Influence of lipophilicity on drug-cyclodextrin interactions: A calorimetric study

Thermochimica Acta

Volumn 511, Issue 1-2, 2010, Pages 102-106

  Waters, Laura J ^a   Bedford, Susan ^a   Parkes, Gareth M B ^a   Mitchell, J C ^b  

^a UNIVERSITY OF HUDDERSFIELD   (United Kingdom)

^b UNIVERSITY OF GREENWICH   (United Kingdom)

Author keywords

Cyclodextrin complex; Drug; Isothermal; ITC; log P; NSAID; Thermodynamic

Indexed keywords

DRUG; ISOTHERMAL; ITC; LOG P; NSAID;

BINDING ENERGY; CALORIMETRY; CYCLODEXTRINS; DRUG PRODUCTS; ENTHALPY; FREE ENERGY; GIBBS FREE ENERGY; SILANES; STOICHIOMETRY; THERMODYNAMICS;

DRUG INTERACTIONS;

EID: 78149283652     PISSN: 00406031     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tca.2010.07.031     Document Type: Article

References (45)

1. J. Szejtli Cyclodextrins in drug formulations: I Pharm. Tech. Int. 3 1991 15 22
2. D. Diaz, C.M. Escobar Llanos, and M.J.B. Bernad Study of the binding in an aqueous medium of inclusion complexes of several cyclodextrins involving fenoprofen calcium Drug Dev. Ind. Pharm. 25 1999 107 110
3. N. Nesna, J. Lou, and R. Breslow The binding of cocaine to cyclodextrins Bioorg. Med. Chem. Lett. 10 2000 1931 1933
4. M.E.A. Dalmora, and A.G. Oliveira Inclusion complex of piroxicam with beta-cyclodextrin and incorporation in hexadecyltrimethylammonium bromide based microemulsion Int. J. Pharm. 184 1999 157 164
5. G. Bettinetti, A. Gazzaniga, P. Mura, F. Giordano, and M. Setti Thermal behavior and dissolution properties of naproxen in combinations with chemically modified beta-cyclodextrins Drug Dev. Ind. Pharm. 18 1992 39 53
6. G. Bettinetti, P. Mura, M.T. Faucci, M. Sorrenti, and M. Setti Interaction of naproxen with noncrystalline acetyl beta- and acetyl gamma-cyclodextrins in the solid and liquid state Eur. J. Pharm. Sci. 15 2002 21 29
7. A. Mallick Rotational relaxation dynamics of β-carboline analogue in cyclodextrin nanocavity: How does the cavity size barricade the molecular rotation? J. Mol. Struct. 934 2009 91 95
8. M.R. Eftink, M.L. Andy, K. Bystrom, H.D. Perlmutter, and D.S. Kristol Cyclodextrin inclusion complexes: studies of the variation in the size of alicyclic guests J. Am. Chem. Soc. 111 1989 6765 6772
9. 1-substituted sulphonamides from water to chloroform J. Chem. Soc. Faraday Trans. 88 1992 1665 1668
10. N.A. Todorova, and F.P. Schwarz The role of water in the thermodynamics of drug binding to cyclodextrin J. Chem. Thermodyn. 39 2007 1038 1048
11. I. Gomez-Orellana, and D. Hallen The thermodynamics of the binding of benzene to β-cyclodextrin in aqueous solution Thermochim. Acta 221 1993 183 193
12. S. Takagi, M. Fujisawa, and T. Kimura Tight inclusion-complex formation with negative entropy change by 1-hexanol molecules into α-cyclodextrin cavities in aqueous solutions Chem. Express 6 1991 93 96
13. S. Takagi, and M. Maeda Calorimetric determination of enthalpies, Gibbs energies and entropies of inclusion of some alcohols into α- and β-cyclodextrins in aqueous solutions J. Inclusion Phenomena 2 1984 775 780
