Summary
In the course of systematic studies on the solubility, hydrophobicity and complexation properties of cyclodextrins and modified cyclodextrins, the retention behavior of α, β, γ and of some glycosylated cyclodextrins has been examined by means of reverse phase HPLC. Mobile phase mixtures containing large amounts of water have been used because of the possible application of such systems to biological studies. Mobile phase mixtures with both methanol and acetonitrile show a linear relationship between the volume fraction of the organic part of the mobile phase and the logarithm of the capacity factor. The extrapolation of capacity factors to a total aquous system are used and compared to other techniques (including solubility) in order to evaluate the hydrophobic properties of the cyclodextrins. In particular, the solubility of cyclodextrins has been explored for a wide range of organic solvent/water mixtures. Whilst β cyclodextrins are definitely the most hydrophobic, followed by glycosylated β cyclodextrins, the others behave differently in the two mobile phase systems. The differences observed in the results are related to the chemical nature of the organic phase. Comparisons between chromatographic and solubility methods are given and interpretations are proposed. Some cyclodextrins have been modified to increase or modify not only the hydrophobicity but also the solubility, the complexation and the molecular recognition of drugs. The most important aim of this study was to define conditions and rules for further drug vectorization by cyclodextrin-drug complexation.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
W. Saenger, Angew. Chem. Int. Ed. Engl.19, 344 (1980)
Proceedings of the First Int. Symp. on Cyclodextrins, J. Szejtli, Akademiai Kiado ed., Budapest, 469 (1982)
P. E. Shaw, C. W. Wilson, J. Food. Sci.,50, 1205 (1985)
W. L. Hinze, Sep. Purif. Methods10, 159 (1981)
R. Smolková, J. Chromatogr.251, 1734 (1982)
D. Duchène, ed. Cyclodextrins and their Industrial uses, Editions de Santé, Paris, 1987.
H. Parrot-Lopez, H. Galons, A. W. Coleman, J. Mahuteau, M. Miocque, Tetrahedron Lett. In press.
H. Parrot-Lopez, A. W. Colemann, Personal communication.
J. Montreuil, Adv. Carbohydr. Chem. Biochem.37, 157 (1980)
R. Kaliszan, Anal. Chem.16, 323 (1986)
R. Collander, Acta Chem. Scand.5, 774 (1951)
E. Tomlinson, J. Chromatogr.113, 1 (1975)
R. Kaliszan, J. Chromatogr. Sci.22, 362 (1984)
A. K. Chatjigakis, C. Donzé, A. W. Coleman, Ph. J. P. Cardot, Anal. chem.14, 1632 (1992)
A. W. Coleman, A. K. Chatjikgakis, Ph. J. P. Cardot, Pol. J. Chem. in press.
D. French, M. L. Levine, J. H. Pazur, E. Norberg, J. Am. Chem. Soc.,71, 353 (1949).
L. R. Snyder, J. W. Dolan, J. R. Gant, J. Chromatogr.165, 3 (1979)
K. W. Street, J. Liq. Chromatogr.10, 655 (1987)
D. C. Locke, J. Chromatogr. Sci.12, 433 (1974)
T. Hanai, J. Chromatogr.550, 313 (1991)
K. Koizumi, Y. Kubota, Y. Okada, T. Utamura, S. Hizukuri, J. I. Abe, J. Chromatogr.437, 47 (1988).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Chatjigakis, A.K., Cardot, P.J.P., Coleman, A.W. et al. Retention properties of cyclodextrins and modified cyclodextrins in reversed phase HPLC. Chromatographia 36, 174–178 (1993). https://doi.org/10.1007/BF02263857
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02263857