Recent advances on the use of cyclodextrins in the chiral analysis of drugs by capillary electrophoresis

Saz, J.M.; Marina, Marı́a Luisa

doi:10.1016/j.chroma.2016.08.029

Cited by 142 publications

(70 citation statements)

References 86 publications

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“…The separation time was prolonged following the increasing concentration of HS‐γ‐CD, because the viscosity of the buffer increased with the increasing of HS‐γ‐CD and the EOF decreased. Longer migration time could generate opportunities for interactions between the ATS and the cyclodextrin . When the chiral compound was combined with cyclodextrin, the chiral compound was absorbed into the hydrophobic hole of the cyclodextrin.…”

Section: Resultsmentioning

confidence: 99%

“…Longer migration time could generate opportunities for interactions between the ATS and the cyclodextrin. 32,33 When the chiral compound was combined with cyclodextrin, the chiral compound was absorbed into the hydrophobic hole of the cyclodextrin. The enantiomers were separated mainly by the weak interaction of the substituents on the chiral center with the hydroxyl groups on the cyclodextrin.…”

Section: Optimization Of Buffermentioning

confidence: 99%

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Simultaneous chiral analysis of amphetamine‐type stimulants and ephedrine by capillary electrophoresis coupled to time‐of‐flight mass spectrometry

et al. 2018

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This study focused on the chiral characteristics of methamphetamine seizures in Shanghai for inferring the synthetic pathways of drugs. Capillary electrophoresis coupled to time-of-flight mass spectrometry was used for simultaneous chiral separation of amphetamine-type stimulants and ephedrine, including S(+)-amphetamine/R(-)-amphetamine, S(+)-methamphetamine/R(-)-methamphetamine, (±)-MDA (3,4-methylenedioxyamphetamine), (±)-MDMA (3,4-methylenedioxymethamphetamine), (±)-MDEA (3,4-methylenedioxy-N-ethylamphetamine), d,l-N-ethylamphetamine, methylephedrine/methylpseudoephedrine, and 1S,2R(+)-ephedrine/(-)-ephedrine. The running buffer was 50-mM ammonium formate (pH 2.2 was adjusted by 1-M formic acid) containing 0.26% highly sulfated γ-cyclodextrin as the chiral selector. All enantiomers were well resolved within 40 minutes by capillary electrophoresis at 20 kV in an uncoated fused-silica capillary (50-μm I.D. × 375-μm O.D. × 90-cm length) and detected by micro time-of-flight mass spectrometry. Twenty seized methamphetamine samples were determined by the established method. They were classified into two groups through their chiral characteristics.

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Section: Resultsmentioning

confidence: 99%

Section: Optimization Of Buffermentioning

confidence: 99%

Simultaneous chiral analysis of amphetamine‐type stimulants and ephedrine by capillary electrophoresis coupled to time‐of‐flight mass spectrometry

et al. 2018

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“…A 1 H NMR study was performed to investigate the presence effect of the anionic ASP in a mixture of an analyte and CD on the proton chemical shifts of analytes. The mechanism of interaction of different analytes with several CDs was investigated in many papers . CDs, having a hydrophobic central cavity and hydrophilic outer surface, can act as an appropriate host for the hydrophobic guests.…”

Section: Resultsmentioning

confidence: 99%

“…Over the years, various CSs have been utilized in CE including cyclodextrins (CDs) and their derivatives, chiral crown ethers, chiral surfactants, ligand‐exchange complexes, linear polysaccharides like maltodextrins (MDs), and DNA oligonucleotides, to improve the enantioseparation capability of various classes of analytes . However, to improve the resolution of enantiomers, in some cases, dual systems by a combined use of two chiral reagents/modifiers in the BGE are applied for the chiral separation . Several combinations of the CSs and modifiers were reported until now, including the combinations of a CD and its neutral or ionic derivatives , CD and ionic liquids , CD and glycogen , CD and metal‐amino acid complex and a CD and a chiral surfactant .…”

