Structural behaviour of 2-hydroxypropyl-β-cyclodextrin in water: Molecular dynamics simulation studies

Pharmaceutical Research

Volumn 25, Issue 5, 2008, Pages 1092-1099

  Yong, Chin Weng ^a   Washington, Clive ^b   Smith, William ^a  

^a DARESBURY LABORATORY   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

cyclodextrin derivatives; 2 hydroxypropyl; Hydrogen bonding; Molecular dynamics; Water interaction

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; BETA CYCLODEXTRIN; WATER;

AQUEOUS SOLUTION; ARTICLE; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; DRUG STRUCTURE; HYDROGEN BOND; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PRIORITY JOURNAL;

ALGORITHMS; BETA-CYCLODEXTRINS; CHEMISTRY, PHYSICAL; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; GLUCOSE; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR CONFORMATION; WATER;

EID: 42049112995     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-007-9506-y     Document Type: Article

References (29)

1. J. Szejtli. Cyclodextrin Technology. Kluwer, Dordrecht, 1988.
2. J. Szejtli. Introduction and general overview of cyclodextrin chemistry. Chem. Rev 98:1743-1753 (1998).
3. L. Szente, and J. Szejtli. Highly soluble cyclodextrin derivatives: chemistry, properties and trends in development. Adv. Drug Delivery Rev 36:17-28 (1999).
4. L. Szente, and C. E. Strattan. Hydroxypropyl β-Cyclodextrins, Preparation and Physicochemical Properties. Edition de Santé, Paris, 1991.
5. C. J. Betlach, M. A. Gonzalez, B. C. Mckiernan, C. Neff-Davis, and N. Bodor. Oral pharmacokinetics of carbemazepine in dogs from commercial tablets and a cyclodextrin complex. J. Pharm. Sci 82:1058-1060 (1993).
6. W. Löscher, D. Hoenack, A. Richter, H. Schulz, M. Schuerer, R. Duesing, and M. E. Brewster. New injectible aqueous carbamazepine solution through complexing with 2-hydroxypropyl-β-cyclodextrin: Tolerability and pharmacokinetics after intravenous injection in comparison to a glycofurol-based formulation. Epilepsia 36:255-261 (1995).
7. K. BLindner, and W Saenger. Topography of cyclodextrin inclusion complexes. XVI. Cyclic system of hydrogen bonds: structure of α-cyclodextrin hexahydrate, form (II): comparison with form (I). Acta Crystallogr. B 38:203-210 (1982).
8. K. K. Chacko, and W. Saenger. J. Am. Chem. Soc 103:1708(1981).
9. H. -J. Schneider, F. Hacket, and V. Rüdiger. Chem. Rev. 98:1755-1785 (1998).
10. N. S. Bodor, M. J. Huang, and J. D. Watts. J. Pharm. Sci. 84:330(1995).
11. C. S. Nascimento Jr., H. F. Dos Santos, and W. B. De Almeida. Theoretical study of the formation of the α-cyclodextrin hexahydrate. Chem. Phys. Lett 397:422-428 (2004).
12. W. Linert, P. Margl, and F. Renz. Solute-solvent interactions between cyclodextrin and water: a molecular mechanical study. Chem. Phys 161:327-338 (1992).
13. L. Lawtrakul, H. Viernstein, and P. Wolschann. Molecular dynamics simulations of β-cyclodextrin in aqueous solution. Int. J. Pharm 256:33-41 (2003).
14. J. E. H. Koehler, W. Saenger, and W. F. van Gunsteren. Conformational differences between α-cyclodextrin in aqueous solution and in crystalline form. J. Mol. Biol 203:241-250 (1988).
15. R. G. Winkler, S. Fioravanti, G. Ciccotti, C. Margheritis, and M. Villa. Hydration of β-cyclodextrin: A molecular dynamics simulation study. J. Comp-Aided Mol. Design 14:659-667 (2000).
16. M. Fermeglia, M. Ferrone, A. Lodi, and S. Pricl. Host-guest inclusion complexes between anticancer drugs and β-cyclodextrin: computational studies. Carbohydr. Polym 53:15-44 (2003).
17. A. Buvari-Barcza, and L. Barcza. Influence of the guest, the type and degree of substitution on inclusion complex formation of substituted β-cyclodextrins. Talanta 49:577-585 (1999).
18. W. Smith, C. W. Yong, and P. M. Rodger. DL_POLY: Application to molecular simulation. Mol. Sim 28:385-471 (2002).
19. W. L. Jorgensen, J. Chandrasekhar, J. Madura, R. W. Impey, and M. L. Klein. Comparison of simple potential functions for simulating liquid water. J. Chem. Phys 79:926-935 (1983).
20. A. D. MacKerell Jr., J. Wiorkiewicz-Kuczera, and M. Karplus. An All-Atom Empirical Energy Function for the Simulation of Nucleic Acids. J. Am. Chem. Soc 117:11946-11975 (1995).
21. U. Essmann, L. Perera, M. L. Berkowtz, T. Darden, H. Lee, and L. G. Pedersen. A smooth particle mesh Ewald method. J. Chem. Phys 103:8577-8593 (1995).
22. W. Chen, C.-E. Chang, and M. K. Gilson. Calculation of cyclodextrin binding affinities: energy, entropy and implication for drug design. Biophys. J 87:3035-3049 (2004).
23. H. C. Georg, K. Coutinho, and S. Canuto. A look inside the cavity of hydrated α-cyclodextrin: A computer simulation study. Chem. Phys. Lett 414:16-21 (2005).
24. S. Melchionna, G. Ciccotti, and B. L. Holian. Mol. Phys. Hoover NPT dynamics for systems varying in size and shape. Mol. Phys 78:533-544 (1993).
25. K. J. Naidoo, J. Y. Chen, J. L. M. Jansson, G. Widmalm, and A. Maliniak. Molecular properties related to the anomalous solubility of β-cyclodextrin. J. Phys. Chem. B 108:4236-4238 (2004).
26. L. Liu, and Q.-X. Guo. The driving forces in the inclusion complexation of cyclodextrins. J. Inc. Phenom 42:1-14 (2002).
27. J. E. H. Koehler, W. Saenger, and W. F. van Gunsteren. The flip-flop hydrogen bonding phenomenon. Molecular dynamics simulation of crystalline β-cyclodextrin. Eur. Biophys. J 16:153-168 (1988).
28. 2O: a comparative study. Carbohydr. Res 341:270-274 (2006).
29. A. W. Coleman, I. Nicolis, N. Keller, and J. P. Dalbiez. Aggregation of cyclodextrins: An explanation of the abnormal solubility of β-cyclodextrin. J. Inc. Phenom. Mol. Recog. Chemistry 13:139-143 (1992).