Skip to main content
Log in

Complexation of 6-Deoxy-6-(aminoethyl)amino-β-cyclodextrin with Sodium Cholate and Sodium Deoxycholate

  • Published:
Journal of inclusion phenomena and macrocyclic chemistry Aims and scope Submit manuscript

Abstract

In order to study its guest binding and the inclusion phenomena, 6-deoxy-6-(aminoethyl)amino-β-cyclodextrin (βCDN) was synthesised and its binding properties examined. The complexation phenomena of sodium cholate (NaC) and sodium deoxycholate (NaDC) with βCDN has been monitored by the NMR method using 13C chemical shift data. The method of continuous variation ’“Job's method” has been used to determine the stoichiometry of these supramolecular complexes. The Job's plot confirms the 1 : 1 supramolecular complex for NaC: βCDN and the 1 : 2 supramolecular complex for NaDC: βCDN. The interaction of NaC and NaDC with βCDN has been obtained through two-dimensional Rotational Nuclear Overhauser Effect Spectroscopy (ROESY) NMR. Equilibrium constants were also obtained from 13C chemical shift data (C-1, C-3 & C-4) at different pH values (7, 9, & 11).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. J. Szejtli: ‘Comprehensive supramolecular chemistry', in J. Szejtli and T. Osa (eds.), Cyclodextrins, Vol. 3, Pergamon Press, U.K. (1996).

    Google Scholar 

  2. I. Bjorkhem: Sterols and Bile Acids (1985).

  3. X. Tan and S. Lindenbaum: Inter. J. Pharm. 74, 127 (1991).

    Google Scholar 

  4. P. Ramos, E. A. Parrilla, F. Meijide, and J. V. Tato: Conf. Proceed. of 9th Inter. Symp. on Cyclodextrins-Santiago de Compostela (1998).

  5. K. A. Connors: Binding Constants, The Measurement of Molecular Complex Stability, John Wiley and Sons, New York (1987).

    Google Scholar 

  6. N. Kobayashi, R. Saito, H. Hino, Y. Hino, A. Ueno, and T. Osa: J. Chem. Soc., Perkin Trans. 2 1031 (1983).

  7. K. A. Connors and J. M. Lipari: J. Pharm. Sci. 65, 379 (1976).

    Google Scholar 

  8. T. Cserhati, J. Szejtli, and T. Bojarski: Chromatographia 28, 455 (1989).

    Google Scholar 

  9. E. A. Lewis and L. D. Hansen: J. Chem. Soc., Perkin Trans. 2 2081 (1973).

  10. R. Palepu and V. C. Reinsborough: Can. J. Chem. 66, 325 (1988).

    Google Scholar 

  11. Y. Yamamoto, S. Shiraki, and Y. Kawamura: J. Chem. Soc., Perkin Trans. 2 2241 (1992).

    Google Scholar 

  12. O. Bekers, J. J. Kettenes-van den Bosch, S. P. van Helden, D. Seijkens, J. H. Beijnen, A. Bult, and W. J. M. Underberg: J. Incl. Phenom. Mol. Recognit. Chem. 11, 185 (1991).

    Google Scholar 

  13. D. M. Blow and A. Rich: J. Am. Chem. Soc. 82, 3566 (1960).

    Google Scholar 

  14. A. Jover, F. Meijide, E. R. Núñez, and J. V. Tato: Langmuir 13, 3590 (1997).

    Google Scholar 

  15. A. Jover, F. Meijide, E. R. Núñez, and J. V. Tato: Langmuir 14, 4359 (1998).

    Google Scholar 

  16. Y. Matsui and A. Okimoto: Bull. Chem. Soc. Jap. 51(10), 3030 (1978).

    Google Scholar 

  17. Y. Matsui, T. Yokoi, and K. Mochida: Chem. Lett. 1037 (1976).

  18. T. Nozaki, Y. Maeda, K. Ito, and H. Kitano: Macromolecules 28(2), 522 (1995).

    Google Scholar 

  19. V. M. S. Gil and N. C. Oliveira: J. Chem. Educ. 67, 473 (1990).

    Google Scholar 

  20. W. Likussar: Anal. Chem. 45(11), 1926 (1973).

    Google Scholar 

  21. B. L. May, S. D. Kean, C. J. Easton, and S. F. Lincoln: J. Chem. Soc. Perkin Trans. 1 3157 (1997).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Singh, A.P., Cabrer, P.R., Alvarez-Parrilla, E. et al. Complexation of 6-Deoxy-6-(aminoethyl)amino-β-cyclodextrin with Sodium Cholate and Sodium Deoxycholate. Journal of Inclusion Phenomena 35, 335–348 (1999). https://doi.org/10.1023/A:1008167520548

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1008167520548

Navigation