmin ^a   Chu, Fengming ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

DOCETAXEL; PACLITAXEL; PACLITAXEL DERIVATIVE; TAXOID; TUBULIN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG CONFORMATION; ELECTRIC FIELD; MICROTUBULE ASSEMBLY; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; CRYSTALLOGRAPHY, X-RAY; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PACLITAXEL; POLYCYCLIC COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0031463596     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970442u     Document Type: Article

References (55)

1. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. 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, 2325-2327.
2. For review: Rowinsky, E. K.; Donehower, R. C. The Clinical Pharmacology and Use of Antimicrotubule Agents in Cancer Chemotherapeutics. Pharmacol. Ther. 1991, 52, 35-84.
3. For review: Rowinsky, E. K.; Donehower, R. C. Taxol: Twenty Years Later, The Story Unfolds. J. Natl. Cancer Inst. 1991, 83, 1778-1781.
4. For several review on clinical topics, see: Paclitaxel (Taxol) Investigator's Workshop. Proceedings of a Johns Hopkins Oncology Center Workshop. Semin. Oncol. Suppl. 3 1993, 20, 1-60.
5. Suffness, M. Taxol: From Discovery to Therapeutic Use. In Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed.; Academic Press: San Diego, 1993; Vol. 28, Chapter 32, pp 305-314.
6. Gueritte-Voegelein, F.; Le Goff, M. T.; Mangatal, L.; Potier, P. Relationship between the Structure of Taxol Analogues and Their Antimitotic Activity. J. Med. Chem. 1991, 34, 992-998.
7. Mangeney, P.; Andriamiamialisoa, Z.; Lallemand, Y.; Laanglois, Y.; Langlois, N.; Potier, P. 5′-NOR Anhydrovinblastine Prototypy of A New Class of Vinblastine Derivatives. Tetrahedron 1979, 35, 2175-2174.
8. Schiff, P. B.; Fant, J.; Horwitz, S. B. Promotion of Microtubule Assembly in vitro by Taxol. Nature 1979, 277, 665-666.
9. Rowinsky, E. K.; Onetto, N.; Canetta, R. M.; Arbuck, S. G. Taxol: The First of the Taxanes, and Important New Class of Antitumor Agents. Seminars OncoL 1992, 19, 646-662.
10. Seidman, A. D. Clinical Results of Taxol in Treatment of Advanced Breast Cancer: Single Agent Trials. Stony Brook Symposium on taxol and taxotere, May 14-15, 1993, Stony Brook, NY, Abstracts pp 14-16.
11. Horwitz, S. B. Taxol: Mechanism of Action and resistance, Stony Brook Symposium on Taxol and Taxotere, May 14-15, 1993, Stony Brook, NY, Abstracts pp 23-24.
12. Denis, J. S.; Greene, A. E.; Guenard, D.; Gueritte-Voegelein, F.; Mangatal, L.; Potier, P. A Highly Efficient, Practical Approach to Natural Taxol. J. Am. Chem. Soc. 1988, 110, 5917-5919.
13. For review: Georg, G. I.; Ali, S. M.; Zygmunt, J.; Jayasinghe, L. R. Taxol: A Novel Antitumor Agent. Exp. Opin. Ther. Pat. 1994, 4, 109-120.
14. For review: Nicolaou, K. c.; Dai, W.-M.; Guy, R. K. Chemitry and Biology of Taxol. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44.
15. Taxane Anticance agents: Basic Science and Current Status; Georg, G. I., Chen, T. T., Ojima, I., Vyas, D. M., Ed.; American Chemical Society: Washington, DC, 1995.
16. Kant, J.; Huuang, S.; Wong, H.; Fairchild, C.; Vyas, D.; Farina, V. Studies toward Structure-Activity Relationships of Taxol;Synthesis and Cytotoxicity of Taxol Analogues with C-2′Modified Phenylisoserine Side Chain. Bioorg. Med. Chem. Lett. 1993, 3, 2471-2474.
17. Swindell, C. S.; Krauss, N. E.; Horwitz, S. B.; Ringgel, L. Biologically Active Taxol Analogues with Deleted A-Ring Side Chain Substituents and Variable C-2′Configurations. J. Med. Chem. 1991, 34, 1176-1184.
18. Kington, D. G. I.; Molinero, A. A.; Rimoldi, J. M. The Taxane Diterpenoids. In Progress in the Chemistry of Organic Natural Products; Springer: New York, 1993; pp 1-206.
19. Cramer, R. D., III; Patterson, D. E.; Bunce, J. D. Comparative Molecular Field Analysis (CoMFA). 1. Effect of Shape on Binding of Steroids to Carrier Proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
20. Lataste, H.; Senilh, V.; Wright, M.; Guenard, D.; Potier, P. Relationships between the Structures of Taxol and Baccatine III Derivatives and Their in vitro Action on the Disassembly of Mammalian Brain and Physarum Amoebal Microtubules. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 4090-4094.
