Development of improved empirical models for estimating the binding constant of a β-cyclodextrin inclusion complex

Pharmaceutical Research

Volumn 26, Issue 1, 2009, Pages 161-171

  Chari, Ravi ^a   Qureshi, Farooq ^b   Moschera, John ^b   Tarantino, Ralph ^b   Kalonia, Devendra ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b HOFFMANN LA ROCHE INC   (United States)

Author keywords

Binding; Cyclodextrins; Descriptors; Empirical; Models

Indexed keywords

BETA CYCLODEXTRIN;

AQUEOUS SOLUTION; ARTICLE; BINDING AFFINITY; COMPLEX FORMATION; CORRELATION COEFFICIENT; DISPERSION; DRUG SOLUBILITY; DRUG STRUCTURE; ELECTRON; LIGAND BINDING; LIPOPHILICITY; MULTIPLE LINEAR REGRESSION ANALYSIS; PARTIAL LEAST SQUARES REGRESSION; PRIORITY JOURNAL;

BETA-CYCLODEXTRINS; CHEMISTRY, PHARMACEUTICAL; DATABASES, FACTUAL; ELECTRONS; EXCIPIENTS; LEAST-SQUARES ANALYSIS; LIGANDS; LIPIDS; MODELS, CHEMICAL; MODELS, STATISTICAL; MOLECULAR WEIGHT; PHARMACEUTICAL PREPARATIONS; REPRODUCIBILITY OF RESULTS; SOLUBILITY; SUBJECT HEADINGS;

EID: 57749181992     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-008-9733-x     Document Type: Article

References (39)

