Direct TLC resolution of atenolol and propranolol into their enantiomers using three different chiral selectors as impregnating reagents

Bhushan, Ravi; Tanwar, Shivani

doi:10.1002/bmc.1025

Cited by 46 publications

(29 citation statements)

References 23 publications

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“…Analytical methods so far used for chiral separations of these β-adrenergic antagonists include thin layer chromatography [4,5], HPLC [6–8], capillary electrochromatography [9,10], and capillary electrophoresis (CE) [11–14]. CE especially has attracted the greater interest for chiral separations.…”

Section: Introductionmentioning

confidence: 99%

Molecular Modeling Study of Chiral Separation and Recognition Mechanism of β-Adrenergic Antagonists by Capillary Electrophoresis

Liu

Tan

et al. 2012

IJMS

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Chiral separations of five β-adrenergic antagonists (propranolol, esmolol, atenolol, metoprolol, and bisoprolol) were studied by capillary electrophoresis using six cyclodextrins (CDs) as the chiral selectors. Carboxymethylated-β-cyclodextrin (CM-β-CD) exhibited a higher enantioselectivity power compared to the other tested CDs. The influences of the concentration of CM-β-CD, buffer pH, buffer concentration, temperature, and applied voltage were investigated. The good chiral separation of five β-adrenergic antagonists was achieved using 50 mM Tris buffer at pH 4.0 containing 8 mM CM-β-CD with an applied voltage of 24 kV at 20 °C. In order to understand possible chiral recognition mechanisms of these racemates with CM-β-CD, host-guest binding procedures of CM-β-CD and these racemates were studied using the molecular docking software Autodock. The binding free energy was calculated using the Autodock semi-empirical binding free energy function. The results showed that the phenyl or naphthyl ring inserted in the hydrophobic cavity of CM-β-CD and the side chain was found to point out of the cyclodextrin rim. Hydrogen bonding between CM-β-CD and these racemates played an important role in the process of enantionseparation and a model of the hydrogen bonding interaction positions was constructed. The difference in hydrogen bonding formed with the –OH next to the chiral center of the analytes may help to increase chiral discrimination and gave rise to a bigger separation factor. In addition, the longer side chain in the hydrophobic phenyl ring of the enantiomer was not beneficial for enantioseparation and the chiral selectivity factor was found to correspond to the difference in binding free energy.

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Section: Introductionmentioning

confidence: 99%

Molecular Modeling Study of Chiral Separation and Recognition Mechanism of β-Adrenergic Antagonists by Capillary Electrophoresis

Liu

Tan

et al. 2012

IJMS

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“…These include ligand exchange resolution via ChiralPlate ® (Martens et al, 1986) in the form of DL-5,5-dimethyl-4-thiazolidinecarboxylic acid, obtained by its cyclization with HCHO (and the cyclic derivative was also used to determine the enantiomeric purity of pharmaceutical D-PenA by ligand exchange HPLC; Busker et al, 1985), and in the form of its diastereomers prepared with Marfey's reagent and two of its structural variants (Bhushan et al, 2007) using both normal-phase and reversed-phase TLC (and also RP-HPLC). L-Tartaric acid has previously been used in this laboratory as a chiral impregnating reagent for direct TLC enantiomeric resolution of phenylthiohydantoin (PTH) derivatives of amino acids (Bhushan and Ali, 1987), racemic ephedrine and atropine (Bhushan et al, 2001), and racemic atenolol and propranolol (Bhushan and Tanwar, 2008).…”

Section: Introductionmentioning

confidence: 99%

Direct enantiomeric TLC resolution of dl‐penicillamine using (R)‐mandelic acid and l‐tartaric acid as chiral impregnating reagents and as chiral mobile phase additive

Bhushan

Agarwal

2008

Biomedical Chromatography

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DL-Penicillamine has been resolved into its enantiomers by normal-phase TLC using L-tartaric acid as chiral impregnating reagent as well as chiral mobile phase additive, while (R)-mandelic acid has been found to be successful as a chiral impregnating reagent. The solvent system acetonitrile-methanol-water (5:1:1, v/v) was found to be successful when L-tartaric acid was used as impregnating agent while the solvent combination acetonitrile-methanol-(0.5% l-tartaric acid in water, pH 5)-glacial acetic acid (7:1:1.1:0.7, v/v) was successful as mobile phase as it contained L-tartaric acid as the chiral additive. (R)-mandelic acid was successful as chiral impregnating reagent with ethyl acetate-methanol-water (3:1:1, v/v), as the mobile phase. The effects of concentration of chiral selectors, temperature and pH were examined on enantiomeric resolution. The spots were detected with iodine vapors and the detection limits were found to be 0.12 microg for each enantiomer of penicillamine with L-tartaric acid, under both the conditions, and 0.11 microg with (R)-mandelic acid.

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“…Their racemic compounds can be resolved to enantiomers by means of several analytical methods such as HPLC (Matchett et al, 1996, Park et al, 2000, Makamba et al 1998Haginaka et al, 1999, Henriksson et al, 1999, Sharma et al, 1995, GC (Gyllenhaal et al, 1985, Donnecke et al, 1996, Abe et al, 1995, Juvancz et al, 1993, TLC (Bhushan & Arora, 2003;Bhushan & Tanwar, 2008 or CE (Zhang et al, 2008, Beck & Neau, 2000Proksa, 1999;Proksa & Čižmáriková, 2001). The most widely technique used for separation of the enantiomers have been HPLC on different chiral stationary phases (CSP) such as β-cyclodextrin (Matchett et al, 1996;Park et al, 2000), immobilized proteins (Makamba et al, 1998, Haginaka et al, 1999, Henriksson et al, 1999, Pirkle-type phases (Petersen et al, 1997), and cellulose and amylose-based phases (Aboul-Enein & Bakr, 1998;Valentova et al, 2003).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and HPLC Enantioseparation of Derivatives of the 3-hydroxyphenylethanone

Cizmáriková

Némethy

Valentová

et al. 2012

Acta Facultatis Pharmaceuticae Universitatis Comenianae

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Within the framework of the study of the synthesis and high-performance liquid chromatography (HPLC) enantioseparation the series of 9 derivatives of 3-hydroxyphenylethanone was prepared by a well-tried method. The structure of the prepared compounds was confirmed on the basis of interpretation of the IR, UV, 1 H NMR and 13 C NMR spectra. An enantioseparation of prepared compounds was performed using HPLC on a native teicoplanin (Chirobiotic T) and the amylose tris (3,5-dimethylphenylcarbamate) (Chiralpak AD) chiral stationary phases, which is more suitable for the enantioseparation of all prepared compounds especially with heterocycles in the basic part of a molecule.

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Direct TLC resolution of atenolol and propranolol into their enantiomers using three different chiral selectors as impregnating reagents

Cited by 46 publications

References 23 publications

Molecular Modeling Study of Chiral Separation and Recognition Mechanism of β-Adrenergic Antagonists by Capillary Electrophoresis

Molecular Modeling Study of Chiral Separation and Recognition Mechanism of β-Adrenergic Antagonists by Capillary Electrophoresis

Direct enantiomeric TLC resolution of dl‐penicillamine using (R)‐mandelic acid and l‐tartaric acid as chiral impregnating reagents and as chiral mobile phase additive

Synthesis and HPLC Enantioseparation of Derivatives of the 3-hydroxyphenylethanone

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