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Nanodimer cyclodextrin ligands with high affinity to steroids

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Abstract

Molecular-imprinting by cross-linking of ligands of β-cyclodextrin (CD) complex with steroids has been developed for the synthesis of tailor-made CD dimer. Steroids of androstane (9α-hydroxy-androst-4-en-3,17-dione, androst-4-en-3,17-dione, androsta-1,4-dien-3,17-dione (ADD)) and pregnane (hydrocortisone, 6-methyl-hydrocortisone, 20-hydroxymethylpregna-1,4-diene-3-one (HMPD)) series were used as template molecules. For imprinting procedure, crystalline β-CD complexes of exact stoichiometry (β-CD:steroid template = 2:1) were synthesized following by toluene 2,4-diisocyanate (TDI) cross-linking. The attempts to produce CD dimer for steroid without hydrophobic side chain failed, while tailor-made CD dimer has been obtained using HMPD as a template. The dimer was characterized by 1H NMR and mass-spectrometry. The complex stability constant (KS) towards HMPD template exceeded 107 M−1. The KS of CD dimer with ADD exceeded the corresponded value of TDI-modified CD monomer by more than an order of magnitude. The dimer was applied for quantitative extraction of ADD from aqueous solution using dialysis membranes impermeable for CD. The value of KS for ADD estimated from balanced concentrations of dialysis data corresponded to that calculated by nonlinear spectrometric method.

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Acknowledgments

Authors thank Dr. A. D. Averin in Moscow State University for 1H NMR experiments and helpful discussion.

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Authors and Affiliations

  1. G.K. Skryabin Institute of Biochemistry & Physiology of Microorganisms, Pushchino, Russia

    Sergey Khomutov & Marina V. Donova

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  1. Sergey Khomutov
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  2. Marina V. Donova
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Correspondence to Sergey Khomutov.

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Khomutov, S., Donova, M.V. Nanodimer cyclodextrin ligands with high affinity to steroids. J Incl Phenom Macrocycl Chem 70, 353–357 (2011). https://doi.org/10.1007/s10847-010-9896-z

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  • DOI: https://doi.org/10.1007/s10847-010-9896-z

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