Enantiomeric separation of six beta‐adrenergic blockers on Chiralpak IB column and identification of chiral recognition mechanisms by molecular docking technique

Li, Meng; Jiang, Zhen; Di, Xin; Song, Yongbo

doi:10.1002/bmc.4803

Cited by 10 publications

(9 citation statements)

References 26 publications

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“…This tool facilitates prediction of most favored orientation of small molecules to interact with the stationary phase. The binding energies and the bond lengths of different interaction modes can be estimated with reasonable accuracy [ 22 , 23 ]. Further, it can help in understanding the elution behavior of the enantiomers based on binding energies.…”

Section: Resultsmentioning

confidence: 99%

“…Several analytical techniques have been used for enantiomeric separation of these drugs, namely, thin layer chromatography [ 10 ], surface enhanced Raman scattering [ 11 ], counter current chromatography [ 12 ], electrochromatography [ 13 , 14 ], capillary electrophoresis [ [15] , [16] , [17] , [18] ], high performance liquid chromatography (HPLC) [ 9 , [19] , [20] , [21] , [22] , [23] ], liquid chromatography-tandem mass spectrometry (LC-MS/MS) [ [24] , [25] , [26] , [27] , [28] , [29] ], and supercritical fluid chromatography (SFC) [ [30] , [31] , [32] , [33] ]. Among different chiral stationary phases (CSPs), polysaccharide (cellulose or amylose) based phases are the most widely used with these techniques [ 20 , 21 , 23 , 32 , 33 ]. Nikolai et al.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, Li et al. [ 23 ] reported enantiomeric separation of six β-blockers on Chiralpak IB column using HPLC and used molecular docking technique to understand the mechanism of chiral recognition. However, there are very few SFC based methods that report enantioseparation of the drugs studied in the present work.…”

Section: Introductionmentioning

confidence: 99%

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Simultaneous enantioseparation and simulation studies of atenolol, metoprolol and propranolol on Chiralpak® IG column using supercritical fluid chromatography

Pandya

Shah

Shrivastav

2021

Journal of Pharmaceutical Analysis

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Enantioseparation of three β-blockers, i.e., atenolol, metoprolol and propranolol, was studied on amylose tris(3-chloro-5-methylphenylcarbamate) immobilized chiral stationary phase using supercritical fluid chromatography (SFC). The effect of organic modifiers (methanol, isopropanol and their mixture), column temperature and back pressure on chiral separation of β-blockers was evaluated. Optimum chromatographic separation with respect to resolution, retention, and analysis time was achieved using a mixture of CO 2 and 0.1% isopropyl amine in isopropanol: methanol (50:50, V/V ), in 75:25 ( V/V ) ratio. Under the optimized conditions, the resolution factors ( R s ) and separation factors (α) were greater than 3.0 and 1.5, respectively. Further, with increase in temperature (25–45 °C) and pressure (100–150 bars) there was corresponding decrease in retention factors ( k ), α and R s . However, a reverse trend (α and R s ) was observed for atenolol with increase in temperature. The thermodynamic data from van't Hoff plots revealed that the enantioseparation was enthalpy driven for metoprolol and propranolol while entropy driven for atenolol. To understand the mechanism of chiral recognition and the elution behavior of the enantiomers, molecular docking studies were performed. The binding energies obtained from simulation studies were in good agreement with the elution order found experimentally and also with the free energy values. The method was validated in the concentration range of 0.5–10 μg/mL for all the enantiomers. The limit of detection and limit of quantitation ranged from 0.126 to 0.137 μg/mL and 0.376–0.414 μg/mL, respectively. The method was used successfully to analyze these drugs in pharmaceutical preparations.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Simultaneous enantioseparation and simulation studies of atenolol, metoprolol and propranolol on Chiralpak® IG column using supercritical fluid chromatography

