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Characterization of β-cyclodextrin inclusion complex with procaine hydrochloride by 1H NMR and ITC

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Abstract

The inclusion of local anesthetic drug procaine hydrochloride by β-cyclodextrin was investigated by 1D and 2D proton NMR spectroscopy and isothermal titration calorimetry (ITC) at 298 K. The stoichiometry of the complex was determinate by the method of continuous variation, using the chemical induced shift of both host and guest protons. The association constant K, of the obtained complex was calculated and found to be 293.17 M−1. Rotating frame NOE spectroscopy, was used to ascertain the solution geometry of the host–guest complex. The result reveals that the procaine molecule penetrates into the β-cyclodextrin cavity with the aromatic ring. The energetics of complexation process is investigated by ITC technique. The analysis indicates that the complexation of procaine by β-CD is an exothermic process and show that both enthalpy and entropy contribute to the binding process. The obtained value for the association constant is in good agreement with that obtained from NMR.

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Acknowledgments

This work was financially supported by UEFISCDI Romania, Project PCE-2011-3-0032.

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Authors and Affiliations

  1. National Institute for Research and Development of Isotopic and Molecular Technologies, 400293, Cluj-Napoca, Romania

    Adrian Pîrnău, Mihaela Mic, Mircea Bogdan & Ioan Turcu

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  1. Adrian Pîrnău
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  2. Mihaela Mic
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  3. Mircea Bogdan
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  4. Ioan Turcu
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Correspondence to Mihaela Mic.

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Pîrnău, A., Mic, M., Bogdan, M. et al. Characterization of β-cyclodextrin inclusion complex with procaine hydrochloride by 1H NMR and ITC. J Incl Phenom Macrocycl Chem 79, 283–289 (2014). https://doi.org/10.1007/s10847-013-0350-x

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  • DOI: https://doi.org/10.1007/s10847-013-0350-x

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