Binding, molecular mechanics, and thermodynamics of cyclodextrin inclusion complexes with ketoprofen in aqueous medium

Pharmaceutical Development and Technology

Volumn 3, Issue 3, 1998, Pages 307-313

  Díaz, David ^a   Escobar Lianos, Carolina Marta ^a   Bernad Bernad, María Josefa ^a   Mora, Jesús Gracia ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Direct spectroscopy; Inclusion complexes with cyclodextrins; Ketoprofen; Molecular mechanics; Nuclear magnetic resonance; Thermodynamics

Indexed keywords

ALPHA CYCLODEXTRIN; ANTIINFLAMMATORY AGENT; BETA CYCLODEXTRIN; GAMMA CYCLODEXTRIN; KETOPROFEN;

AQUEOUS SOLUTION; ARTICLE; BINDING KINETICS; COMPLEX FORMATION; DRUG STRUCTURE; HYDROPHOBICITY; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; THERMODYNAMICS; ULTRAVIOLET SPECTROSCOPY;

EID: 0031679890     PISSN: 10837450     EISSN: None     Source Type: Journal    
DOI: 10.3109/10837459809009858     Document Type: Article

References (30)

1. S. Z. Lin, D. Wouessidjewe, M. C. Poelman, and D. Duchêne, Indomethacin and cyclodextrin complexes, Int. J. Pharm., 69, 211-219 (1991).
2. H. Okamoto, H. Kamatsu, M. Hashida, and H. Sezaki, Effects of β-cyclodextrin on the percutaneous absorption of butyl paraben, indomethacin and sulfanilic acid, Int. J. Pharm., 30, 35-45 (1986).
3. K. Uekama, H. Otagiri, A. Sakai, T. Irie, N. Martsuo, and Y. Matsmoka, Improvement in the percutaneous of betomethasone dipropionate by δ-cyclodextrin complexations, J. Pharm. Pharmacol., 37, 532-535 (1985).
4. N. Erden and N. Çelebi, A study of the inclusion complex of naproxen with β-cyclodextrin, Int. J. Pharm., 48, 83-89 (1988).
5. J. Szejtli, Cyclodextrin Technology, Kluwer, Dordrecht, 1988, pp. 186-306.
6. J. Blanco, J. L. Vila-Jato, F. Otero, and S. Anguiano, Influence of method of preparation on inclusion complexes of naproxen with different cyclodetrins, Drug. Dev. Ind. Pharm., 17(7), 943-957 (1991).
7. T. Y. Shen, Non-steroidal anti-inflammatory agents, in Burger's Medicinal Chemistry, Part III (M. E. Wolff, ed.), John Wiley, New York, 1980, pp. 1205-1271.
8. G. G. Liversidge, Ketoprofen, in Analytical Profiles of Drugs Substances, Vol. 10 (K. Florey, ed.), Academic Press, New York, 1981, pp. 443-471.
9. K. A. Connors, Binding Constants. The Measurement of Molecular Complex Stability, John Wiley, New York, 1987, pp. 141-187.
10. J. Ramírez López, A. Cerezo Galán, and I. C. Rodrigucz Galán, Aspectos cinéticos de complejos de inclusión con ciclodextrinas, Cienc. Ind. Farm., 6, 325-332 (1987).
11. S. Glasstone, Termodinámica para Quimicos, 5th ed., Aguilar, Madrid, 1978, pp. 333-385.
12. 1H NMR and molecular modeling study on the inclusion compounds of β-cyclodextrin-indomethacin, J. Org. Chem., 61, 904-914 (1996).
13. D. D. Deranleau, Theory of the measurements of weak molecular complexes. I. General considerations, J. Am. Chem. Soc., 91, 4044-4049 (1969).
14. R. L. Gelb, L. M. Schwartz, R. F. Johnson, and D. A. Laufer, The complexation chemistry of cyclohexaamylose. 4. Reactions of cyclohexaamylose with formic, acetic, and benzoic acid and their conjugated bases, J. Am. Chem. Soc., 101, 1869-1874 (1979).
15. A. Örstan and J. B. Alexander Ross, Investigation of β-cyclodextrin-indole inclusion complex by absorption and fluorescence spectroscopies, J. Phys. Chem., 91, 2739-2745 (1987).
16. S. E. Brown, J. M. Coates, C. J. Easton, S. F. Lincoln, Y. Luo, and A. K. W. Stephens, Cyclodextrin inclusion complexes of two non-steroidal antiinflammatory drugs and of an analgesic drug, Aust. J. Chem., 44, 855-862 (1991).
17. T. Soujanya, T. S. R. Krishna, and A. Samanta, The nature of 4-aminophthalimide-cyclodextrin inclusion complexes, J. Phys. Chem., 96, 8544-8548 (1992).
18. A. Nag, T. Chakrabarty, and K. Bhattacharyya, Effect of γ-cyclodextrin on the intramolecular charge transfer process in aminocoumarin laser dyes, J. Phys. Chem., 94, 4203-4206 (1990).
19. G. Nelson and I. M. Warner, Fluorescence quenching studies of cyclodextrins complexes of pyrene and naphthalene in the presence of alcohols, J. Phys. Chem., 94, 576-581 (1990).
20. J. Szejtli, Cyclodextrin, properties and applications, Drug Invest., 2(suppl. 4), 11-21 (1990).
21. I. Suzuki, Q. Chen, A. Ueno, and T. Osa, Ferrocene-appended cyclodextrins. The effects of temperature, organic solvent, length of spacer, and cavity size on the complexation behavior, Bull. Chem. Soc. Jpn., 66(5), 1472-1481 (1993).
22. R. I. Gelb and L. M. Schwartz, Complexation of carboxylic acids and anions by alpha and beta cyclodextrins, J. Incl. Phenom. Mol. Recog. Chem., 7, 465-476 (1989).
23. S. Hamai, Hydrogen bonding in inclusion complexes of heptakis (2,3,6-tri-O-methyl)-β-cyclodextrin with chlorophenols in organic solvents, Bull. Chem. Soc. Jpn., 65, 2323-2327 (1992).
24. M. Komiyama and M. L. Bender, Importance of apolar binding in complex formation of cyclodextrin with adamantanecarboxylate, J. Am. Chem. Soc., 100, 2259-2260 (1978).
25. R. J. Bergeron, Cycloamylose-sustrate binding, in Inclusion Compounds. Physical Properties and Applications, Vol. 3 (J. L. Atwood, J. E. D. Davies, and D. D. MacNicol, eds.), Academic Press, London, 1984, pp. 391-443.
26. W. P. Jenks, Catalysis in Chemistry and Enzymology, Dover Publications, New York, 1987, pp. 393-436.
27. M. E. Amato, F. Djedaini-Pilord, B. Perly, and G. Scarlata, High field NMR techniques and molecular modelling study of the inclusion complexes of the nootropic drug tehilsetam (CAS-997) in cyclodextrins, J. Chem. Soc. Perkin Trans., 2, 2065-2069 (1992).
28. N. Azaroual-Bellanger and B. Perly, Investigation of the dynamic of cyclodextrins and their inclusion complexes in water by deuterium NMR, Magn. Reson. Chem., 32, 8-11 (1994).
29. M. E. Amato and G. P. Pappalardo, High-field NMR techniques and molecular modelling in the study of the complex of the cognition activator suronacrine (HP-128) with cyclodextrins, Magn. Reson. Chem., 31, 455-460 (1993).
30. C. Boymond and H. Ridolphi, Physico-chemical study of inclusion compound phenothiazine-β-cyclodextrin, Drug. Dev. Ind. Pharm., 20(14), 2183-2193 (1994).