Liquid chromatographic retention behavior and enantiomeric separation of three chiral center β‐blocker drug (nadolol) using heptakis (6‐azido‐6‐deoxy‐2, 3‐di‐O‐phenylcarbamolyted) β‐cyclodextrin bonded chiral stationary phase

Wang, Xin; Ching, Chi Bun

doi:10.1002/chir.10141

Cited by 20 publications

(23 citation statements)

References 27 publications

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“…Hence, taking into account the unique properties of cyclodextrins to generate hydrophobic cavities with hydrophilic exterior faces in aqueous solutions, the chiral discrimination between R-LC and S-LC will be due to the differences in their steric fit in the chiral cavities and their ability to establish hydrogen bonds. However, other intermolecular interactions may contribute for the enantiomeric resolution [18,20].…”

Section: Resultsmentioning

confidence: 99%

Simultaneous and enantioselective liquid chromatographic determination of eslicarbazepine acetate, S-licarbazepine, R-licarbazepine and oxcarbazepine in mouse tissue samples using ultraviolet detection

Alves

Figueiredo

Castel‐Branco

et al. 2007

Analytica Chimica Acta

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Herein is reported, for the first time, a simple and reliable chiral reversed-phase liquid chromatographic method coupled to ultraviolet (UV) detection for simultaneous determination of eslicarbazepine acetate (ESL) and its metabolites, S-licarbazepine (S-LC), R-licarbazepine (R-LC) and oxcarbazepine (OXC), in mouse plasma and brain, liver and kidney tissue homogenates. All analytes and the internal standard were extracted from plasma and tissue homogenates by a solid-phase extraction procedure using Waters Oasis ® hydrophilic-lipophilic balance cartridges. The chromatographic separation was performed by isocratic elution with water/methanol (88:12, v/v), pumped at a flow rate of 0.7 mL min −1 , on a Lichro-CART 250-4 ChiraDex (␤-cyclodextrin, 5 m) column at 30• C. The UV detector was set at 225 nm. Calibration curves were linear (r 2 ≥ 0.996) in the ranges 0.4-8 g mL −1 , 0.1-1.5 g mL −1 and 0.1-2 g mL −1 for ESL and OXC and in the ranges 0.4-80 g mL −1 , 0.1-15 g mL −1 and 0.1-20 g mL −1 for R-LC and S-LC in plasma, brain and liver/kidney homogenates, respectively. The overall precision not exceeded 11.6% (%CV) and the accuracy ranged from −3.79 to 3.84% (%bias), considering all analytes in all matrices. Hence, this method will be a useful tool to characterize the pharmacokinetic disposition of ESL in mice.

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Section: Resultsmentioning

confidence: 99%

Simultaneous and enantioselective liquid chromatographic determination of eslicarbazepine acetate, S-licarbazepine, R-licarbazepine and oxcarbazepine in mouse tissue samples using ultraviolet detection

Alves

Figueiredo

Castel‐Branco

et al. 2007

Analytica Chimica Acta

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“…Encouraged by the previous reports on the successful use of S-b-CD for the separation of nadolol and labetalol stereoisomers [28][29][30], we employed S-b-CD in combination with poly-L-SUCIL. In Fig.…”

Section: Effect Of Charged Cds and Synergismmentioning

confidence: 99%

“…The separations of nadolol and labetalol have been attempted via high-performance liquid chromatog-raphy (HPLC) using native CD or derivatized CD columns [29], or in supercritical fluid chromatography (SFC) using a 1 -acid glycoprotein column [30]. Although, the recent analytical applications of vancomycin column in HPLC for separation of these multichiral-center b-blockers seems promising [32].…”

Section: Introductionmentioning

confidence: 99%

“…Nadolol is extensively employed in the treatment of hypertension and angina pectoris. A racemate mixture of (RSR)-nadolol and (SRS)-nadolol is considered more potent than the racemate mixture of (SSR)-nadolol and (RRS)-nadolol [28][29][30]. Since nadolol has three stereogenic centers it should result in eight possible stereoisomers.…”