Section: Introductionmentioning

confidence: 99%

Evaluation of the synergistic effect with amino acids for enantioseparation of basic drugs using capillary electrophoresis

et al. 2018

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The synergistic effect of two acidic amino acids, aspartic and glutamic acid, on the electrophoretic enantioseparation of four basic drugs was evaluated in the BGE containing a CD and at different pHs. Chlorpheniramine, hydroxyzine, propranolol and tramadol were used as the basic model drugs. However, no enantioseparations were achieved with a BGE containing sole amino acid, but the combined use of an acidic amino acid and a CD showed improved enantioseparations (synergistic effect) compared with the single CD system. The results demonstrated that at optimized pH, the electrostatic interactions of the anionic amino acids with the positively charged basic drugs could result in a decrease of the analyte migration velocity and it consequently improved the enantioseparation. The effective parameters such as the amino acid and chiral selector type and concentration, buffer pH, applied voltage, and capillary temperature were optimized. Favorable enantiomeric resolution and migration times of the model drugs were achieved with a 100 mM phosphate buffer solution (pH 3.0) containing 5.0 mM HP-α-CD/HP-β-CD and 20 mM aspartic acid with an 18 kV applied voltage at 25°C. H NMR experiments were also carried out in a mixture of an analyte and CD in the absence and presence of aspartic acid. The NMR results were consistent with the results obtained by CE which showed the synergistic effect of amino acid.

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“…Compared with classical techniques, CE has attracted increasing interest in chiral separation for its high resolution efficiency, low consumption of sample, solvent, and chiral selector, as well as high flexibility in choosing and changing types of selectors . As a significant class of chiral selector, β‐cyclodextrin (CD) and its derivatives are most widely used in CE . To improve the aqueous solubility and resolution ability of native CD, CD derivatives, including neutral and charged CDs (cationic and anionic CDs), have been introduced through chemical modification .…”

Section: Introductionmentioning

confidence: 99%

Chiral separation of 12 pairs of enantiomers by capillary electrophoresis using heptakis-(2,3-diacetyl-6-sulfato)-β-cyclodextrin as the chiral selector and the elucidation of the chiral recognition mechanism by computational methods

et al. 2017

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Chiral separation of 12 pairs of basic analyte enantiomers including oxybutynin, bambuterol, tradinterol, clenbuterol, clorprenaline, terbutaline, tulobuterol, citalopram, phencynonate, fexofenadine, salbutamol, and penehyclidine was conducted by capillary electrophoresis using a single-isomer anionic β-cyclodextrin derivative, heptakis-(2,3-diacetyl-6-sulfato)-β-cyclodextrin as the chiral selector. Parameters influencing separation were studied, including background electrolyte pH, heptakis-(2,3-diacetyl-6-sulfato)-β-cyclodextrin concentration, buffer concentration, and separation voltage. A background electrolyte consisting of 50 mM Tris-H PO and 6 mM heptakis-(2,3-diacetyl-6-sulfato)-β-cyclodextrin at pH 2.5 was found to be highly efficient for the separation of most enantiomers, with other conditions of normal polarity mode at 10 kV, detection wavelength of 210 nm using hydrodynamic injection for 3 s. Under the optimal conditions, baseline resolution (>1.50) for 11 pairs of enantiomers and somewhat lower resolution for penehyclidine enantiomers (1.17) were generated. Moreover, the possible mechanism of separation of clenbuterol, oxybutynin, salbutamol, and penehyclidine was investigated using a computational modeling method.

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Recent advances on the use of cyclodextrins in the chiral analysis of drugs by capillary electrophoresis

Cited by 142 publications

References 86 publications

Simultaneous chiral analysis of amphetamine‐type stimulants and ephedrine by capillary electrophoresis coupled to time‐of‐flight mass spectrometry

Simultaneous chiral analysis of amphetamine‐type stimulants and ephedrine by capillary electrophoresis coupled to time‐of‐flight mass spectrometry

Evaluation of the synergistic effect with amino acids for enantioseparation of basic drugs using capillary electrophoresis

Chiral separation of 12 pairs of enantiomers by capillary electrophoresis using heptakis-(2,3-diacetyl-6-sulfato)-β-cyclodextrin as the chiral selector and the elucidation of the chiral recognition mechanism by computational methods

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