Molecular dynamics simulations of UC781-cyclodextrins inclusion complexes in aqueous solution

European Journal of Pharmaceutical Sciences

Volumn 47, Issue 4, 2012, Pages 752-758

  Boonyarattanakalin, Kanokthip ^a   Wolschann, Peter ^b   Toochinda, Pisanu ^a   Lawtrakul, Luckhana ^a  

^a THAMMASAT UNIVERSITY   (Thailand)

^b UNIVERSITY OF VIENNA   (Austria)

Author keywords

Cyclodextrin; Inclusion complex; Molecular dynamics simulations; UC781

Indexed keywords

N [4 CHLORO 3 (3 METHYL 2 BUTENYLOXY)PHENYL] 2 METHYL 3 FURANCARBOTHIOAMIDE; PHENYL GROUP;

AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; CRYSTAL STRUCTURE; DRUG STABILITY; DRUG STRUCTURE; METHYLATION; MOLECULAR DYNAMICS; PRIORITY JOURNAL; STEREOSPECIFICITY;

ANILIDES; ANTI-HIV AGENTS; BETA-CYCLODEXTRINS; CYCLODEXTRINS; FURANS; MOLECULAR DYNAMICS SIMULATION; SOLUTIONS;

EID: 84866500707     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2012.08.004     Document Type: Article

References (34)