Section: Introductionmentioning

confidence: 99%

“…Compared to other separation techniques, CE is a more suitable technique for the analytical-scale separation of compounds with multiple stereogenic centers. For example, recent application of hepta-6-sulfate-b-CD as chiral selector in acidic and neutral BGE has demonstrated CE a viable technique for separation of four isomers of both labetalol [28,29] and nadolol [28]. In this study, we report the chiral recognition of two alkenoxy amino acid micelle polymers, poly-L-SUCL and poly-L-SUCIL in MEKC for separation of multichiral-center b-blockers, labetalol and nadolol.…”

Section: Introductionmentioning

confidence: 99%

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Polymeric alkenoxy amino acid surfactants: II. Chiral separations of β‐blockers with multiple stereogenic centers

2004

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Two amino acid-based (leucine and isoleucine) alkenoxy micelle polymers were employed in this study for the separation of multichiral center-bearing beta-blockers, nadolol and labetalol. These polymers include polysodium N-undecenoxy carbonyl-L-leucinate (poly-L-SUCL) and polysodium N-undecenoxy carbonyl-L-isoleucinate (poly-L-SUCIL). Detailed synthesis and characterization were reported in our previous paper [26]. It was found that poly-L-SUCIL gives better chiral separation than poly-L-SUCL for both nadolol and labetalol isomers. The use of 50-100 mM poly-L-SUCIL as a single chiral selector provided separation of four and three isomers of labetalol and nadolol, respectively. Further optimization in separation of both enantiomeric pairs of nadolol and labetalol was achieved by evaluation of type and concentration of organic solvents, capillary temperature as well type and concentration of cyclodextrins. A synergistic approach, using a combination of poly-L-SUCIL and sulfated beta-CD (S-beta-CD) was evaluated and it showed dramatic separation for enantiomeric pairs of nadolol. On the other hand for labetalol enantiomers, separation was slightly decreased or remain unaffected using the dual chiral selector system. Finally, simultaneous separation of both nadolol and labetalol enantiomers was achieved in a single run using 25 mM poly-L-SUCIL and 5% w/v of S-beta-CD in less then 35 min highlighting the importance of high-throughput chiral analysis.

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Probability rule for chiral recognition

Kafri

Lancet

2004

Chirality

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Molecular Chirality is of central interest in biological studies because enantiomeric compounds, while indistinguishable by most inanimate systems, show profoundly different properties in biochemical environments. Enantioselective separation methods, based on the differential recognition of two optical isomers by a chiral selector, have been amply documented. Also, great effort has been directed towards a theoretical understanding of the fundamental mechanisms underlying the chiral recognition process. Here we report a comprehensive data examination of enantio separation measurements for over 72000 chiral selector-select and pairs from the chiral selection compendium CHIRBASE. The distribution of alpha = k'(D)/k'(L) values was found to follow a power law, equivalent to an exponential decay for chiral differential free energies. This observation is experimentally relevant in terms of the number of different individual or combinatorial selectors that need to be screened in order to observe alpha values higher than a preset minimum. A string model for enantiorecognition (SMED) formalism is proposed to account for this observation on the basis of an extended Ogston three-point interaction model. Partially overlapping molecular interaction domains are analyzed in terms of a string complementarity model for ligand-receptor complementarity. The results suggest that chiral selection statistics may be interpreted in terms of more general concepts related to biomolecular recognition.

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Liquid chromatographic retention behavior and enantiomeric separation of three chiral center β‐blocker drug (nadolol) using heptakis (6‐azido‐6‐deoxy‐2, 3‐di‐O‐phenylcarbamolyted) β‐cyclodextrin bonded chiral stationary phase

Cited by 20 publications

References 27 publications

Simultaneous and enantioselective liquid chromatographic determination of eslicarbazepine acetate, S-licarbazepine, R-licarbazepine and oxcarbazepine in mouse tissue samples using ultraviolet detection

Simultaneous and enantioselective liquid chromatographic determination of eslicarbazepine acetate, S-licarbazepine, R-licarbazepine and oxcarbazepine in mouse tissue samples using ultraviolet detection

Polymeric alkenoxy amino acid surfactants: II. Chiral separations of β‐blockers with multiple stereogenic centers

Probability rule for chiral recognition

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