Enantio-resolution of some chiral sulfoxide drugs on amylose and cellulose-based stationary phases: Elution order, absolute configuration and chiral mechanism determination

Khadidja Addadi, Khaled Sekkoum, Nasser Belboukhari, Zeid A. ALOthman, Ahmed M. Aljuwayid, Mika Sillanpää, Imran Ali

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The enantio-separation of three chiral sulfoxide drugs (omeprazole, pantoprazole, and lansoprazole) was achieved on Chiralpak® AS-3R column with acetonitrile‐water (65:35) at 0.5 mL/min flow and 280 nm detection within 7 min. Chiral separation was validated properly with 9.70–14.16 and 29.39–42.91 µg.mL−1 as LOD and LOQ. The thermodynamics parameters were in the range of (-0.51 to −1,288) kJ mol−1K−1 (ΔG). These values confirmed chiral separation as spontaneous and thermodynamically stable. Enantiomer elution order determined on Chiralpak® IA with ethanol-hexane (95:5)at 1.0 mL/min flow at 221, 254, 270, 280,301, and 330 nm wavelengths confirmed first elution od S-enantiomer followed by R-enantiomer. This observation was also confirmed by theoretical simulations of electronic circular dichroism (ECD) calculation. The docking study was used to explain the chiral resolution of the reported drugs. As a result, a simple, fast, reliable and spontaneous and thermodynamically stable HPLC method was developed for the separation and determination of enantiomer elution order of the reported chiral sulfoxide drugs.

Original languageEnglish
Article number109019
JournalMicrochemical Journal
Volume193
DOIs
Publication statusPublished - Oct 2023
Externally publishedYes

Keywords

  • Chiral sulfoxide drugs
  • Elution order
  • Enantio-separation
  • Molecular docking
  • Polysaccharide stationary phase CSP

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy

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