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Enantiomeric Separation of Two Antiparkinsonian Drugs by Electrokinetic Chromatography Using Dextran Sulfate

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Abstract

Anionic polysaccharide dextran sulfate (DxS) was successfully employed as chiral selector for the enantioseparation of two antiparkinsonian drugs, including rotigotine and trihexyphenidyl (THP), by electrokinetic chromatography (EKC). The enantioseparation was performed under normal and reversed polarity modes and reversed enantiomer migration order was achieved under two modes. The parameters affecting the chiral separation, such as buffer pH, DxS concentration, organic additive, and temperature were investigated and optimized. Reversed polarity mode provided better separation for the two drugs. The optimized conditions for the enantioseparation under reversed polarity mode were 2.0% (w/v) DxS, 10 mM phosphate buffer, pH 2.5 with an applied voltage of −30 kV at 25 °C. Direct UV detection was performed at 200 nm. Under the optimal conditions, rotigotine and THP enantiomers were enantioresolved in 40 min with the resolution of 2.0 and 5.8, respectively. The analytes could be enantioseparated using DxS of molecular mass 1,000,000 or 500,000. It was inferred that the electrostatic, hydrophobic, and steric interactions may be involved in the chiral separation mechanism in this study.

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Acknowledgments

The authors would like to thank the National Natural Science Foundation of China (Grant Nos. 90813015, 20575008).

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Authors and Affiliations

  1. State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, 100029, Beijing, China

    Bao-Lin Chu & Zhihua Wang

  2. The Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, 100084, Beijing, China

    Bao-Lin Chu, Qinzhong Feng & Jin-Ming Lin

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  1. Bao-Lin Chu
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  2. Qinzhong Feng
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  3. Zhihua Wang
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  4. Jin-Ming Lin
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Correspondence to Jin-Ming Lin.

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Chu, BL., Feng, Q., Wang, Z. et al. Enantiomeric Separation of Two Antiparkinsonian Drugs by Electrokinetic Chromatography Using Dextran Sulfate. Chroma 70, 817–824 (2009). https://doi.org/10.1365/s10337-009-1232-7

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