Capillary electrophoretic separation and computational modeling of inclusion complexes of β-cyclodextrin and 18-crown-6 ether with primaquine and quinocide

Abdalla A. Elbashir, Fakhr Eldin Osman Suliman, Bahruddin Saad, Hassan Y. Aboul-Enein

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

The antimalarial drug primaquine (PQ) and its contaminant, the positional isomer quinocide (QC) have been successfully separated using capillary electrophoresis with either β-cyclodextrin (β-CD) or 18-crown-6 ether (18C6) as chiral mobile phase additive. The interactions of the drugs with cyclodextrins and 18C6 were studied by the semiempirical method (Parametric Model 3) PM3. Theoretical calculations for the inclusion complexes of PQ and QC with α-CD, β-CD and 18C6 were performed. Data from the theoretical calculations are correlated and discussed with respect to the electrophoretic migration behavior. More stable complexes are predicted for the PQ-β-CD and PQ-18C6 complexes. The coelution of PQ and QC when α-CD was used as buffer additive can be explained by their comparable stabilities of the inclusion complex formed, while significant differences in the complexation stabilities of the drugs with β-CD is responsible for their separation. The stronger hydrogen bonding in PQ-18C6 system is responsible for the separation between PQ and QC when 18C6 was used as chiral mobile phase additive.

Original languageEnglish
Pages (from-to)393-398
Number of pages6
JournalBiomedical Chromatography
Volume24
Issue number4
DOIs
Publication statusPublished - 2010

Fingerprint

Primaquine
Crown Ethers
Cyclodextrins
Ether
Drug Stability
Capillary electrophoresis
Antimalarials
Capillary Electrophoresis
Hydrogen Bonding
18-crown-6
quinocide
Complexation
Drug Interactions
Isomers
Pharmaceutical Preparations
Hydrogen bonds
Buffers
Impurities

Keywords

  • 18-crown-6
  • Capillary electrophoresis
  • Inclusion complexes
  • PM3
  • β-cyclodextrin

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Pharmacology
  • Medicine(all)

Cite this

Capillary electrophoretic separation and computational modeling of inclusion complexes of β-cyclodextrin and 18-crown-6 ether with primaquine and quinocide. / Elbashir, Abdalla A.; Suliman, Fakhr Eldin Osman; Saad, Bahruddin; Aboul-Enein, Hassan Y.

In: Biomedical Chromatography, Vol. 24, No. 4, 2010, p. 393-398.

Research output: Contribution to journalArticle

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