1. M.E. Amato, G.M. Lombardo, G.C. Pappalardo, and G. Scarlata High field NMR techniques, molecular modelling and molecular dynamics simulations in the study of the inclusion complex of the cognition activator (±)-1-(4- methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid (CI-933) with [beta]-cyclodextrin J. Mol. Struct. 350 1995 71 82
2. T. Aree, W. Saenger, P. Leibnitz, and H. Hoier Crystal structure of heptakis(2,6-di-O-methyl)-β-cyclodextrin dihydrate: a water molecule in an apolar cavity Carbohyd. Res. 315 1999 199 205
3. K.S. Boonyarattanakalin, P. Wolschann, and L. Lawtrakul Molecular dynamics of β-CD in water/co-solvent mixtures J. Inclusion Phenom. Macro. Chem. 70 2011 279 290
4. H.J. Buschmann, D. Knittel, and E. Schollmeyer New textile applications of cyclodextrins J. Inclusion Phenom. Mol. Recognit. Chem. 40 2001 169 172
5. Case, D.A., Darden, T.A., Cheatham, I.T.E., Simmerling, C.L., Wang, J., Duke, R.E., Luo, R., Merz, K.M., Pearlman, D.A., Crowley, M., Walker, R.C., Zhang, W., Wang, B., Hayik, S., Roitberg, A., Seabra, G., Wong, K.F., Paesani, F., Wu, X., Brozell, S., Tsui, V., Gohlke, H., Yang, L., Tan, C., Mongan, J., Hornak, V., Cui, G., Beroza, P., Mathew, D.H., Schafmeister, C., Ross, W.S., Kollman, P.A., 2006. AMBER10. University of California, San Francisco, CA.
6. E. Cervelló, F. Mazzucchi, and C. Jaime Molecular mechanics and molecular dynamics calculations of the β-cyclodextrin inclusion complexes with m-, and p-nitrophenyl alkanoates J. Mol. Struct. THEOCHEM 530 2000 155 163
7. R. Challa, A. Ahuja, J. Ali, and R.K. Khar Cyclodextrins in drug delivery: an updated review AAPS Pharm. Sci. Tech. 6 2005 E329 E357
8. K.A. Connors The stability of cyclodextrin complexes in solution Chem. Rev. 97 1997 1325 1357
9. Y. Duan, C. Wu, S. Chowdhury, M.C. Lee, G. Xiong, W. Zhang, R. Yang, P. Cieplak, R. Luo, T. Lee, J. Caldwell, J. Wang, and P. Kollman A point-charge force field for molecular mechanics simulations of proteins based on condensed-phase quantum mechanical calculations J. Comput. Chem. 24 2003 1999 2012
10. M.I. El-Barghouthi, C. Jaime, N.A. Al-Sakhen, A.A. Issa, A.A. Abdoh, M.M. Al Omari, A.A. Badwan, and M.B. Zughul Molecular dynamics simulations and MM-PBSA calculations of the cyclodextrin inclusion complexes with 1-alkanols, para-substituted phenols and substituted imidazoles J. Mol. Struct. THEOCHEM 853 2008 45 52
11. U. Essmann, L. Perera, M.L. Berkowitz, T. Darden, H. Lee, and L.G. Pedersen A smooth particle mesh Ewald method J. Chem. Phys. 103 1995 8577 8593
12. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G., Scuseria, E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., Pople, J.A. 2004. Gaussian 03, Revision C.02 ed. Gaussian, Inc., Wallingford, CT.
13. Y.C. Guillaume, and C. Guinchard New statistical approach to a gas chromatography retention model: application to dichlorophenol isomers J. Phys. Chem. B 101 1997 8390 8394
14. A. Harada Cyclodextrin-based molecular machines Acc. Chem. Res. 34 2001 456 464
15. Y. Ikeda, S. Motoune, T. Matsuoka, H. Arima, F. Hirayama, and K. Uekama Inclusion complex formation of captopril with α- and β-cyclodextrins in aqueous solution: NMR spectroscopic and molecular dynamic studies J. Pharm. Sci. 91 2002 2390 2398
16. W.L. Jorgensen, J. Chandrasekhar, J.D. Madura, R.W. Impey, and M.L. Klein Comparison of simple potential functions for simulating liquid water J. Chem. Phys. 79 1983 926 935
17. K. Kano, and H. Hasegawa Interactions with charged cyclodextrins and chiral recognition J. Inclusion Phenom. Mol. Recognit. Chem. 41 2001 41 47
18. K. Lindner, and W. Saenger Crystal and molecular structure of cyclohepta-amylose dodecahydrate Carbohyd. Res. 99 1982 103 115
19. S. Monti, and S. Sortino Photoprocesses of photosensitizing drugs within cyclodextrin cavities Chem. Soc. Rev. 31 2002 287 300
20. G. Raffaini, F. Ganazzoli, L. Malpezzi, C. Fuganti, G. Fronza, W. Panzeri, and A. Mele Validating a strategy for molecular dynamics simulations of cyclodextrin inclusion complexes through single-crystal x-ray and NMR experimental data: a case study J. Phys. Chem. B 113 2009 9110 9122
21. J. Ren, R.M. Esnouf, A.L. Hopkins, J. Warren, J. Balzarini, D.I. Stuart, and D.K. Stammers Crystal structures of HIV-1 reverse transcriptase in complex with carboxanilide derivatives Biochemistry 37 1998 14394 14403
22. J.P. Ryckaert, G. Ciccotti, and H.J.C. Berendsen Numerical integration of the cartesian equations of motion of a system with constraints: molecular dynamics of n-alkanes J. Comput. Phys. 23 1977 327 341
23. J. Shao, S.W. Tanner, N. Thompson, and T.E. Cheatham Iii Clustering molecular dynamics trajectories: 1. Characterizing the performance of different clustering algorithms J. Chem. Theor. Comput. 3 2007 2312 2334
24. L. Song, and W.C. Purdy Cyclodextrins and their applications in analytical chemistry Chem. Rev. 92 1992 1457 1470
25. J. Szejtli The properties and potential uses of cyclodextrin derivatives J. Inclusion Phenom. Mol. Recognit. Chem. 14 1992 25 36
26. J. Szejtli Introduction and general overview of cyclodextrin chemistry Chem. Rev. 98 1998 1743 1754
27. J. Szejtli Cyclodextrin complexed generic drugs are generally not bio-equivalent with the reference products: therefore the increase in number of marketed drug/cyclodextrin formulations is so slow J. Inclusion Phenom. 52 2005 1 11
28. L. Szente, and J. Szejtli Cyclodextrins in pesticides J. Szejtli, T. Osa, Comprehensive Supramolecular Chemistry 1996 Pergamon Oxford 503 514
29. K. Takahashi Organic reactions mediated by cyclodextrins Chem. Rev. 98 1998 2013 2034
30. F.P. Tomasella, Z. Pan, and L.J.C. Love Effects of selected alcohols on chiral recognition via cyclodextrin inclusion complexation J. Supramol. Chem. 1 1992 25 30
31. K. Uekama Recent aspects of pharmaceutical application of cyclodextrins J. Inclusion Phenom. Mol. Recognit. Chem. 44 2002 3 7
32. A. Vyas, and S. Saraf Cyclodextrin based novel drug delivery systems J. Inclusion Phenom. Macrocyclic Chem. 62 2008 23 42
33. H. Yang, M.A. Parniak, C.E. Isaacs, S.L. Hillier, and L.C. Rohan Characterization of cyclodextrin inclusion complexes of the anti-HIV non-nucleoside reverse transcriptase inhibitor UC781 AAPS J. 10 2008 606 613
34. K. Yin, Q. Xia, D. Xu, and C. Chen Constrain molecular dynamics simulation of 1:1 inclusion of β-cyclodextrin and p-cresol in nanodrip and vacuum systems Chin. J. Chem. Phys. 17 2004 711 716