Chromatographia

, Volume 76, Issue 21–22, pp 1449–1458 | Cite as

Enantioseparation of Chiral Antimycotic Drugs by HPLC with Polysaccharide-Based Chiral Columns and Polar Organic Mobile Phases with Emphasis on Enantiomer Elution Order

  • Antonina Mskhiladze
  • Marina Karchkhadze
  • Alexandre Dadianidze
  • Salvatore Fanali
  • Tivadar Farkas
  • Bezhan Chankvetadze
Original
First Online:
Received:
Revised:
Accepted:

Abstract

The separation of enantiomers of 10 chiral antimycotic drugs was studied on polysaccharide-based chiral columns with polar organic mobile phases. The emphasis was placed on some interesting examples of enantiomer elution order reversal observed depending on the chemistry of the chiral selector, separation temperature, major component, as well as the minor additive in the mobile phase. In particular, it was found that the elution order of enantiomers of chiral drug terconazole was opposite on cellulose- and amylose-based columns with the same pendant group. The affinity pattern of enantiomers of another chiral drug bifonazole was opposite towards to two amylose-based chiral selectors with different pendant groups. The affinity pattern of terconazole enantiomers also changed on some columns when the alcohol-based mobile phase was replaced with acetonitrile. An interesting effect of the minor acidic (formic acid) additives to the mobile phase on the affinity pattern of terconazole enantiomers was observed on Cellulose-2 and Cellulose-4 columns. In addition, a reversal of elution order of bifonazole enantiomers was observed on Amylose-2 column by variation of a separation temperature.

Keywords

Column liquid chromatography Polysaccharide-based chiral columns Separation of enantiomers Enantiomer elution order Chiral antimycotic drugs 
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Copyright information

© Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  • Antonina Mskhiladze
    • 1
  • Marina Karchkhadze
    • 2
  • Alexandre Dadianidze
    • 2
  • Salvatore Fanali
    • 3
  • Tivadar Farkas
    • 4
  • Bezhan Chankvetadze
    • 2
  1. 1.Faculty of Natural Sciences and HealthcareSokhumi State UniversityTbilisiGeorgia
  2. 2.Institute of Physical and Analytical Chemistry, School of Exact and Natural SciencesTbilisi State UniversityTbilisiGeorgia
  3. 3.Institute of Chemical Methodologies, Italian National Research CouncilMonterotondoItaly
  4. 4.Phenomenex IncTorranceUSA

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