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Novel Vinylpyridine Based Cationic MIP Monoliths for Enantiomer Separation in CEC

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Abstract

Cationic vinylpyridine based molecularly imprinted polymer monoliths were, for the first time, applied to enantiomer separation using capillary electrochromatography. In order to map the synthesis conditions under which superporous monoliths are obtained, capillary columns were prepared by an in situ polymerization technique using varying monomer and porogen compositions. Both electrolyte pH and percentage of the organic modifier acetonitrile were found to affect the electrochromatographic behaviour on such columns. An interesting observation is that the electroosmotic flow changed direction from cathodic at high pH to anodic at low pH of the electrolyte, opening up the opportunity to manipulate the flow. This is attributed to the vinylpyridine based MIP becomes protonated and positively charged at low pH, whereas it is uncharged at high pH where instead negatively charged silanol groups drive the electroosmotic flow. Improved enantiomer resolution, as well as increased retention, was observed when the concentration of acetonitrile in the electrolyte decreased, indicating a significant element of hydrophobic effects in the molecular recognition of the imprinted enantiomer. Enantiomer separation of the non-steroidal anti-inflammatory drug ibuprofen was studied and efficiencies as high as 30,000 plates per meter with an asymmetry factor below 4 were obtained for the last eluting imprinted enantiomer. These values are better than that obtained generally using MIP based chromatography.

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Acknowledgments

We gratefully acknowledge the financial support from the Carl Trygger foundation, The Swedish Fund for Research without Animal Experiments, Kungliga Fysiografiska Sällskapet i Lund, the Swedish research Council (VR) (Grant No 40455901 to SN), the Crafoord Foundation and AstraZeneca.

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  1. Peter Spégel

    Present address: Unit of Molecular Metabolism, Department of Clinical Sciences in Malmö, Lund University Diabetes Center, 205 02, Malmö, Sweden

Authors and Affiliations

  1. Analytical Chemistry, Lund Institute of Technology, Lund University, P.O. Box 124, 221 00, Lund, Sweden

    Peter Spégel

  2. Analytical Development, AstraZeneca R&D Mölndal, 431 83, Mölndal, Sweden

    Leif Schweitz

  3. Disease Biology, AstraZeneca R&D Södertälje, 151 85, Södertälje, Sweden

    Lars I. Andersson

  4. Pure and Applied Biochemistry, Lund Institute of Technology, Lund University, P.O. Box 124, 221 00, Lund, Sweden

    Staffan Nilsson

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  1. Peter Spégel
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  4. Staffan Nilsson
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Correspondence to Peter Spégel.

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Spégel, P., Schweitz, L., Andersson, L.I. et al. Novel Vinylpyridine Based Cationic MIP Monoliths for Enantiomer Separation in CEC. Chroma 69, 277–285 (2009). https://doi.org/10.1365/s10337-008-0911-0

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