Separation of Tic-hydantoin enantiomers, potent sigma-1 agonists, by high performance liquid chromatography and capillary electrophoresis

J Chromatogr A. 2010 Jun 11;1217(24):3871-5. doi: 10.1016/j.chroma.2010.04.009. Epub 2010 Apr 24.

Abstract

Stereospecific separations of seven Tic-hydantoin sigma-1 agonists were performed by both HPLC method using derivatized cellulose and amylose chiral stationary phases and capillary electrophoresis (CE) method using neutral and anionic cyclodextrins added in the background electrolyte (BGE). An optimal baseline separation (R(s)>3.3 with analysis times<25min) was readily obtained with all silica-based celluloses and amyloses using a normal-phase methodology. CE was used as an alternative technique to HPLC for the Tic-hydantoin derivatives separation. The enantiomers were fully resolved with highly sulfated beta-cyclodextrins at pH 2.5 (R(s)>1.5 with analysis times <11min). Both methods were validated in terms of linearity, detection and quantification limits. They were used to check the enantiomeric purity of the enantiomers.

MeSH terms

  • Chromatography, High Pressure Liquid / methods*
  • Cyclodextrins / isolation & purification
  • Electrophoresis, Capillary / methods*
  • Hydantoins / chemistry*
  • Hydantoins / metabolism
  • Linear Models
  • Receptors, sigma / agonists
  • Receptors, sigma / metabolism
  • Reproducibility of Results
  • Sensitivity and Specificity
  • Sigma-1 Receptor
  • Stereoisomerism
  • Tetrahydroisoquinolines / chemistry*
  • Tetrahydroisoquinolines / metabolism

Substances

  • Cyclodextrins
  • Hydantoins
  • Receptors, sigma
  • Tetrahydroisoquinolines