Chiral discrimination of sibutramine enantiomers by capillary electrophoresis and proton nuclear magnetic resonance spectroscopy

Archives of Pharmacal Research
Yong-Jae LeeKyeong Ho Kim

Abstract

Capillary electrophoresis (CE) and proton nuclear magnetic resonance spectroscopy ((1)H-NMR) have been used to discriminate the enantiomers of sibutramine using cyclodextrin derivatives. Possible correlation between CE and (1)H-NMR was examined. Good correlation between the (1)H-NMR shift non-equivalence data for sibutramine and the degree of enantioseparation in CE was observed. In CE study, a method of enantiomeric separation and quantitation of sibutramine was developed using enantiomeric standards. The method was based on the use of 50 mM of phosphate buffer of pH 3.0 with 10 mM of methyl-beta-cyclodextrin (M-β-CD). 0.05% of LOD, 0.2% of LOQ for S-sibutramine enantiomer was achieved, and the method was validated and applied to the quantitative determination of sibutramine enantiomers in commercial drugs. On a 600 MHz (1)H-NMR analysis, enantiomer signal separation of sibutramine was obtained by fast diastereomeric interaction with a chiral selector M-β-CD. For chiral separation and quantification, N-methyl proton peaks (at 2.18 ppm) were selected because of its being singlet and simple for understanding of diastereomeric interaction. Effects of temperature and concentration of chiral selector on enantiomer signal separation...Continue Reading

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Citations

May 3, 2014·Journal of Pharmaceutical and Biomedical Analysis·Zeineb AturkiSalvatore Fanali
Jun 20, 2016·Journal of Chromatography. a·Gerhard K E Scriba
Sep 30, 2014·Electrophoresis·Ioannis J StavrouConstantina P Kapnissi-Christodoulou
May 24, 2014·Electrophoresis·Pavel RezankaDavid Sýkora
Dec 21, 2012·Journal of Separation Science·Pavel Jáč, Gerhard K E Scriba
Aug 22, 2018·Pharmaceutical Development and Technology·Takayuki FuruishiEtsuo Yonemochi
Oct 2, 2019·Critical Reviews in Analytical Chemistry·Natalia CasadoMaría Luisa Marina
Aug 9, 2017·Journal of Physics. Condensed Matter : an Institute of Physics Journal·Paolo Lazzeretti
Aug 22, 2020·Journal of Chromatography. a·Ida FejősSzabolcs Béni

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