Separation of cis-β-lactam enantiomers by capillary electrophoresis using cyclodextrin derivatives

Krisztina Németh, Erzsébet Varga, Róbert Iványi, Julianna Szemán, Júlia Visy, László Jicsinszky, Lajos Szente, Eniko Forró, Ferenc Fülöp, Antal Péter, Miklós Simonyi

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Chiral separation of 19 pairs of cis-β-lactam (BL) stereoisomers of pharmacological importance was examined by capillary electrophoresis using cyclodextrin (CD) derivatives. In order to select the most effective conditions separating the highest number of stereoisomers of BLs, single carboxymethyl α-, β- and γ-, as well as sulfobutyl β-CD derivatives were applied. Additionally, carboxymethyl and sulfobutyl β-CD derivatives complemented with neutral β-CD derivatives as dual CD systems were tested. Both the composition and concentration of applied selectors and the pH of background electrolyte were selected. In single systems the structural characteristics of BLs and the complex forming affinity were correlated. Most BLs provided optimal complexation with β-CD derivatives. In conclusion, the efficiency of combining sulfobutyl-β-CD and permethylated β-CD was superior to other single and dual CD systems applied. This method successfully separated each pair of stereoisomers investigated.

Original languageEnglish
Pages (from-to)382-388
Number of pages7
JournalJournal of Pharmaceutical and Biomedical Analysis
Volume53
Issue number3
DOIs
Publication statusPublished - Nov 1 2010

Keywords

  • Apparent complex stability constant
  • Capillary electrophoresis
  • Chiral separation of β-lactams
  • Dual cyclodextrin system
  • Reversed order of enantiomer migration

ASJC Scopus subject areas

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

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