Separation and characterization of modified pregabalins in terms of cyclodextrin complexation, using capillary electrophoresis and nuclear magnetic resonance

Journal of Pharmaceutical and Biomedical Analysis
Szabolcs BéniBéla Noszál

Abstract

The (S)-(+)-isomer of 3-isobutyl-GABA (pregabalin), the blockbuster drug in the treatment of neuropathic pain has been separated from its R isomer by cyclodextrin modified capillary zone electrophoresis (CZE) using uncoated fused-silica capillary. Derivatization of the single isomer and the racemate with tosyl- and dansyl-chloride was carried out to introduce strong UV chromophores of different size. CE-pH titrations were performed to determine the dissociation constants for both derivatives. 30 cyclodextrin (CD) derivatives as chiral agents were used at four different pH values to study the enantioseparation of the differently protonated guest molecules. The separation was optimized as a function of CD concentration, buffer type and concentration, pH and applied voltage. For the tosylated derivate the best resolution (R(s)=2.76) was found with 6-monodeoxy-6-mono-(3-hydroxy)-propylamino-beta-cyclodextrin hydrochloride (PA-beta-CD) at pH 6.8, while with the same selector at pH 7.2 enantioseparation with an R(s) value of 4.32 could be achieved for the dansylated pregabalin. At pH 2.5 for the dansylated derivative trimethylated alpha- and beta-CD systems resulted the most significant separation (R(s)=7.38 and R(s)=7.74, respective...Continue Reading

References

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Citations

Oct 11, 2011·Chemistry Central Journal·Alka Bali, Prateek Gaur
Jul 22, 2014·Journal of Pharmaceutical and Biomedical Analysis·Krisztina NémethJúlia Visy
Dec 7, 2010·Journal of Pharmaceutical and Biomedical Analysis·Gerhard K E Scriba
Nov 12, 2013·Journal of Pharmaceutical and Biomedical Analysis·Ida FejősSzabolcs Béni
Nov 22, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lakshmi Narayana ChennuruPilar Franco
Nov 20, 2012·Electrophoresis·Despina A TsioupiConstantina P Kapnissi-Christodoulou
May 24, 2014·Electrophoresis·Pavel RezankaDavid Sýkora
Aug 7, 2018·Journal of Forensic Sciences·Michael L Hitchcock, Ioan Marginean
Jan 4, 2012·Electrophoresis·Véréna PoinsotFrançois Couderc
Mar 7, 2013·Electrophoresis·Juana RodríguezLorena Muñoz
Mar 1, 2011·Analytical Methods : Advancing Methods and Applications·Huang Lu, Guonan Chen
Jan 21, 2021·Rapid Communications in Mass Spectrometry : RCM·Liancheng GuChuan-Fan Ding
Aug 22, 2020·Journal of Chromatography. a·Ida FejősSzabolcs Béni
Jun 24, 2021·International Journal of Analytical Chemistry·Chanbasha Basheer
Dec 14, 2011·Analytical Chemistry·Matthew GeigerMichael T Bowser
Nov 9, 2021·Luminescence : the Journal of Biological and Chemical Luminescence·Mohamed A Abdel HamidHany A Batakoushy

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