Enantiomers of triclabendazole sulfoxide: Analytical and semipreparative HPLC separation, absolute configuration assignment, and transformation into sodium salt

Rosella Ferretti, Simone Carradori, Paolo Guglielmi, Marco Pierini, Adriano Casulli, Roberto Cirilli

Research output: Contribution to journalArticlepeer-review

Abstract

Direct HPLC separation of the enantiomers of triclabendazole sulfoxide (TCBZ-SO), which is the main metabolite of the anthelmintic drug triclabendazole, was carried out using the polysaccharide-based Chiralpak AS-H and Chiralpak IF-3 chiral stationary phases (CSPs). The chromatographic behaviour of both CSPs was evaluated and compared using normal-phase and reversed-phase eluents at different column temperatures. The eluent mixture of n-hexane-2-propanol-trifluoroacetic acid 70:30:0.1 (v/v/v) and a column temperature of 40 °C were identified as the best operational conditions to carry out semipreparative enantioseparations on a 1-cm I.D. AS-H column. Under these conditions, 12.5 mg of racemic sample were resolved in a single chromatographic run within 15 min. Comparison of calculated and experimental chiroptical properties provided the absolute configuration assignment at the sulfur atom. The salification of the isolated enantiomers of TCBZ-SO by reaction with sodium hydroxide solution produced water-soluble Na salts which are potentially useful in the development of new anthelmintic enantiomerically pure formulations.

Original languageEnglish
Pages (from-to)38-44
Number of pages7
JournalJournal of Pharmaceutical and Biomedical Analysis
Volume140
DOIs
Publication statusPublished - Jun 5 2017

Keywords

  • Absolute configuration assignment
  • Chiralpak AS-H
  • Chiralpak IF-3
  • Enantiomers
  • Parasites
  • Triclabendazole sulfoxide

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmaceutical Science
  • Drug Discovery
  • Spectroscopy
  • Clinical Biochemistry

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