A study of the interaction between enantiomers of zolmitriptan and hydroxypropyl-beta-cyclodextrin by capillary electrophoresis

Anal Bioanal Chem. 2009 Jan;393(1):313-20. doi: 10.1007/s00216-008-2446-5. Epub 2008 Oct 19.

Abstract

The enantioresolution of zolmitriptan was performed using cyclodextrin (CD)-modified capillary zone electrophoresis (CZE) with hydroxypropyl-beta-CD (HP-beta-CD) as the chiral selector. The influence of experimental conditions on the enantioseparation of zolmitriptan, such as pH, temperature, applied voltage, and concentrations of running electrolyte and CD, was systematically investigated, obtaining a baseline separation of two enantiomers by the use of a 25 mM sodium dihydrogen phosphate (SDPH) running electrolyte (pH 2.4) containing 30 mM HP-beta-CD at 15 degrees C. Binding constants for each enantiomer-HP-beta-CD pair at different temperatures, as well as thermodynamic parameters for binding, were calculated. A nonlinear van't Hoff plot was obtained, indicating that the thermodynamic parameters of complexation were temperature-dependent for zolmitriptan enantiomers. The significant contribution of the enthalpy difference to the Gibbs free energy change suggested a stereomeric barrier mechanism for chiral recognition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Hydroxypropyl-beta-cyclodextrin
  • Electrochemistry
  • Electrolytes / chemistry
  • Electrophoresis, Capillary
  • Hydrogen-Ion Concentration
  • Molecular Conformation
  • Oxazolidinones / analysis*
  • Oxazolidinones / chemistry*
  • Phosphoric Acids / chemistry
  • Stereoisomerism
  • Temperature
  • Thermodynamics
  • Tryptamines / analysis*
  • Tryptamines / chemistry*
  • beta-Cyclodextrins / analysis*
  • beta-Cyclodextrins / chemistry*

Substances

  • Electrolytes
  • Oxazolidinones
  • Phosphoric Acids
  • Tryptamines
  • beta-Cyclodextrins
  • 2-Hydroxypropyl-beta-cyclodextrin
  • zolmitriptan
  • phosphoric acid