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A comparative study of inclusion complexes of flunarizine with alpha (α-CD) and beta-cyclodextrin (β-CD)

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Abstract

A detailed NMR (1H, COSY, and ROESY) spectroscopic study of complexation of Flunarazine (FL) with α- and β-CD was carried out. 1H NMR titration studies confirmed the formation of FL/α-CD and FL/β-CD complexes as evidenced by chemical shift variations of the proton resonances of both the CDs and FL. The stoichiometry of the complexes was determined to be 1:2 (FL/α-CD) and 1:1 (FL/β-CD) and overall binding constants were also calculated. It was confirmed with the help of ROESY spectral data that only one of the F-substituted aromatic ring and phenyl ring penetrate the α-CD cavity while both F-substituted aromatic rings as well as phenyl ring penetrates the β-CD cavity during complexation. The binding modes of FL/CD cavity interactions derived from ROESY experimental data show that the resulting complex of FL with β-CD possesses better induced fit interaction as compared to α-CD, which is responsible for the enhanced molecular stability with β-CD in comparison to α-CD. The mode of penetration of guest into the CD cavity and structures of the complexes has been established.

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Acknowledgements

Flunarizine and β-cyclodextrin were very kindly provided by Dr. Reddy’s laboratory India, and Geertrui Haest, Cerestar Cargill, Belgium, respectively. We are highly grateful to Prof. S. W. Homans, Department of Biochemistry and Molecular Biology, University of Leeds, UK and Dr. P. De Waard, Department of Biophysics, Dreijenlaan, The Netherlands, for their help in obtaining some of the NMR data.

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  1. Department of Chemistry, IET, Mangalayatan University, Beswan, Aligarh, India

    Arti Maheshwari

  2. Department of Physics, IET, Mangalayatan University, Beswan, Aligarh, India

    Deepak Sharma

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  1. Arti Maheshwari
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  2. Deepak Sharma
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Correspondence to Arti Maheshwari.

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Maheshwari, A., Sharma, D. A comparative study of inclusion complexes of flunarizine with alpha (α-CD) and beta-cyclodextrin (β-CD). J Incl Phenom Macrocycl Chem 68, 453–459 (2010). https://doi.org/10.1007/s10847-010-9809-1

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