Pandya

Shah

Shrivastav

2021

Journal of Pharmaceutical Analysis

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“…Although the ketoconazole enantiomers were not resolved in the normal-phase mode, the baseline ES of the analytes was achieved within 30 min under the reversed-phase mode. Another commercially available chiral cellulose-based column, Chiralpak ® IB (250 × 4.6 mm, i.d., 5 μm silica gel, Table 1), was employed by Li et al for the ES of six βadrenergic blockers (atenolol, bevantolol, carteolol, esmolol, metoprolol, and propranolol, Another commercially available chiral cellulose-based column, Chiralpak ® IB (250 × 4.6 mm, i.d., 5 µm silica gel, Table 1), was employed by Li et al for the ES of six β-adrenergic blockers (atenolol, bevantolol, carteolol, esmolol, metoprolol, and propranolol, Supplementary Materials Figure S8), using a mixture of n-hexane with either ethanol or isopropanol/0.1% diethylamine as a normal-phase eluant [32]. Ethanol allowed for better resolution of the six analytes than isopropanol.…”

Section: Applications Of Commercial Cellulose-based Chiral Columnsmentioning

confidence: 99%

“…Another commercially available chiral cellulose-based column, Chiralpak ® IB (250 × 4.6 mm, i.d., 5 μm silica gel, Table 1 ), was employed by Li et al for the ES of six β-adrenergic blockers (atenolol, bevantolol, carteolol, esmolol, metoprolol, and propranolol, Supplementary Materials Figure S8 ), using a mixture of n -hexane with either ethanol or isopropanol/0.1% diethylamine as a normal-phase eluant [ 32 ]. Ethanol allowed for better resolution of the six analytes than isopropanol.…”

Section: Cellulose-based Cspsmentioning

confidence: 99%

Polysaccharide- and β-Cyclodextrin-Based Chiral Selectors for Enantiomer Resolution: Recent Developments and Applications

Bui

Rosenau

2021

Molecules

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Polysaccharides, oligosaccharides, and their derivatives, particularly of amylose, cellulose, chitosan, and β-cyclodextrin, are well-known chiral selectors (CSs) of chiral stationary phases (CSPs) in chromatography, because they can separate a wide range of enantiomers. Typically, such CSPs are prepared by physically coating, or chemically immobilizing the polysaccharide and β-cyclodextrin derivatives onto inert silica gel carriers as chromatographic support. Over the past few years, new chiral selectors have been introduced, and progressive methods to prepare CSPs have been exploited. Also, chiral recognition mechanisms, which play a crucial role in the investigation of chiral separations, have been better elucidated. Further insights into the broad functional performance of commercially available chiral column materials and/or the respective newly developed chiral phase materials on enantiomeric separation (ES) have been gained. This review summarizes the recent developments in CSs, CSP preparation, chiral recognition mechanisms, and enantiomeric separation methods, based on polysaccharides and β-cyclodextrins as CSs, with a focus on the years 2019–2020 of this rapidly developing field.

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Advances and challenges in the pharmacokinetics and bioanalysis of chiral drugs

2022

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Enantioselective analytical approaches are essential for monitoring pharmacokinetics and acquiring accurate data to better understand the role of stereochemistry in pharmacokinetics. Enantioselectivity significantly impacts the pharmacokinetics of chiral drugs, especially in metabolic profile, leading to toxicity of enantiomer. Consequently, there is a need to study the pharmacokinetics of enantiomerically pure drugs and racemates as they differ in affinity with enzymes and proteins. Combining the best enantioseparation conditions with the specified biological matrix and the intended purpose of the analysis is a challenging task. This review discusses the importance of chirality in stereoselective pharmacokinetics with more relevant examples, various enantioselective analytical techniques, and stationary phases employed. Challenges such as lack of universal chiral columns, biological inversion of the isomers, and others have been discussed. Further presented the recent advances in the screening of chiral drugs and innovative improvements in the analytical approaches for chiral molecule analysis such as supercritical fluid chromatography, simulated moving bed chromatography, and other techniques are discussed.

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Enantiomeric separation of six beta‐adrenergic blockers on Chiralpak IB column and identification of chiral recognition mechanisms by molecular docking technique

Cited by 10 publications

References 26 publications

Simultaneous enantioseparation and simulation studies of atenolol, metoprolol and propranolol on Chiralpak® IG column using supercritical fluid chromatography

Simultaneous enantioseparation and simulation studies of atenolol, metoprolol and propranolol on Chiralpak® IG column using supercritical fluid chromatography

Polysaccharide- and β-Cyclodextrin-Based Chiral Selectors for Enantiomer Resolution: Recent Developments and Applications

Advances and challenges in the pharmacokinetics and bioanalysis of chiral drugs

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