Determination of stability constant of β-cyclodextrin complexes using the membrane permeation technique and the permeation behavior of drug-competing agent-β-cyclodextrin ternary systems

European Journal of Pharmaceutical Sciences

Volumn 8, Issue 2, 1999, Pages 133-139

  Ono, Naomi ^a   Hirayama, Fumitoshi ^a   Arima, Hidetoshi ^a   Uekama, Kaneto ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

Cyclodextrin; Inclusion complex; Membrane permeation; Stability constant

Indexed keywords

BENZOIC ACID DERIVATIVE; BETA CYCLODEXTRIN; PHENACETIN;

ARTICLE; COMPLEX FORMATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MEMBRANE TRANSPORT; PRIORITY JOURNAL; SOLUBILIZATION; TECHNIQUE; THEORY;

ALGORITHMS; BENZOIC ACIDS; BETA-CYCLODEXTRINS; CELLOPHANE; CYCLODEXTRINS; DRUG STABILITY; PERMEABILITY; PHENACETIN; SOLUBILITY;

EID: 0032896477     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0928-0987(99)00002-0     Document Type: Article

References (22)

1. Bender, M.L., Komiyama, M., 1978. Cyclodextrin Chemistry. Springer-Verlag, Berlin, p. 33.
2. Benesi H.A., Hildebrand J.H. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 71:1949;2703-2707.
3. Connors K.A., Lipari J.M. Effect of cycloamyloses on apparent dissociation constants of carboxylic acids and phenols: Equilibrium analytical selectivity induced by complex formation. J. Pharm. Sci. 65:1976;379-383.
4. Cramer F., Saenger W., Spatz H.-Ch. Inclusion compounds; XIX; the formation of inclusion compounds of α-cyclodextrin in aqueous solutions; thermodynamics and kinetics. J. Am. Chem. Soc. 89:1967;14-20.
5. Guttman D.E. Complex formation influence on reaction rate I; effect of caffeine on riboflavin base-catalyzed degradation rate. J. Pharm. Sci. 51:1962;1162-1166.
6. Higuchi T., Connors K.A. Phase-solubility techniques. Adv. Anal. Chem. Instr. 4:1965;117-212.
7. Hirayama, F., Uekama, K., 1987. Methods of investigating and preparing inclusion compounds. In: Duchêne, D. (Ed.), Cyclodextrins and their Industrial Uses. Editions de Santé, Paris, pp. 131-172.
8. Koizumi K., Kubota Y., Okada Y., Utamura T. Microanalyses of β-cyclodextrin in plasma by high-performance liquid chromatography. J. Chromatogr. 341:1985;31-41.
9. Lach J.L., Chin T.F. Interaction of pharmaceuticals with schardinger dextrins III; interactions with mono-halogenated benzoic acids and aminobenzoic acids. J. Pharm. Sci. 53:1964;69-73.
10. Lineweaver H., Burk D. The determination of enzyme dissociation constants. J. Am. Chem. Soc. 56:1934;658-666.
11. Lueck L.M., Wurster D.E., Higuchi T., Lemberger A.P., Busse L.W. Investigation and development of protective ointments I; development of a method for measuring permeation of mechanical barriers. J. Am. Pharm. Assoc. 46:1957;694-698.
12. Martin, A., Swarbrick, J., Cammarata, A., 1983. Physical Pharmacy. Lea and Febiger, Philadelphia, p. 336.
13. Miyaji T., Kurono Y., Uekama K., Ikeda K. Simultaneous determination of complexation equilibrium constants for conjugated guest species by the extended potentiometric titration method on the barbiturate-β-cyclodextrin system. Chem. Pharm. Bull. 24:1976;1155-1159.
14. Ohki, A., Takagi, M., Ueno, K., 1980. Ion transport through liquid membrane driven by redox potential: Multi-component ion carrier as a mediator. Chem. Lett. 1591-1594.
15. Saito, H., Yonemura, H., Nakamura, H., Matsuo, T., 1990. Stability and exchange properties of through-ring cyclodextrin complexes; effects of chain length in polymethylene bis[1-pyridinium] as guest molecules. Chem. Lett. 535-538.
16. Saito Y., Tanemura I., Ueda H., Sato T. Simultaneous determination of the stability constants for fragrance materials with 2-hydroxylpropyl-β-cyclodextrin by static head-space gas chromatography. Chem. Pharm. Bull. 46:1998;1177-1179.
17. Sideris E.E., Georgiou C.A., Koupparis M.A., Macheras P.E. Automated flow-injection serial dynamic dialysis technique in the study of drug binding with cyclodextrins. Anal. Chimica Acta. 289:1994;87-95.
18. Thakkar A.L., Kuehn P.B., Perrin J.H., Wilham W.L. Cycloheptaamylose-barbiturate inclusion complexes; solubility and circular dichroism studies. J. Pharm. Sci. 61:1972;1841-1843.
19. Uekama, K., Hirayama, F., Irie, T., 1978. The new method for determination of the stability constants of cyclodextrin-prostaglandin inclusion complexes by liquid chromatography. Chem. Lett. 661-664.
20. Uekama K., Hirayama F., Irie T. Cyclodextrin drug carrier systems. Chem. Rev. 98:1998;2045-2076.
21. Uekama K., Matsuo N., Hirayama F., Ichibagase H., Arimori K., Tsubaki K., Satake K. Enhanced bioavailability of acetohexamide by β-cyclodextrin complexation. Yakugaku Zasshi. 100:1980;903-909.
22. Yamaoka K., Nakagawa T. A nonlinear least squares program based on differential equations MULTI (Runge), for microcomputers. J. Pharmacobio-Dyn. 6:1983;595-603.