21. Dubois, J.; Guenard, D.; Gueritte-Voegelein, F.; Guedira, N.; Potier, P.; Gillet, B.; Beloeil, J. C. Conformation of Taxotere and Analogues Determined by NMR Spectroscopy and Molecular Modeling Studies. Tetrahedron 1993, 49, 6533-6544.
22. For review: Hepperle, M.; Georg, G. I. Taxol Analogs. Drugs Future 1994, 19, 573-584.
23. Ali, S. M.; Hoemann, M. Z.; Aube, J.; Georg, G. I.; Mitscher, L. A. Butitaxel Analogue: Synthesis and Structure-Activity Relationships. J. Med. Chem. 1997, 40, 236-241.
24. Ojima, L; 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′-Alky]- and 3′-Alkenyl-3′-Dephenyldocetaxels. Bioorg. Med. Chem. Lett. 1994, 4, 2631-2634.
25. Li, 1.; Thomas, S. A.; Klein, L. L.; Yeung, C. M.; Maring, C. J.; Grampovnik, D. J.; Lartey, P. A.; Plattner, J. J. Synthesis and Biological Evaluation of C-3&-Modified Analogs of 9(R)-Dihydrotaxol. J. Med. Chem. 1994, 37, 2655-2663.
26. Maring, C. J.; Grampovnik, D. J.; Yeung, C. M.; Klein, L. L.; Li, L.; Thomas, S. A.; Plattner, J. J. C-3′-N-Acyl Analogs of 9(R)-Dihydrotaxol: Synthesis and Structure-Activity Relationships. Bioorg. Med. Chem. Lett. 1994, 4, 1429-1432.
27. Chen, S. H.; Wei, J. W.; Long, B. H.; Fairchild, C. A.; Carboni, J.; Mamber, S. W.; Rose, W. C.; Johnston, K.; Casazza, A. M.; Kadow, J. F.; Farina, V.; Vyas, D. M.; Doyle, T. W. Novel C-4 Paclitaxel (Taxol) Analogs: Potent Antitumor Agents. Bioorg. Med. Chem. Lett. 1995, 5, 2741-2746.
28. Ojima, I.; Duclos, O.; Zucco, M.; Bissery, M. C.; Combeau, C.; Vrignard, P.; Riou, J. F.; and Lavelle, F. Synthesis and Structure-Activity Relationships of New Antitumor Taxoids: Effects of Cyclohexyl Substitution at the C-3′and/or C-2 of Taxotere (Docetaxel). J. Med. Chem. 1994, 37, 2602-2608.
29. Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; and Georg, G. I. The Effect of the Aromatic Rings of Taxol on Biological Activity and Solution Conformation: Synthesis and Evaluation of Saturated Taxol and Taxotere. J. Med, Chem. 1994, 37, 3337-3343.
30. Klein, L. L.; Li, L.; Maring, C. J.; Yeung, C. M.; Thomas, S. A.; Grampovnik, D. J.; Plattner, J. J. Antitumor Activity of 9(R)-Dihydrotaxane Analogs. J. Med. Chem. 1995, 38, 1482-1492.
31. Ojima I.; Fenoglio I.; Park, Y. H.; Pera, P.; Bernacki, R. J. Synthesis and Biological Activity of 14-Hydroxydocetaxel. Bioorg. Med. Chem. Lett. 1994, 4, 1571-1576.
32. Harriman G. C. B.; Jalluri, R. K.; Grunewald, G. L.; Vander Velde, D. G.; Georg, G. I. The Chemistry of the Taxane Diterpene: Stereoselective Syntheis of 10-Deacetoxy-ll,12-epoxypaclitaxel. Tetrahedron Lett. 1995, 36, 8909-8912.
33. 13C-NMR Assignments for Taxol, 7-epi-taxol, and Cephalomannine. J. Nat. Prod. 1992, 55, 414-423.
34. (b) Baker, J. K. Nuclear Overhauser Effect Sspectroscopy (NOESY) and Dihedral Angle Measurements in the Determination of the Conformation of Taxol in Solution. Spectrosc. Lett. 1992, 25, 31-48.
35. (c) Falzone, C. J.; Lecomte, J. T. J. Characterization of Taxol in Methylene Chloride by NMR Spectroscopy. Tetrahedron Lett. 1992, 33, 1169-1172.
36. (d) Hilton, B. D.; Chmurny, G. N.; Musckik, G. M. Taxol: Quantitative Inter-nuclear Proton-Proton Distance in Deuterated Chloroform Solution from NOE Data: 2D NMR ROESY Buildup Rates at 500 Mhz. J. Nat. Prod. 1992, 55, 1157-1161.