14. S. Takagi, M. Fujisawa, and T. Kimura Enthalpy and entropy changes on molecular inclusion of 1,3-butanediol into α- and β-cyclodextrins cavities in aqueous solutions Thermochim. Acta 183 1991 289 297
15. L.E. Briggner, X.R. Ni, F. Tempesti, and I. Wadso Microcalorimetric titration of β-cyclodextrin with adamantine-1-carboxylate Thermochim. Acta 109 1986 139 143
16. E. Siimer, and K. Kurvits Calorimetric studies of benzoic acid-cyclodextrin inclusion complexes Thermochim. Acta 140 1989 161 168
17. E. Siimer, M. Kurvits, and A. Kostner Thermochemical investigation of β-cyclodextrin complexes with benzoic acid and sodium benzoate Thermochim. Acta 116 1987 249 256
18. K. Matsuyama, S. El-Gizawy, and J.H. Perrin Thermodynamic of binding of aromatic acids to α-, β- and γ-cyclodextrins Drug Dev. Ind. Pharm. 13 1987 2687 2691
19. G. Castronuovo, V. Elia, D. Fessas, A. Giordano, and F. Velleca Thermodynamics of the interaction of cyclodextrins with aromatic α-, ω-amino acids in aqueous solutions: a calorimetric study at 25 °C Carbohydr. Rev. 272 1995 31 39
20. W. Hirsch, T. Muller, R. Pizer, and P.J. Ricatto Complexation of glucose by α- and β-cyclodextrins Can. J. Chem. 73 1995 12 15
21. D. Moelands, N.A. Karnik, R.J. Prankerd, K.B. Sloan, H.W. Stone, and J.H. Perrin Microcalorimetric study of the interaction of aspartame with β-cyclodextrin and hydroxypropyl-β-cyclodextrin: the anomalous heat of dilution of the latter Int. J. Pharm. 86 1992 263 265
22. M.V. Rekharsky, F.P. Schwarz, Y.B. Tewari, and R.N. Goldberg A thermodynamic study of the reactions of cyclodextrins with primary and secondary aliphatic alcohols, with D- and L-phenylalanine and with L-phenylalanineamide J. Phys. Chem. 98 1994 10282 10288
23. M.V. Rekharsky, M.P. Mayhew, R.N. Goldberg, P.D. Ross, Y. Yamashoji, and Y. Inoue Thermodynamic and nuclear magnetic resonance study of the reactions of α- and β-cyclodextrin with acids, aliphatic amines and cyclic alcohols J. Phys. Chem. B 101 1997 87 100
24. E. Siimer, M. Kobu, and M. Kurvits Thermochemical study of cyclodextrin inclusion complexes Thermochim. Acta 170 1990 89 95
25. M.V. Rekharsky, E.V. Nemykina, A.V. Eliseev, and A.K. Yatsimirsky Thermodynamics of molecular recognition of nitrogen heterocycles. Part 1: Interaction of imidazole and imidazolium cation with α-cyclodextrin and β-cyclodextrin Thermochim. Acta 202 1992 25 33
26. P.D. Ross, and M.V. Rekharsky Thermodynamics of hydrogen bond and hydrophobic interactions in cyclodextrin complexes Biophys. J. 71 1996 2144 2154
27. Y. Inoue, T. Hakushi, Y. Liu, L.H. Tong, B.J. Shen, and D.S. Jins Thermodynamics of molecular recognition by cyclodextrins.1. Calorimetric titration of inclusion complexation of naphthalenesulfonates with cy-, 6-, and y-cyclodextrins: enthalpy-entropy compensation J. Am. Chem. Soc. 115 1993 475 481
28. W. Linert, L.F. Han, and I. Lukovits The use of the isokinetic relationship and molecular mechanics to investigate molecular interactions in inclusion complexes of cyclodextrins Chem. Phys. 139 1989 441 455
29. D. Hallen, A. Schon, I. Shehatta, and I. Wadso Microcalorimetric titration of α-cyclodextrin with some straight-chain alkan-1-ols at 288.15 and 308.15K J. Chem. Soc. Faraday Trans. 88 1992 2859 2863