1. R. Challa A. Ahuja J. Ali R. K. Khar 2005 Cyclodextrins in drug delivery: an updated review AAPS PharmSciTech. 6 E329 E357
2. T. Loftsson D. Duchene 2007 Cyclodextrins and their pharmaceutical applications Int. J. Pharm. 329 1 11
3. K. Connors 1997 The stability of cyclodextrin complexes in solution Chem. Rev. 97 1325 1357
4. K. Uekama F. Hirayama T. Irie 1998 Cyclodextrin drug carrier systems Chem. Rev. 98 2045 2076
5. V. J. Stella R. A. Rajewski 1997 Cyclodextrins: their future in drug formulation and delivery Pharm. Res. 14 556 567
6. J. Pitha J. Pitha 1985 Amorphous water-soluble derivatives of cyclodextrins: nontoxic dissolution enhancing excipients J. Pharm. Sci. 74 987 990
7. G. Piel, I. Delneuville, and L. Delattre. In J. Szejtli and L. Szente (eds.), Proc. Eighth Int. Symp. on Cyclodextrins, Kluwer Academic, Dordrecht, 1996, pp. 487-490.
8. J. Szejtli 2004 Past, present, and future of cyclodextrin research Pure Appl. Chem. 76 1825 1845
9. I. Shehatta A. H. Al-Marzouqi B. Jobe A. Dowaidar 2005 Enhancement of aqueous solubility of itraconazole by complexation with cyclodextrins using supercritical carbon dioxide Can. J. Chem. 83 1833 1838
10. T. Loftsson 2002 Cyclodextrins and the biopharmaceutics classification system of drugs J. Inclusion Phenom. Macrocyclic Chem. 44 63 67
11. T. Suzuki M. Ishida W. M. F. Fabian 2000 Classical QSAR and comparative molecular field analyses of the host-guest interaction of organic molecules with cyclodextrins J. Comput.-Aided Mol. Des. 14 669 678
12. C. T. Klein D. Polheim H. Viernstein P. Wolschann 2000 A method for predicting the free energies of complexation between β-cyclodextrin and guest molecules J. Incl. Phenom. Macrocycl. Chem. 36 409 423
13. C. T. Klein D. Polheim H. Viernstein P. Wolschann 2000 Predicting the free energies of complexation between cyclodextrins and guest molecules: linear versus nonlinear models Pharm. Res. 17 358 365
14. T. Suzuki 2001 A nonlinear group contribution method for predicting the free energies of inclusion complexation of organic molecules with α- and β-cyclodextrins J. Chem. Inf. Comput. Sci. 41 1266 1273
15. A. R. Katritzky D. C. Fara H. Yang M. Karelson T. Suzuki V. P. Solov'ev A. Varnek 2004 Quantitative structure-property relationship modeling of β-cyclodextrin complexation free energies J. Chem. Inf. Comput. Sci. 44 529 541
16. Talete srl, DRAGON for Windows (Software for Molecular Descriptor Calculations). Version 5.4-2006- http://www.talete.mi.it/.
17. R. Todeschini, and V. Consonni. Handbook of molecular descriptors. Wiley-VCH, Weinheim (Germany), 2000.
18. M. V. Rekharsky R. N. Goldberg F. P. Schwarz Y. B. Tewari P. D. Ross Y. Yamashoji Y. Inoue 1995 Thermodynamic and nuclear magnetic resonance study of the interactions of alpha- and beta-cyclodextrin with model substances: phenethylamine, ephedrines, and related substances J. Am. Chem. Soc. 117 8830 8840
19. A. K. Ghose G. M. Crippen 1986 Atomic physicochemical parameters for three-dimensional structure-directed quantitative structure-activity relationships I. Partition coefficients as a measure of hydrophobicity J. Comput. Chem. 7 565 577
20. P. Ertl B. Rohde P. Selzer 2000 Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties J. Med. Chem. 43 3714 3717
21. Y. Inoue T. Hakushi Y. Liu L. Tong B. Shen D. Jin 1993 Thermodynamics of molecular recognition by cyclodextrins. 1. Calorimetric titration of inclusion complexation of naphthalenesulfonates with alpha-, beta-, and gamma-cyclodextrins: enthalpy-entropy compensation J. Am. Chem. Soc. 115 475 481
22. E. Junquera V. G. Baonza E. Aicart 1999 Energetics of the encapsulation of o-, m-, and p-hydroxybenzoic acids by β-cyclodextrin and its methylated and hydroxypropylated derivatives in aqueous solution Can. J. Chem. 77 348 355
23. K. Rajendrakumar T. Pralhad S. Madhusudan 2004 Comparative study on co-ground products of rofecoxib with β-cyclodextrin and its sulfobutyl ether-7 derivative in solution and in the solid state J. Inclusion Phenom. Macrocyclic Chem. 49 259 266
24. K. Uekama Y. Hieda F. Hirayama H. Arima M. Sudoh A. Yagi H. Terashima 2001 Stabilizing and solubilizing effects of sulfobutyl ether β-cyclodextrin on prostaglandin e1 analogue Pharm. Res. 18 1578 1585
25. P. Wallimann T. Marti A. Furer F. Diederich 1997 Steroids in molecular recognition Chem. Rev. 97 1567 1608
26. T. X. Xiang B. D. Anderson 1990 Inclusion complexes of purine nucleosides with cyclodextrins: II, Investigation of inclusion complex geometry and cavity microenvironment Int. J. Pharm. 59 45 55
27. R. Carpignano M. Marzona E. Cattaneo S. Quaranta 1997 QSAR study of inclusion complexes of heterocyclic compounds with β-cyclodextrin Anal. Chim. Acta. 348 489 493
28. L. Liu Q.-X. Guo 1999 Wavelet neural network and its application to the inclusion of β-cyclodextrin with benzene derivatives J. Chem. Inf. Comput. Sci. 39 133 138
29. L. Liu Q.-X. Guo 1999 Novel prediction for the driving force and guest orientation in the complexation of α- and β-cyclodextrin with benzene derivatives J. Phys. Chem. B. 103 3461 3467
30. Y. Matsui T. Nishioka T. Fujita 1985 Quantitative structure-reactivity analysis of the inclusion mechanism by cyclodextrins Top. Curr. Chem. 128 61 89
31. J. H. Park T. H. Nah 1994 Binding forces contributing to the complexation of organic molecules with β-cyclodextrin in aqueous solution J. Chem. Soc. Perkin Trans. 2 1359 1362
32. P. Geladi B. R. Kowalski 1986 Partial least-squares regression: a tutorial Anal. Chim. Acta. 185 1 17
33. R. Kramer. Chemometric techniques for quantitative analysis. Marcel Dekker, New York, 1998.
34. W. Chen C.-E. Chang M. K. Gilson 2004 Calculation of cyclodextrin binding affinities: energy, entropy, and implications for drug design Biophys. J. 87 3035 3049
35. G. L. Bertrand J. R. Faulkner S. M. Han D. W. Armstrong 1989 Substituent effects on the binding of phenols to cyclodextrins in aqueous solution J. Phys. Chem. 93 6863 6867
36. 7M-β-CD to HP-β-CD Pharm. Res. 18 667 673
37. T. Higuchi K. Connors 1965 Phase-solubility techniques Adv. Anal. Chem. Instrum. 4 117 212
38. A. Yasri D. Hartsough 2001 Toward an optimal procedure for variable selection and QSAR model building J. Chem. Inf. Comput. Sci. 41 1218 1227
39. A. Trapani A. Lopedota N. Denora V. Laquintana M. Franco A. Latrofa G. Trapani 2005 A rapid screening tool for estimating the potential of 2-hydroxypropyl-β-cyclodextrin complexation for solubilization purposes Int. J. Pharm. 295 163 175