Comparative analysis of the full set of methylated β-cyclodextrins as chiral selectors in capillary electrophoresis

Erzsébet Varga, Gábor Benkovics, András Darcsi, Bianka Várnai, Tamás Sohajda, Milo Malanga, S. Béni

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The chiral separation ability of the full library of methylated-β-cyclodextrins towards pharmacologically significant racemic drugs including basic compounds was studied by chiral CE. The syntheses of all the methylated, single isomer β-cyclodextrins were revised and optimized and the aqueous solubility of the derivatives was unambiguously established. The three most relevant commercially available methylated isomeric mixtures were also included in the screening, so a total of ten various methylated CDs were investigated. The effects of the selector concentration on the enantiorecognition properties at acidic pH were investigated. Among the dimethylated β-cyclodextrins, the heptakis (2,6-di-O-methyl)-β-cyclodextrin isomer (2,6-DIMEB) resulted to be the most versatile chiral selector. Terbutaline was selected as a model compound for the in-depth investigation of host-guest enantiodiscrimination ability. The association constants between the two terbutaline enantiomers and 2,6-DIMEB were determined in order to support that the enantioseparation is driven by differences is host-guest binding. The migration order of the enantiomers was confirmed by performing spiking experiments with the pure enantiomers. 1D and 2D NMR spectroscopy was applied to the 2,3-, and 2,6-DIMEB/terbutaline systems to rationalize at molecular level the different enantioseparation ability of the dimethylated β-cyclodextrin selectors.

Original languageEnglish
JournalElectrophoresis
DOIs
Publication statusPublished - Jan 1 2019

Fingerprint

Capillary electrophoresis
Cyclodextrins
Capillary Electrophoresis
Terbutaline
Enantiomers
Isomers
Solubility
Nuclear magnetic resonance spectroscopy
Libraries
Screening
Magnetic Resonance Spectroscopy
Association reactions
Derivatives
Pharmaceutical Preparations
Experiments

Keywords

  • Crystalline methylated cyclodextrin
  • Dimethylated cyclodextrins
  • Enantioseparation
  • Randomly methylated cyclodextrin
  • Single isomer

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry

Cite this

Comparative analysis of the full set of methylated β-cyclodextrins as chiral selectors in capillary electrophoresis. / Varga, Erzsébet; Benkovics, Gábor; Darcsi, András; Várnai, Bianka; Sohajda, Tamás; Malanga, Milo; Béni, S.

In: Electrophoresis, 01.01.2019.

Research output: Contribution to journalArticle

Varga, Erzsébet ; Benkovics, Gábor ; Darcsi, András ; Várnai, Bianka ; Sohajda, Tamás ; Malanga, Milo ; Béni, S. / Comparative analysis of the full set of methylated β-cyclodextrins as chiral selectors in capillary electrophoresis. In: Electrophoresis. 2019.
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