30. G. Barone, G. Castronuovo, P. Del Vecchio, V. Elia, and M. Muscetta Thermodynamics of formation of inclusion compounds in water J. Chem. Soc. Faraday Trans. 1 88 1986 2089 2101
31. W.Q. Tong, J.L. Lach, T.F. Chin, and J.K. Guillory Structural effects on the binding if amine drugs with the diphenylmethyl functionality to cyclodextrins. I. A microcalorimetric study Pharm. Res. 8 1991 951 957
32. R.I. Gelb, S. Raso, and J.S. Alper Complexation reactions of β-cyclodextrin, per-(2,3,6-O-methyl) cycloheptaamylose and γ-cyclodextrin with phenolphthalein, adamantine carboxylate and adamantine acetate Supramol. Chem. 4 1995 279 285
33. M.V. Rekharsky, and Y. Inoue Complexation thermodynamics of cyclodextrins Chem. Rev. 98 1998 1875 1917
34. S.F. Lin, and K.A. Connors Complex formation between α-cyclodextrin and 4-substituted phenols studied by potentiometric and competitive spectrophotometric methods J. Pharm. Sci. 72 1983 1333 1338
35. A. Ueno Detection of organic compounds by guest-responsive circular dichroism variation of ferrocene-appended cyclodextrins Anal. Chem. 64 1992 1650 1655
36. A.F. Casy Chiral discrimination by NMR spectroscopy Trends. Analyt. Chem. 12 1993 185 189
37. M.L. Vazquez, C.M. Franco, A. Cepeda, P. Prognon, and G. Mahuzier Liquid chromatographic study of the interaction between aflatoxins and β-cyclodextrin Anal. Chim. Acta 269 1992 239 247
38. S.G. Penn, E.T. Bergstrom, D.M. Goodall, and J.S. Loran Capillary electrophoresis with chiral selectors: optimization of separation and determination of thermodynamic parameters for binding of tioconazole enantiomers to cyclodextrins Anal. Chem. 66 1994 2866 2873
39. A. Aversa, W. Etter, R.I. Gelb, and L.M. Schwartz Complexation of aliphatic dicarboxylic acids and anions by alpha-cyclodextrin J. Incl. Phenom. Mol. Recog. Chem. 9 1990 277 285
40. J.L. Lach, and W.A. Pauli Interaction of pharmaceuticals with Schardinger dextrins, interaction of β-cyclodextrin, sodium deoxycholate, and deoxycholic acid with amines and pharmaceutical agents J. Pharm. Sci. 55 1966 32 38
41. A.F. Danil de Namor Application of calorimetry (macro and micro) to the study of host-guest interactions in solution Indian J. Technol. 30 1992 593 603
42. L. Waters, S.E.A. Leharne, and J.C. Mitchell Saturation determination of micellar systems using isothermal titration calorimetry J. Thermal Anal. Calorim. 80 2005 43 47
43. S. Xing, Q. Zhang, C. Zhang, Q. Zhao, H. Ai, and D. Sun Isothermal titration calorimetry and theoretical studies on host-guest interaction of ibuprofen with α-, β- and γ-cyclodextrin J. Solution Chem. 38 2009 531 543
44. E. Beetge, J. du Plessis, D.G. Muller, C. Goosen, and F.J. van Rensburg The influence of the physicochemical characteristics and pharmacokinetic properties of selected NSAID's on their transdermal absorption Int. J. Pharm. 193 2000 261 264
45. Q. Li, H. Tsuji, Y. Kato, Y. Sai, Y. Kubo, and A. Tsuji Characterisation of the transdermal transport of flurbiprofen and indomethacin J. Contr. Rel. 110 2006 542 556