Synthesis and application of tetramethylammonium-carboxymethylated-β-cyclodextrin: A novel ionic liquid in capillary electrophoresis enantioseparation

J Pharm Biomed Anal. 2020 Feb 20:180:113030. doi: 10.1016/j.jpba.2019.113030. Epub 2019 Dec 5.

Abstract

In this study, a carboxymethylated-β-cyclodextrin-based chiral ionic liquid (CIL), tetramethylammonium-carboxymethylated-β-cyclodextrin (TMA-CM-β-CD) was successfully designed and synthesized. This cyclodextrin-based ionic liquids (ILs) was used as the sole chiral selector in capillary electrophoresis, and it is very interesting to find that the chiral separation capability can be remarkably improved when a conventional cyclodextrin chiral selector evolved into an IL chiral selector. The ionic liquid showed satisfactory separation performance towards twelve tested drugs. A series of parameters affecting the enantioseparation, such as the type and proportion of organic modifier, buffer pH, chiral selector concentration, as well as applied voltage were systematically investigated. Additionally, the molecular docking program Autodock was applied to further demonstrate the mechanism of chiral recognition and the enhanced enantioselectivity of TMA-CM-β-CD, which kept in agreement with our experimental results.

Keywords: Capillary electrophoresis; Chiral selector; Ionic liquids; Molecular docking.

MeSH terms

  • Electrophoresis, Capillary
  • Ionic Liquids / chemistry*
  • Molecular Docking Simulation
  • Quaternary Ammonium Compounds / chemistry*
  • Solvents / chemistry
  • Stereoisomerism
  • beta-Cyclodextrins / chemistry*

Substances

  • Ionic Liquids
  • Quaternary Ammonium Compounds
  • Solvents
  • beta-Cyclodextrins
  • tetramethylammonium