Ab initio conformational study of the phenylisoserine side chain of paclitaxel

Journal of Medicinal Chemistry

Volumn 42, Issue 2, 1999, Pages 291-299

  Milanesio, Marco ^a   Ugliengo, Piero ^a   Viterbo, Davide ^a   Appendino, Giovanni ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; PACLITAXEL;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CHEMOTHERAPY; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PACLITAXEL; SOLVENTS;

EID: 0032937808     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm981082t     Document Type: Article

References (34)

1. Nicolaou, K. C.; Dai, W. M.; Guy R. K. Chemistry and Biology of Taxol. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44.
2. Chen, S. H.; Farina, V. The chemistry and pharmacology of Paclitaxel and its derivatives; Elsevier: Amsterdam, 1995.
3. Barboni, L.; Gariboldi, P.; Appendino, G.; Enriù, R.; Gabetta, B.; Bombardelli, E. New Taxoids from Taxus baccata. Liebigs Ann. 1995, 345.
4. 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.
5. Gueritte-Voegelein, F.; Guenard, D.; Mangatal, L.; Potier, P.; Guilhem, J.; Cesario, M.; Pascard, C. Structure of a Synthetic Taxol Precursor: N-tert-Butoxycarbonyl-10-deacetyl-N-debenzoyltaxol. Acta Crystallogr. 1990, C46, 781-784.
6. Gao, Q.; Parker, W. L. The "Hydrophobic Collapse" Conformation of Paclitaxel (Taxol) Has Been Observed in a Nonaqueous Environment: Crystal Structure of 10-Deacetyl-7-epitaxol. Tetrahedron 1996, 52, 2291-2300.
7. Gao, Q.; Chen, S. H. An Unprecedented side Chain Conformation of Paclitaxel (Taxol): Crystal Structure of 7-Mesylpaclitaxel. Tetrahedron Lett. 1996, 37, 3425-3428.
8. 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.
9. Gao, Q.; Golik, J. 2′-Carbamate Taxol. Acta Crystallogr. 1995, C51, 295-298.
10. Miller, R. W.; Powell, R. G.; Smith, C. R., Jr.; Arnold, E.; Clardy, J. Antileukemic Alkaloids from Taxus wallichiana Zucc. J. Org. Chem. 1981, 46, 1469-1474.
11. Peterson, J. R.; Do, H. D.; Rogers, R. D. X-ray Structure and Crystal Lattice Interactions of the Taxol Side-Chain Methyl Ester. Pharm. Res. 1991, 8, 908-912.
12. Williams, H. J.; Scott, A. I.; Dieden, R. A.; Swindell, C. S.; Chirlian, L. E.; Francl, M. M.; Heerding, J. M.; Krauss, N. E. NMR and Molecular Modeling Study of the Conformations of Taxol and of its Side Chain Methyl Ester in Aqueous and Non-Aqueous Solution. Tetrahedron 1993, 49, 6545-6560.
13. Williams, H. J.; Moyna, G.; Scott, A. I.; Swindell, C. S.; Chirlian, L. E.; Heerding, J. M.; Williams, D. K. NMR and Molecular Modeling Study of the Conformations of Taxol 2′-Acetate in Chloroform and Aqueous Dimethyl Sulfoxide Solutions. J. Med. Chem. 1996, 39, 1555-1559.
14. Dubois, J.; Gue′nard, 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.
15. Williams, H. J.; Scott, A. I.; Dieden, R. A.; Swindell, C. S.; Chirlian, L. E.; Francl, M. M.; Heerding, J. M.; Krauss, N. E. NMR and Molecular Modeling Study of Active and Inactive Taxol Analogues in Aqueous and Nonaqueous Solution. Can. J. Chem. 1994, 72, 252-260.
16. Łoz̀yǹski, M.; Rusińska-Roszak, D. PM3 Conformations of C-13 Taxol Side Chain Methyl Ester. Tetrahedron Lett. 1995, 36, 8849-8852.
17. Vander Velde, D. G.; Georg, G. I.; Grunewald, G. L.; Gunn, C. D.; Mitsher, L. A. "Hydrophobic Collapse" of Taxol and Taxotere Solution Conformations in Mixtures of Water and Organic Solvent. J. Am. Chem. Soc. 1993, 115, 11650-11651.
18. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Wong, M. W.; Foresman, J. B.; Robb, M. A.; Head-Gordon, M.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92/DFT, revision G.3; Gaussian, Inc.: Pittsburgh, PA, 1993.
19. (b) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, revision C.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
20. Clark, M.; Cramer, R. D., III; Van Opdenbosch, N. Validation of the General Purpose Tripos 5.2 Force Field. J. Comput. Chem. 1989, 10, 982-1012.
21. Spartan IBM, version 5.0.2 X11 AIX 4.1.4; Wavefunction Inc., 1997.
22. (a) Tatewaki, H.; Huzinaga, S. A Systematic Preparation of New-Contracted Gaussian-Type Orbital Sets. III. Second Row Atoms from Lithium trough Neon. J. Comput. Chem. 1980, 7, 205-228.
23. (b) Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio molecular orbital theory, 1st ed.; John Wiley & Sons: New York, 1986; Chapter 4.
24. (a) Stewart, J. J. P. Optimization of Parameters for Semiempirical Methods I. Method. J. Comput. Chem. 1989, 10, 209-220.
25. (b) Stewart, J. J. P. Optimization of Parameters for Semiempirical Methods II. Applications. J. Comput. Chem. 1989, 10, 221-264.
26. Onsager, L. Electric Moments of Molecules in Liquids. J. Am. Chem. Soc. 1936, 58, 1486-1493.
27. Ugliengo, P.; Viterbo, D.; Chiari, G. MOLDRAW: Molecular Graphics on a Personal Computer. Z. Kristallog. 1993, 207, 9-23. Available at http://www.ch.unito.it/ifm/fisica/moldraw/ moldraw.html.
28. Allen, F. H.; Kennard, O. 3D Search and Research Using the Cambridge Structure Database. Chem. Des. Automation News 1993, 8, 1, 31-37.
29. (a) Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; 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 Analogues. J. Med. Chem. 1994, 37, 3337-3343.
30. (b) Appendino, G. Unpublished data and indication by one of the reviewers.
31. (c) Vander Velde, D. G. Private communication to G.A. and indication by one of the reviewers.
32. Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vander Velde, D. G.; Himes, R. H. Synthesis, Conformational Analysis, and Biological Evaluation of Heteroaromatic Taxanes. J. Org. Chem. 1996, 61, 2664-2676.
33. Ojima, I.; Scott, D. K.; Chakravarty, S.; Ourevitch, M.; Begué, J. P. A Novel Approach to the Study of Solution Structures and Dynamic Behavior of Paclitaxel and Docetaxel Using Fluorine-Containing Analogues as Probes. J. Am. Chem. Soc. 1997, 119, 5519-5527.
34. Nogales, E.; Wolf, S. G.; Downing, K. H. Structure of the αβ Tubulin Dimer by Electron Crystallography. Nature 1998, 391, 199-203.