Optimization of preparative electrophoretic chiral separation of ritalin enantiomers

Schneiderman, Eva; Gratz, Samuel R.; Stalcup, Apryll M.

doi:10.1016/s0731-7085(01)00572-6

Cited by 8 publications

(11 citation statements)

References 35 publications

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“…Migration velocities depend on mobility of the analyte, which can be optimized through changes in buffer ionic strength and pH (Boone et al , ). Reported enantiomer separations of d,l‐ threo ‐MPH by CE are performed in CZE mode and involve the addition of chiral selectors (Bach and Henion, ; Boone et al , ; Denk et al , ; Huang et al , ; Lee et al , ; Schneiderman et al , ; Theurillat and Thormann, ). CE chiral separations of d‐l‐ threo ‐MPH utilized cyclodextrins (CD) and their derivatives as chiral selectors (Ward and Hamburg, ).…”

Section: Capillary Electrophoresis Methodsmentioning

confidence: 99%

“…The three main types of CDs, α ‐, β ‐ and γ ‐, contain six, seven and eight glucose monomers, respectively, arranged into a ring structure. β ‐CD derivatives are employed for the enantioseparation of threo ‐MPH (Denk et al ., ; Huang et al , ; Lee et al ., ; Schneiderman et al ., ; Theurillat and Thormann, ), as it was observed that both α ‐ and γ ‐CDs were unable to interact with MPH enantiomers (Lee et al ., ). Furthermore, the addition of the chiral selector, heptakis (2,6‐di‐ O ‐methyl)‐ β ‐CD (DM‐ β ‐CD), to phosphate buffer solutions is necessary for successful separation of MPH and RA enantiomers in two different assays (Denk et al ., ; Huang et al ., ).…”

Section: Capillary Electrophoresis Methodsmentioning

confidence: 99%

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Chromatographic and electrophoretic strategies for the chiral separation and quantification of d‐ and l‐threo methylphenidate in biological matrices

Allen

Pond

2014

Biomedical Chromatography

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Commercially available methylphenidate (MPH) exists as a racemic mixture composed of the d- and l-threo enantiomers. Various pharmacokinetic studies of MPH have shown a greater pharmacological potency of the d-threo enantiomer. Furthermore, it was deduced that the stereoselective cleavage of MPH to produce ritalinic acid (RA) by human carboxylesterase results in a higher oral bioavailability of the d-threo enantiomer. As a requirement for pharmaceutical regulation authorities, efforts have been made to determine the differential biological distribution of d- and l-threo MPH and RA enantiomers. In support of these efforts, numerous analytical procedures have been developed for the chiral separation and quantification of MPH enantiomers in a variety of biological matrices. The available methodologies accomplish the enantioseparation and quantification of MPH using gas chromatography, liquid chromatography or capillary electrophoretic techniques coupled with a variety of detectors. The current review discusses the technical procedures involved, and the sensitivity and selectivity of these assays.

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Section: Capillary Electrophoresis Methodsmentioning

confidence: 99%

Section: Capillary Electrophoresis Methodsmentioning

confidence: 99%

Chromatographic and electrophoretic strategies for the chiral separation and quantification of d‐ and l‐threo methylphenidate in biological matrices

Allen

Pond

2014

Biomedical Chromatography

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“…Vigh and co-workers [69][70][71][72] developed methods utilizing free-flow isoelectric focusing [69][70][71] and isoelectric trapping techniques [72] in the presence of neutral and sulfated CD derivatives for the preparative isolation of drug enantiomers. Continuous free-flow electrophoresis has been used for the preparative enantioseparation of ritalin using randomly sulfated b-CD as chiral selector [73]. The continuous fractionation of the enantiomers of piperoxan in free solution by an electrophoretic analog of simulated moving bed chromatography has been reported [74].…”

Section: Separation Of Drug Enantiomersmentioning

confidence: 99%

Pharmaceutical and biomedical applications of chiral capillary electrophoresis and capillary electrochromatography: An update

Scriba¹

2003

Electrophoresis

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Pharmaceutical and biomedical applications of chiral capillary electrophoresis and capillary electrochromatography: An updateCapillary electrophoresis is often considered an ideal method for the chiral analysis of compounds due to the high separation power of the technique and has therefore found widespread acceptance for the analysis of drugs and pharmaceuticals. In contrast, capillary electrochromatography is still more or less in an infancy state searching for its place among the analytical separation techniques although interesting applications have been published. The present review summarizes recent developments and applications of chiral pharmaceutical analysis by electromigration techniques published in 2002 and early 2003.

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“…Enantiomeric CE separation is based upon differential interaction between analytes and one or multiple chiral selectors that are added to the running buffer and this technology was successfully applied to bioanalytical drug monitoring . Separations of methylphenidate stereoisomers by CE in presence of various modified CDs as chiral selectors were reported from different laboratories , whereas only one paper deals with their analysis in a body fluid .…”

Section: Introductionmentioning

confidence: 99%

Monitoring of threo‐methylphenidate enantiomers in oral fluid by capillary electrophoresis with head‐column field‐amplified sample injection

Theurillat

Thormann

2013

Electrophoresis

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Threo-methylphenidate is a chiral psychostimulant drug widely prescribed to treat attention-deficit hyperactivity disorder in children and adolescents. An enantioselective CE-based assay with head-column field-amplified sample stacking for analysis of threo-methylphenidate enantiomers in liquid/liquid extracts of oral fluid is described. Analytes are electrokinetically injected across a short water plug placed at the capillary inlet and become stacked at the interface between plug and buffer. Enantiomeric separation occurs within a few minutes in a pH 3.0 phosphate/triethanolamine buffer containing 20 mg/mL (2-hydroxypropyl)-β-CD as chiral selector. The assay with six point multilevel internal calibration provides a linear response for each enantiomer in the 10-200 ng/mL concentration range, is simple, inexpensive, and reproducible, and has an LOQ of 5 ng/mL. It was applied to oral fluid patient samples that were collected up to 12 h after intake of an immediate release tablet and two different extended release formulations with racemic methylphenidate. Drug profiles could thereby be assessed in a stereoselective way. Almost no levorotary threo-methylphenidate enantiomer was detected after intake of the two extended release formulations, whereas this enantiomer was detected during the first 2.5 h after intake of the immediate release preparation. The noninvasive collection of oral fluid is an attractive alternative to plasma for the monitoring of methylphenidate exposure in the pediatric community.

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Optimization of preparative electrophoretic chiral separation of ritalin enantiomers

Cited by 8 publications

References 35 publications

Chromatographic and electrophoretic strategies for the chiral separation and quantification of d‐ and l‐threo methylphenidate in biological matrices

Chromatographic and electrophoretic strategies for the chiral separation and quantification of d‐ and l‐threo methylphenidate in biological matrices

Pharmaceutical and biomedical applications of chiral capillary electrophoresis and capillary electrochromatography: An update

Monitoring of threo‐methylphenidate enantiomers in oral fluid by capillary electrophoresis with head‐column field‐amplified sample injection

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