(<i>S</i>)‐(−)‐<i>N</i>‐(Pentafluorobenzylcarbamoyl)prolyl chloride: a chiral derivatisation reagent designed for gas chromatography/negative ion chemical ionisation mass spectrometry of amino compounds

Leis, Hans Jörg; Windischhofer, Werner

doi:10.1002/rcm.6146

Cited by 5 publications

(4 citation statements)

References 35 publications

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“…A highly sensitive and robust analytical method is needed for the analysis of MPH in these differing environments. Over the last decade, a broad range of methods has been applied for MPH analysis, among them liquid chromatography (LC), capillary electrophoresis (CE), gas chromatography (GC) and enzyme‐linked immunosorbent assays (ELISA) . Immunoassays often lack in specificity and need GC‐MS or LC‐MS in addition to ensure a unique determination of the substance .…”

Section: Introductionmentioning

confidence: 99%

“…However, sensitivity is low compared with other techniques. MPH chiral separation can also be achieved using conventional methods such as GC‐MS . The majority of MPH studies is based on separation by LC followed by various detection methods such as fluorescence (FL), peroxyoxalate chemiluminescence (PO‐CL), and mass spectrometry (MS) or tandem mass spectrometry (MS/MS).…”

Section: Introductionmentioning

confidence: 99%

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Fast quantitative determination of methylphenidate levels in rat plasma and brain ex vivo by MALDI‐MS/MS

et al. 2015

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This study presents a simple and sensitive high-throughput matrix-assisted laser desorption/ionization time-of-flight tandem mass spectrometry (MALDI-MS/MS) method for ex vivo quantification of methylphenidate (MPH) in rat plasma and brain. The common MALDI matrix alpha-cyano-4-hydroxycinnamic acid was used to obtain an optimal dried droplet preparation. For method validation, standards diluted in plasma and brain homogenate prepared from untreated (control) rats were used. MPH was quantified within a concentration range of 0.1-40 ng/ml in plasma and 0.4-40 ng/ml in brain homogenate with an excellent linearity (R ≥ 0.9997) and good precision. The intra-day and inter-day accuracies fulfilled the FDA's ±15/20 critera. The recovery of MPH ranged from 93.8 to 98.5% and 87.2 to 99.8% in plasma and homogenate, respectively. We show that MPH is successfully quantified in plasma and brain homogenate of rats pre-treated with this drug using the internal standard calibration method. By means of this method, a linear correlation between plasma and brain concentration of MPH in rodents pre-treated with MPH was detected. The simple sample preparation based on liquid-liquid extraction and MALDI-MS/MS measurement requires approximately 10 s per sample, and this significantly reduces analysis time compared with other analytical methods. To the best of our knowledge, this is the first MALDI-MS/MS method for quantification of MPH in rat plasma and brain. Copyright © 2015 John Wiley & Sons, Ltd.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Fast quantitative determination of methylphenidate levels in rat plasma and brain ex vivo by MALDI‐MS/MS

et al. 2015

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“…Hitherto, a number of strategies have been described and applied for the separation of the enantiomeric composition of chiral compounds . Among the diverse technologies, chromatographic‐based chiral resolution is the most widely used techniques, e.g., high‐performance liquid chromatography (HPLC),, capillary electrophoresis (CE), capillary electrochromatography (CEC), gas chromatography (GC), supercritical fluid chromatography (SFC), and simulated moving bed chromatography (SMB) have been successfully utilized for enantioseparation. One of the common features of these techniques is the use of one or a multiple of chiral selector(s) as stationary phase, chiral mobile additives, or chiral counterions.…”

Section: Introductionmentioning

confidence: 99%

Preparative Separation of Enantiomers Based on Functional Nucleic Acids Modified Gold Nanoparticles

et al. 2013

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The preparative-scale separation of chiral compounds is vitally important for the pharmaceutical industry and related fields. Herein we report a simple approach for rapid preparative separation of enantiomers using functional nucleic acids modified gold nanoparticles (AuNPs). The separation of DL-tryptophan (DL-Trp) is demonstrated as an example to show the feasibility of the approach. AuNPs modified with enantioselective aptamers were added into a racemic mixture of DL -Trp. The aptamer-specific enantiomer (L-Trp) binds to the AuNPs surface through aptamer-L-Trp interaction. The separation of DL-Trp is then simply accomplished by centrifugation: the precipitate containing L-Trp bounded AuNPs is separated from the solution, while the D-Trp remains in the supernatant. The precipitate is then redispersed in water. The aptamer is denatured under 95 °C and a second centrifugation is then performed, resulting in the separation of AuNPs and L-Trp. The supernatant is finally collected to obtain pure L-Trp in water. The results show that the racemic mixture of DL-Trp is completely separated into D-Trp and L-Trp, respectively, after 5 rounds of repeated addition of fresh aptamer-modified AuNPs to the DL-Trp mixture solution. Additionally, the aptamer-modified AuNPs can be repeatedly used for at least eight times without significant loss of its binding ability because the aptamer can be easily denatured and renatured in relatively mild conditions. The proposed approach could be scaled up and extended to the separation of other enantiomers by the adoption of other enantioselective aptamers.

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“…The most common approaches for chiral analysis are those based on chromatographic techniques, where the chiral selectors are deployed in the form of a stationary phase, chiral mobile additives, or a chiral counter ion. High performance liquid chromatography (HPLC), 6,7 gas chromatography (GC), 8,9 capillary electrophoresis (CE), [10][11][12] capillary electrochromatography (CEC), 13 and micellar electrokinetic chromatography (MEKC) 14,15 have been used for the separation and determination of chiral compounds. Meanwhile, our group is also involved in the development of chromatography based approaches for sensitive determination of enantiomers.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective analysis of melagatran via an LSPR biosensor integrated with a microfluidic chip

et al. 2012

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The impact of chiral compounds on pharmacological and biological processes is well known. With the increasing need for enantiomerically pure compounds, effective strategies for enantioseparation and chiral discrimination are in great demand. Herein we report a simple but efficient approach for the enantioselective determination of chiral compounds based on a localized surface plasmon resonance (LSPR) biosensor integrated with a microfluidic chip. A glass microfluidic chip with an effective volume of ~0.75 μL was fabricated for this application. Gold nanorods (AuNRs) with an aspect ratio of ~2.6 were self-assembled onto the surface of the inner wall of the chip to serve as LSPR transducers, which would translate the analyte binding events into quantitative concentration information. Human α-thrombin was immobilized onto the AuNR surface for enantioselective sensing of the enantiomers of melagatran. The proposed sensor was found to be highly selective for RS-melagatran, while the binding of its enantiomer, SR-melagatran, to the sensor was inactive. Under optimal conditions, the limit of detection of this sensor for RS-melagatran was found to be 0.9 nM, whereas the presence of 10,000-fold amounts of SR-melagatran did not interfere with the detection. To the best of our knowledge, this is the first demonstration of an LSPR-based enantioselective biosensor.

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(S)‐(−)‐N‐(Pentafluorobenzylcarbamoyl)prolyl chloride: a chiral derivatisation reagent designed for gas chromatography/negative ion chemical ionisation mass spectrometry of amino compounds

Cited by 5 publications

References 35 publications

Fast quantitative determination of methylphenidate levels in rat plasma and brain ex vivo by MALDI‐MS/MS

Fast quantitative determination of methylphenidate levels in rat plasma and brain ex vivo by MALDI‐MS/MS

Preparative Separation of Enantiomers Based on Functional Nucleic Acids Modified Gold Nanoparticles

Enantioselective analysis of melagatran via an LSPR biosensor integrated with a microfluidic chip

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