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Studies on α-, β-, and γ-cyclodextrin inclusion complexes of isoquinoline alkaloids berberine, palmatine and coralyne

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Abstract

The complexation of three isoquinoline alkaloids berberine, palmatine and coralyne with α-, β-, and γ-CDs were studied by absorption, fluorescence, circular dichroism, NMR spectroscopy and microcalorimetric assay techniques. Their binding constant (K BH) values were determined by Benesi–Hildebrand equation. All the alkaloids formed 1:1 stoichiometry complexes with the cyclodextrins (CDs). The binding affinity is largest in β-CD followed by γ-, and α-CD for coralyne, followed by berberine and then palmatine. The thermodynamic parameters of the complexation were determined by calorimetry. The stoichiometry of complex formation and the variation of the apparent binding constant from spectroscopic studies were confirmed by calorimetry. The formation of the inclusion complexes was entropy driven in almost all the systems. Coralyne formed the strongest complex with all the CDs, followed by berberine and palmatine in that order. Coralyne-β-CD complex was studied through NMR, indicating more than one interaction mode.

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Acknowledgments

This work was supported by grants from the network Project GENCODE of the Council of Scientific and Industrial Research (CSIR), Govt. of India. Soumitra Hazra is a Junior Research Fellow of the CSIR awarded through the national eligibility test. Dr. Maidul Hossain was a Research Associate of the CSIR during the period of this work. The technical assistance of Mr. E. Padmanabhan with the NMR spectral measurements is gratefully acknowledged. The authors thank all the colleagues of the Biophysical Chemistry Laboratory for help and cooperation throughout the course of this work. Critical comments and the extensive helpful suggestions from the anonymous reviewers that enabled us to improve the quality of the manuscript considerably are highly appreciated.

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  1. Maidul Hossain

    Present address: Department of Chemistry, Vidyasagar University, Midnapore, 721102, West Bengal, India

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  1. Biophysical Chemistry Laboratory, Chemistry Division, CSIR-Indian Institute of Chemical Biology, Kolkata, 700032, India

    Soumitra Hazra, Maidul Hossain & Gopinatha Suresh Kumar

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10847_2013_301_MOESM1_ESM.tif

ESI Fig. S1 Changes in the absorption spectra of berberine (10 μM) (A and B), palmatine (10 μM) (C and D) and coralyne (1.0 μM) (E and F) with β-, and γ-CDs, respectively. In figure A (curves 1–5), C (curves 1–5) and E (curves 1–7) β-CD concentration varied from 0–100, 0–50 and 0–8 μM, respectively. In figure B (curves 1–4), D (curves 1–4) and F (curves 1–7) γ-CD concentration varied from 0–80, 0–40 and 0–8 μM, respectively. (TIFF 719 kb)

10847_2013_301_MOESM2_ESM.tif

ESI Fig. S2 Fluorescence spectral changes of berberine (10 μM) (A and B), palmatine (10 μM) (C and D) and coralyne (0.01 μM) (E and F) with α-, and γ-CDs, respectively. In figure A (curves 1–17), C (curves 1–9) and E (curves 1–9) β-CD concentration varied from 0–500, 0–240 and 0–30 μM, respectively. In figure B (curves 1–9), D (curves 1–8) and F (curves 1–9) γ-CD concentration vaired from 0–480, 0–40 and 0–35 μM, respectively. (TIFF 1098 kb)

10847_2013_301_MOESM3_ESM.tif

ESI Fig. S3 Job plots for the binding of (A) berberine, (B) palmatine and (C) coralyne to α- (circle), β- (square), γ- (triangle) CDs. The maximum concentration of berberine, palmatine and coralyne were 4.2, 3.9 and 2.0 μM, respectively. (TIFF 494 kb)

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Hazra, S., Hossain, M. & Kumar, G.S. Studies on α-, β-, and γ-cyclodextrin inclusion complexes of isoquinoline alkaloids berberine, palmatine and coralyne. J Incl Phenom Macrocycl Chem 78, 311–323 (2014). https://doi.org/10.1007/s10847-013-0301-6

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