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Investigation of indole chalcones encapsulation in β-cyclodextrin: determination of stoichiometry, binding constants and thermodynamic parameters

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Abstract

The study focuses on the formation of inclusion complexes of indole chalcone (IC) derivatives with β-cyclodextrin (β-CD), which involves absorption and steady state fluorescence spectroscopies. The formation of inclusion complexes is validated by increase in their absorbance and fluorescence intensity as well as the blue shift with increase in the concentration of β-CD in the aqueous solution. The stoichiometries and binding constants (Kin) of these complexes have been investigated by monitoring their absorbance and fluorescence spectral profiles. The data are analyzed by Benesi–Hildebrand plots as well as Job’s method, which indicate 1:1 stoichiometry of IC:β-CD complexes. Fluorescence measurements are also used to investigate the effect of temperature on the stability of inclusion complexes. Stability of IC:β-CD complexes is significantly affected with variation in substituents on the phenyl ring and temperature. It is observed that the stability of the inclusion complex decreases with increase in temperature; Kin(293 K) > Kin(298 K) > Kin(308 K) > Kin(318 K). All the experimental results and the geometrical data obtained using PM3 semiempirical method illustrate the partial inclusion of IC derivatives from the phenyl ring side in β-CD cavity. The binding process of IC derivatives with β-CD is found to be exothermic in nature and seems to be controlled by electrostatic and hydrophobic forces. The binding free energies calculated using semiemprical PM3 method for IC:β-CD complexes are found to be in the order: I < OH–I < Me–I < OMe–I < NH2–I, which largely supports the findings based on the experimental binding constants.

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Acknowledgements

The financial support from University of Delhi under the Scheme “To strengthen Research and Development Doctoral Research Program” is gratefully acknowledged. Manju K. Saroj is thankful to the University Grants Commission, New Delhi for the financial assistance.

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  1. Sapan K. Jain

    Present address: Department of Chemistry, Jamia Millia Islamia, Delhi, 110025, India

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  1. Department of Chemistry, University of Delhi, Delhi, 110007, India

    Manju K. Saroj, Ritu Payal, Sapan K. Jain, Neera Sharma & Ramesh C. Rastogi

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Correspondence to Ramesh C. Rastogi.

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Saroj, M.K., Payal, R., Jain, S.K. et al. Investigation of indole chalcones encapsulation in β-cyclodextrin: determination of stoichiometry, binding constants and thermodynamic parameters. J Incl Phenom Macrocycl Chem 90, 305–320 (2018). https://doi.org/10.1007/s10847-018-0782-4

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