37. (e) Williams, H. J.; Scott, A. I.; Dieden, R. A.; Swindell, C. S.; Chirlian, L. E.; Franel, M. M.; Heerding, J. M.; Krause, N. E. NMR and Molecule Modeling Study of the Conformation of Taxol and of Its Side Chain Methyl Ester in Aqueous and non-Aqueous Solution. Tetrahedron 1993, 49, 6545-6560.
38. (f) Cachau, R. E.; Gussio, R.; Beutler, J. W. Solution Structure of Taxol Determinated Using a Novel Feedback-Scaling Procedure for NOE-Restrained Molecular Dynamics. Supercomput. Appl. High Perform. Comput. 1994, 8, 24-34.
39. (g) Balasubramanian, S. V.; Straubinger, R. M. Taxol-lipid Intercations: Taxol-Dependent Effects on the Physical Properties of Model Membranes. Biochemistry 1994, 33, 8941-8947.
40. Gueritte-Voegelein, F.; Guenard, D.; Mangatal, L.; Potier, P.; Guilhem, J.; Cesario, M.; Rascard, C. Structure of a Synthetic Taxol Precursor: N-tert-butoxycarbonyl-10-deacetyl-N-debenzoyl-Taxol. Acta Crystallogr. 1990, C46, 781-784.
41. (b) Gao, Q.; Wei, J. M.; Chen, S. H. Crystal Structure of 2-Debenzoyl, 2-Acetoxy Paclitaxel (taxol): Conformation of the Paclitaxel Side-Chain. Pharm. Res. 1995, 12, 337-341.
42. (c) Gao, Q.; Golik, J. 2′-Carbamate taxol. Acta Crystallogr. 1995, C51, 295-298.
43. (d) Mastropaolo, D.; Camerman, A.; Luo, Y.; Brayer, G. D.; Camerman, N. Crystal and Molecular Structure of Paclitaxel (taxol). Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6920-6924.
44. The program SYBYL 6.0/6.04 is available from Tripos Assoc., 1699 S Hanley Rd, St. Louis, MO 63144.
45. Clark, M.; Cramer, R. D., III; Van Opdenbosh, N. Validation Of the General purpose Tripos 5.2 Force Field. J. Comput. Chem. 1989, 10, 982-1012.
46. Powell, M. J. D. Restart Procedure for the Conjugate Gradient Method. Math. Program 1977, 12, 214.
47. Wold, S.; Albano, C.; Dunn, W. J., III; Edlund, U.; Esbensen, K.; Geladi, P.; Hellberg, S.; Johansson, E.; Lindberg, W.; Sjiostrom, M. Multivariate Data Analysis in Chemistry. In CHEMOMETRICS: Mathematics and Statistics in Chemistry; Kowalski, B., Ed.; Reidel: Dordrecht, The Netherlands, 1984.
48. (b) Sybyl Molecular Modeling Software, version 6.02, 1993. Tripos Associates, Inc., St. Louis, MO 63144; Sybyl theory manual, 1993.
49. (b) Sybyl Molecular Modeling Software, version 6.02, 1993. Tripos Associates, Inc., St. Louis, MO 63144; Sybyl theory manual, 1993.
50. Cramer, R. D., III; Bunce, J. D.; Patterson, D. E.; Frank, I. E. Crossvalidation, Bootstrapping, and Partial Leat Squares Compared with Multiple Regression in Conventional QSAR Studies. Quant. Struct.-Act. Relat. 1988, 7, 18-25.
51. Klebe, G.; Abraham, U. On the Prediction of Binding Properties of Drug Molecules by Comparative Molecular Field Analysis. J. Med. Chem. 1993, 36, 70.
52. Oprea, T. I.; Garcia, A. E. Three-Dimensional Quantitative Structure-Activity Relationships of Steroid Aromatase Inhibitors. J. Comput.-Aided Mol. Des. 1996, 10, 186-200.
53. Hansch, C.; Telzer, B. R. and Zhang, L. T. Comparative QSAR in Toxicology: Examples from Teratology and Cancer Chemotherapy of Aniline Mustards. Crit. Rev. Toxicol. 1995, 25, 67-89.
54. Guenard, D.; Gueritte-Voegelein, F.; Potier, P. Taxol and Taxotere: Discovery, Chemistry, and Structure-Activity Relationships. Acc. Chem. Res. 1993, 26, 160-167.
55. Williams, H. J.; Moyna, G.; Scott, A. I. NMR and Molecular Modoling Study of the Conformation of Taxol 2′-Acetate in Chloroform and Dimethyl Sulfoxide Solutions. J. Med. Chem. 1996, 35, 1555-1559.