Enantiomeric resolution of some nonsteroidal antiinflammatory and anticoagulant drugs using ?-cyclodextrins by capillary electrophoresis

Abstract

β‐cyclodextrin (CD) and its derivatives HP‐β‐CD, DM‐β‐CD, and TM‐β‐CD have been employed as chiral selectors for the separation of three nonsteroidal antiinflammatory drugs (NSAIDs) and anticoagulant at relatively low concentration (8–15 mM) by capillary zone electrophoresis (CZE). In this study, baseline separation was achieved for ibuprofen, ketoprofen, naproxen, and warfarin. It was found that the addition of 0.1% hydroxypropyl methyl cellulose (HPMC) was effective for separation. Under these conditions, the S‐(+) enantiomer eluted before R‐(−) in terms of ibuprofen; the calculated energy values obtained from the molecular modeling correlated well with the elution order. An equation for calculating the pKa values by capillary electrophoresis was introduced, and the pKa values of the four chiral drugs at 25°C were obtained based on the equation. The value pKa + 0.5 is proposed to be the suitable pH of the background electrolyte for the separation of chiral compounds containing a carboxylic group. Chirality 11:56–62, 1999. © 1999 Wiley‐Liss, Inc.

Enantioselective analysis of ibuprofen in human plasma by anionic cyclodextrin-modified electrokinetic chromatography

“…In preliminary experiments, various natives (a-, b-and g-CD) and neutral CD derivatives (hydroxypropyl-b-CD, TMb-CD and amphoteric b-CD) were investigated under basic conditions (pH.7.0), but chiral recognition was not obtained for IBU under the used conditions. Otherwise, several authors have achieved the resolution of IBU using TMb-CD and internally polyacrylamide-coated capillaries [50,26,29] or fused-silica capillaries [23,25]. Mixtures of TMb-CD and a linear dextrin [31] or an anionic CD derivative (sulfobuthyl ether or carboxymethyl-b-CD) were also used [28].…”

“…Several chiral selectors have been demonstrated to be potential chiral discriminators in CE for direct and rapid separation of IBU enantiomers, such as neutral [20][21][22][23][24][25][26] and charged [27][28][29] b-cyclodextrin (CD) derivatives, linear oligosaccharides [30][31][32], macrocyclic antibiotics such as vancomicin and ristocetin A [33][34][35]. In addition, open-tubular capillary electrochromatography with an immobilized polysiloxane-anchored permethyl-b-CD [36] was also used.…”

Comparative Enantioseparation of Ketoprofen with Trimethylated α‐, β‐, and γ‐Cyclodextrins in Capillary Electrophoresis and Study of Related Selector–Selectand Interactions Using Nuclear Magnetic Resonance Spectroscopy

“…Several methods for the separation of the KT enantiomers by using CE have been reported. [20][21][22][23][24][25][26][27] One study describes the separation of the enantiomers by high-performance liquid chromatography using hydroxypropyl-b-CyD as the chiral additive to the mobile phase. 28 In few of the studies employing CE, the enantiomer migration or elution order in the presence of heptakis(2,3,6-tri-O-methyl)-b-CyD (TM-b-CyD) as chiral selector has been determined.…”

Optimization of gas chromatographic method for the enantioseparation of arylpropionic non-steroidal anti-inflammatory drug methyl esters

“…There are several papers on HPLC determination of either chiral derivatives of 2-arylpropionic acids or direct determination of 2-arylpropionic acids enantiomers [18][19][20][21]. There are also many CE methods for determination of 2-arylpropionic acids enantiomers involving different chiral buffer additives used for method optimization [22][23][24][25][26][27][28][29]. In previously mentioned papers [14,15] esterification is stereoselective and no GC chiral separation analysis on obtained esters was done.…”