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Inclusion complexes with cyclodextrin and usnic acid

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Abstract

Molecular inclusion complexes of usnic acid (UA) with β-cyclodextrin (β-CD) and 2-hydroxypropyl β-cyclodextrin (HP β-CD) were prepared by the co-precipitation method in the solid state in the molar ratio of 1:1. Structural complexes characterization was based on different methods, FTIR, 1H NMR, XRD and DSC. Parallel to the complex by the above methods, corresponding physical mixtures of UA with cyclodextrins and complexing agents (β-CD, HP β-CD and UA) were analyzed. The results of DSC analysis showed that, at around 200 °C, the endothermal peak in the complexes with cyclodextrins originating from the UA melting has disappeared. Complex diffractogram patterns do not contain peaks characteristic for the pure UA. They are more appropriate to cyclodextrin diffractogram. This fact points to the molecular encapsulation of UA in the cyclodextrin cavity. Chemical shifts in 1H NMR spectra after the inclusion of UA into the cyclodextrin cavity, especially H-3 protons (0.0012 and 0.0102 ppm in the β-CD and HP β-CD, respectively) and H-5 and H-6 (0.0134 ppm) and hydrogen from CH3 (0.0073 ppm) HP β-CD also points to the formation of molecular inclusion complexes. The improved solubility of UA in water was achieved by molecular incapsulation. In the complex with β-CD the solubility is 0.3 mg/cm3, with HP β-CD 4.2 mg/cm3 while the uncomplexed UA solubility is 0.06 mg/cm3. The microbial activity of UA and both complexes was tested against eight bacteria and two fungi and during the test no reduced activity of UA in the complexes was observed.

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Acknowledgments

This work is a part of the research done within the project TR 34012. The authors would like to thank the Ministry of Education and Science, Republic of Serbia.

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Authors and Affiliations

  1. Faculty of Technology, University of Niš, Bulevar oslobodjenja 124, 16000, Leskovac, Republic of Serbia

    Vesna Nikolić, Mihajlo Stanković, Ljubiša Nikolić, Goran Nikolić & Snežana Ilić-Stojanović

  2. Faculty of Sciences, Department of Chemistry, University of Novi Sad, Trg Dositeja Obradovica 3, 21000, Novi Sad, Republic of Serbia

    Mirjana Popsavin

  3. Actavis Trading Ltd, Djordja Stanojevića 12, 11070, Belgrade, Republic of Serbia

    Saša Zlatković

  4. Department of Pharmacognosy, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11221, Belgrade, Republic of Serbia

    Tatjana Kundaković

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  1. Vesna Nikolić
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  2. Mihajlo Stanković
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Correspondence to Vesna Nikolić.

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Nikolić, V., Stanković, M., Nikolić, L. et al. Inclusion complexes with cyclodextrin and usnic acid. J Incl Phenom Macrocycl Chem 76, 173–182 (2013). https://doi.org/10.1007/s10847-012-0187-8

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  • DOI: https://doi.org/10.1007/s10847-012-0187-8

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