Chiral separations of some β‐adrenergic agonists and antagonists on AmyCoat column by HPLC

Ali, Imran; Saleem, Kishwar; Gaitonde, Vinay D.; Aboul‐Enein, Hassan Y.; Hussain, İqbal

doi:10.1002/chir.20697

Cited by 39 publications

(26 citation statements)

References 11 publications

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“…Therefore, it may be concluded that π‐π interactions are the major controlling forces in the chiral separation. This fact has already been published by our group . Briefly, the enantiomers of these drugs fitted stereospecifically in the chiral groove.…”

Section: Mechanism Of Separation At the Supramolecular Levelmentioning

confidence: 78%

Enantiomeric Separation and Simulation Studies of Pheniramine, Oxybutynin, Cetirizine, and Brinzolamide Chiral Drugs on Amylose‐Based Columns

et al. 2014

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Solid phase extraction (SPE)-chiral separation of the important drugs pheniramine, oxybutynin, cetirizine, and brinzolamide was achieved on the C18 cartridge and AmyCoat (150 x 46 mm) and Chiralpak AD (25 cm x 0.46 cm id) chiral columns in human plasma. Pheniramine, oxybutynin, cetirizine, and brinzolamide were resolved using n-hexane-2-PrOH-DEA (85:15:0.1, v/v), n-hexane-2-PrOH-DEA (80:20:0.1, v/v), n-hexane-2-PrOH-DEA (70:30:0.2, v/v), and n-hexane-2-propanol (90:10, v/v) as mobile phases. The separation was carried out at 25 ± 1 ºC temperature with detection at 225 nm for cetirizine and oxybutynin and 220 nm for pheniramine and brinzolamide. The flow rates of the mobile phases were 0.5 mL min(-1). The retention factors of pheniramine, oxybutynin, cetirizine and brinzolamide were 3.25 and 4.34, 4.76 and 5.64, 6.10 and 6.60, and 1.64 and 2.01, respectively. The separation factors of these drugs were 1.33, 1.18, 1.09 and 1.20 while their resolutions factors were 1.09, 1.45, 1.63 and 1.25, and 1.15, respectively. The absolute configurations of the eluted enantiomers of the reported drugs were determined by simulation studies. It was observed that the order of enantiomers elution of the reported drugs was S-pheniramine > R-pheniramine; R-oxybutynin > S-oxybutynin; S-cetirizine > R-cetirizine; and S-brinzolamide > R-brinzolamide. The mechanism of separation was also determined at the supramolecular level by considering interactions and modeling results. The reported SPE-chiral high-performance liquid chromatography (HPLC) methods are suitable for the enantiomeric analyses of these drugs in any biological sample. In addition, simulation studies may be used to determine the absolute configuration of the first and second eluted enantiomers.

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Section: Mechanism Of Separation At the Supramolecular Levelmentioning

confidence: 78%

Enantiomeric Separation and Simulation Studies of Pheniramine, Oxybutynin, Cetirizine, and Brinzolamide Chiral Drugs on Amylose‐Based Columns

et al. 2014

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“…It is attractive to report that the reported profens have a benzene ring facilitating π–π interactions among the antipodes and chiral amylose derivatives. It is already established that π–π interactions are crucial in the chiral separation of many aromatic racemates . The setting of all the antipodes of profens in the derivatized amylose grooves is depicted in Figures .…”

Section: Resultsmentioning

confidence: 99%

Chiral separation and modeling of baclofen, bupropion, and etodolac profens on amylose reversed phase chiral column

et al. 2017

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Chiral resolution of baclofen, bupropion, and etodolac profens was obtained with amylose derivatized chiral reversed stationary phase (carbamate groups). The eluent used for bupropion and etodolac was MeOH-water (20:80, v/v) and for baclofen was water-methanol (95:5, v/v). The eluent run rates, finding wavelength and temperature, were 1.0 mL/min, 220 nm and 27 ± 1 °C for all the eluents. The magnitude of the retardation factors for S- and R-enantiomers of baclofen, bupropion, and etodolac were 1.37, 2.62, 2.25, 3.25, 1.8, and 3.0. The magnitudes of separation and resolution factors were 1.90, 1.44, and 1.67 and 2.77, 2.35, and 2.04. Limits of detection and quantitation were 1.0-2.0 and 5.1-10.0 μg/mL. Chiral recognition mechanisms were recognized by simulation and high-performance liquid chromatography (HPLC) experiments. It was seen that hydrogen interactions, hydrophobic interactions, and π-π exchanges were the chief interactions for chiral recognition mechanisms. The described methods may be exploited for the chiral separation of baclofen, bupropion, and etodolac profens in any unknown sample.

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“…It is interesting to note that the reported dipeptide is aromatic, providing π–π interactions with chiral selectors. It is prominent that π–π forces are stronger than others participating in chiral separation . Therefore, these forces are accountable for the best chiral separation of the stereomers.…”

Section: Resultsmentioning

confidence: 99%

Chiral HPLC Separation and Modeling of Four Stereomers of DL‐Leucine‐DL‐Tryptophan Dipeptide on Amylose Chiral Column

et al. 2016

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Chiral high-performance liquid chromatography (HPLC) separation and modeling of four stereomers of DL-leucine-tryptophan DL-dipeptide on AmyCoat-RP column are described. The mobile phase applied was ammonium acetate (10 mM)-methanol-acetonitrile (50:5:45, v/v). The flow rate of the mobile phases was 0.8 mL/min with UV detection at 230 nm. The values of retention factors for LL-, DD-, DL-, and LD- stereomers were 2.25, 3.60, 5.00, and 6.50, respectively. The values of separation and resolution factors were 1.60, 1.39, and 1.30 and 7.76, 8.05, and 7.19. The limits of detection and quantitation were ranging from 1.0-2.3 and 5.6-14.0 μg/mL. The simulation studies established the elution orders and the mechanism of chiral recognition. It was seen that π-π connections and hydrogen bondings were the main forces for enantiomeric resolution. The reported chiral HPLC method may be applied for the enantiomeric separation of DL-leucine-DL-tryptophan in unknown matrices. Chirality 28:642-648, 2016. © 2016 Wiley Periodicals, Inc.

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Chiral separations of some β‐adrenergic agonists and antagonists on AmyCoat column by HPLC

Cited by 39 publications

References 11 publications

Enantiomeric Separation and Simulation Studies of Pheniramine, Oxybutynin, Cetirizine, and Brinzolamide Chiral Drugs on Amylose‐Based Columns

Enantiomeric Separation and Simulation Studies of Pheniramine, Oxybutynin, Cetirizine, and Brinzolamide Chiral Drugs on Amylose‐Based Columns

Chiral separation and modeling of baclofen, bupropion, and etodolac profens on amylose reversed phase chiral column

Chiral HPLC Separation and Modeling of Four Stereomers of DL‐Leucine‐DL‐Tryptophan Dipeptide on Amylose Chiral Column

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