Chromatographic and Computational Studies on the Chiral Recognition of Sulfated β-Cyclodextrin on Enantiomeric Separation of Milnacipran

Pathak, Pranav; Ec, Coutinho; Mohanraj, Krishnapriya; Martis, Elvis A. F.; Jain, Alok

doi:10.26434/chemrxiv.11726196.v2

Cited by 4 publications

(2 citation statements)

References 13 publications

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“…Sulfated β-cyclodextrin was used as a chiral mobile-phase additive for ES of the antidepressant drug milnacipran (Supplementary Materials Figure S38), under reversed-phase HPLC with a core-shell Kinetex C 8 column (150 × 4.6 mm, 5 µM), by Pathak et al [95]. A mobile phase consisting of 18:82 (v:v) acetonitrile/10 mM aqueous sodium dihydrogen phosphate buffer pH 3.0, containing 10 mM sulfated β-cyclodextrin, was ideal for resolving the milnacipran enantiomers.…”

Section: Preparation Developments and Methods Developmentmentioning

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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Section: Preparation Developments and Methods Developmentmentioning

confidence: 99%

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

Bui

Rosenau

2021

Molecules

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“…[12][13][14][15][16] Our laboratory has also worked on enantioseparation of few APIs using CMPA. 17,18,19 Previously, our research group has successfully separated enantiomers of milnacipran by CMPA technique, wherein sulfated β-cyclodextrin was added in the mobile phase as a chiral selector 19 .…”

Section: Figure 1: Structure Of Formoterolmentioning

confidence: 99%

Enantioselective Chromatographic Analysis of Formoterol Fumarate using Chiral Mobile Phase Additives and Achiral Core-Shell Column

Pathak

Mohanraj²

2020

Preprint

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<p>A simple, robust, cost-effective, and rapid RP-HPLC method was developed for the separation of enantiomers of formoterol. The separation was achieved by the chiral mobile phase additive technique on an achiral column. Formoterol is a bronchodilator that consists of 50:50 S, S-formoterol and R, R-formoterol. The bronchodilator activity is attributed to R, R-formoterol. Hence, it is important to develop a method to separate the enantiomers of formoterol. Various factors affecting enantiomeric resolution were investigated and optimized. The enantiomers of formoterol were successfully separated with a resolution of 2.57 with a run-time of 9 minutes. The method was validated in accordance with ICH guidelines. The validated method was successfully applied to the marketed formulation of arformoterol. </p>

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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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Chromatographic and Computational Studies on the Chiral Recognition of Sulfated β-Cyclodextrin on Enantiomeric Separation of Milnacipran

Cited by 4 publications

References 13 publications

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

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

Enantioselective Chromatographic Analysis of Formoterol Fumarate using Chiral Mobile Phase Additives and Achiral Core-Shell Column

Advances and challenges in the pharmacokinetics and bioanalysis of chiral drugs

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