Abstract
α-Cyclodextrin (α-CD) has specific interactions with a number of important molecules including neurotoxins, pesticides, and hydrophobic drugs. Here, we describe the kinetics of a competitive inhibition of the interaction of α-CD with chromogenic polydiacetylene (PDA) liposomes. The competitive inhibition of α-CD with chromogenic PDA liposomes has already been used for sensing and detection purposes. Here we show that this mechanism can be successfully applied to characterize the reaction kinetics of α-CD with optically inactive compounds such as paraoxon neurotoxins via simple colorimetric changes. This method would enable easy characterisation of the interactions of α-CD when used as a drug delivery system or for drug solubilisation.
Graphical Abstract
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Eftink, M.R., Andy, M.L., Bystrom, K., Perlmutter, H.D., Kristol, D.S.: Cyclodextrin inclusion complexes: studies of the variation in the size of alicyclic guests. J. Am. Chem. Soc. 111, 6765–6772 (1989)
Spencer, J.N., De Garmo, J., Paul, I.M., He, Q., Ke, X., Wu, Z., Yoder, C.H., Chen, S., Mihalick, J.E.: Inclusion complexes of alcohols with α-cyclodextrin. J. Solut. Chem. 24, 601–609 (1995)
Konkena, B., Vasudevan, S.: Resonance Raman detection and estimation in the aqueous phase using water dispersible cyclodextrin: reduced-graphene oxide sheets. Anal. Chem. 85, 5114–5119 (2013)
Chen, X., Cheng, X., Gooding, J.J.: Detection of trace nitroaromatic isomers using indium tin oxide electrodes modified using β-cyclodextrin and silver nanoparticles. Anal. Chem. 84, 8557–8563 (2012)
Wang, L., Lei, J., Ma, R., Ju, H.: Host–guest interaction of adamantine with a β-cyclodextrin-functionalized AuPd bimetallic nanoprobe for ultrasensitive electrochemical immunoassay of small molecules. Anal. Chem. 85, 6505–6510 (2013)
Ma, C., Bian, T., Yang, S., Liu, C., Zhang, T., Yang, J., Li, Y., Li, J., Yang, R., Tan, W.: Fabrication of versatile cyclodextrin-functionalized upconversion luminescence nanoplatform for biomedical imaging. Anal. Chem. 86, 6508–6515 (2014)
Anekthirakun, P., Sukwattanasinitt, M., Tuntulani, T., Imyim, A.: Naked eye screening of 11 phenolic compounds and colorimetric determination using polydiacetylene vesicles with α-cyclodextrin. Spectrochim. Acta Part A 111, 91–96 (2013)
Del Valle, E.M.M.: Cyclodextrins and their uses: a review. Process Biochem. 39, 1033–1046 (2004)
Vyas, A., Saraf, S., Saraf, S.: Cyclodextrin based novel drug delivery systems. J. Incl. Phenom. Macrocycl. Chem. 62, 23–42 (2008)
Chen, X., Hong, L., You, X., Wang, Y., Zou, G., Su, W., Zhang, Q.: Photo-controlled molecular recognition of [small alpha]-cyclodextrin with azobenzene containing polydiacetylene vesicles. Chem. Commun. 11, 1356–1358 (2009)
Plätzer, M., Schwarz, M.A., Neubert, R.H.H.: Determination of formation constants of cyclodextrin inclusion complexes using affinity capillary electrophoresis. J. Microcolumn Sep. 11, 215–222 (1999)
Herrmann, W., Keller, B., Wenz, G.: Kinetics and thermodynamics of the inclusion of ionene-6,10 in α-cyclodextrin in an aqueous solution. Macromolecules 30, 4966–4972 (1997)
Jones, C.J., Larive, C.K.: Microcoil NMR study of the interactions between doxepin, β-cyclodextrin, and acetate during capillary isotachophoresis. Anal. Chem. 84, 7099–7106 (2012)
Kahle, C., Holzgrabe, U.: Determination of binding constants of cyclodextrin inclusion complexes with amino acids and dipeptides by potentiometric titration. Chirality 16, 509–515 (2004)
Dotsikas, Y., Loukas, Y.L.: Efficient determination and evaluation of model cyclodextrin complex binding constants by electrospray mass spectrometry. J. Am. Soc. Mass Spectrom. 14, 1123–1129 (2003)
Rajendiran, N., Venkatesh, G., Sankaranarayanan, R.K.: Encapsulation of thiazolyazoresorcinol and thiazolyazocresol dyes with α- and β-cyclodextrin cavities: spectral and molecular modeling studies. J. Mol. Struct. 1072, 242–252 (2014)
Ahn, D.J., Lee, S., Kim, J.-M.: Rational design of conjugated polymer supramolecules with tunable colorimetric responses. Adv. Funct. Mater. 19, 1483–1496 (2009)
Carpick, R.W., Sasaki, D.Y., Marcus, M.S., Eriksson, M.A., Burns, A.R.: Polydiacetylene films: a review of recent investigations into chromogenic transitions and nanomechanical properties. J. Phys. 16, R679 (2004)
Kim, J.-M., Lee, J.-S., Lee, J.-S., Woo, S.-Y., Ahn, D.J.: Unique effects of cyclodextrins on the formation and colorimetric transition of polydiacetylene vesicles. Macromol. Chem. Phys. 206, 2299–2306 (2005)
Soni, S.-D., Bhonsle, J.B., Garcia, G.E.: Biophysical aspects of cyclodextrin interaction with paraoxon. Magn. Reson. Chem. 52, 111–114 (2014)
Acknowledgments
This work was supported by the University of Minnesota MnDrive Global Food Venture and the Undergraduate Research Opportunities Program.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Brockgreitens, J., Ahmed, S. & Abbas, A. Kinetic analysis of α-cyclodextrin interactions using polydiacetylene liposomes. J Incl Phenom Macrocycl Chem 81, 423–427 (2015). https://doi.org/10.1007/s10847-014-0470-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10847-014-0470-y