Enantiomeric separation by HPLC of 1,4‐dihydropyridines with vancomycin as chiral selector

Boatto, Gianpiero; Nieddu, Maria; Faedda, Maria Virginia; Caprariis, P. De

doi:10.1002/chir.10238

Cited by 29 publications

(16 citation statements)

References 17 publications

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“…The enantioseparation of amlodipine in plasma, serum or urine was successfully carried out in LC using α1‐acid‐glycoprotein column 9, 10. Others LC methods using chiral stationary phases (CSPs) with vancomycin as the chiral selector were also reported for enantioseparation of amlodipine in bulk material with enantioresolution values lower than 2 11, 12. In capillary electrophoresis (CE), enantioresolution of amlodipine in biological fluids was performed using α‐ or β‐cyclodextrin as chiral selector 13–15.…”

Section: Introductionmentioning

confidence: 99%

Determination of enantiomeric purity of S‐amlodipine by chiral LC with emphasis on reversal of enantiomer elution order

Dossou

Edorh

Chiap³

et al. 2011

J of Separation Science

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An LC method was developed and prevalidated for the enantiomeric purity determination of S-amlodipine in polar organic solvent chromatography using a chlorine-containing cellulose-based chiral stationary phase (CSP). The concentration of formic acid (FA) (0.01-0.2%) in the mobile phase containing acetonitrile as the main solvent was found to influence the elution order of amlodipine enantiomers as well as the enantioresolution. A reversal of the enantiomer elution order of amlodipine was only observed with chiral stationary phases with both electron-withdrawing (chloro) and electron-donating groups (methyl) on the phenyl moieties of the chiral selector, namely cellulose tris(3-chloro-4-methylphenylcarbamate) and cellulose tris(4-chloro-3-methylphenylcarbamate). The highest enantioresolution (Rs : 4.1) value was obtained at the lowest FA concentration (0.01%) using cellulose tris(4-chloro-3-methylphenylcarbamate) as the chiral selector and the enantiomeric impurity, R-amlodipine, eluted first under these conditions. Therefore, the mobile phase selected for the prevalidation of the method consisted of ACN/0.1% DEA/0.01% FA and the temperature was set at 25°C. The method was prevalidated by means of the strategy based on the total measurement error and the accuracy profile. The method was found to be selective and the limit of quantification was found to be about 0.05% for R-amlodipine, while the limit of detection was close to 0.02%.

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Section: Introductionmentioning

confidence: 99%

Determination of enantiomeric purity of S‐amlodipine by chiral LC with emphasis on reversal of enantiomer elution order

Dossou

Edorh

Chiap³

et al. 2011

J of Separation Science

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“…Since IRD is a neutral DHP [8], it was decided to use a 50 mM sodium phosphate buffer pH 7.0 and 50 mM sodium borate buffer pH 9.3 as starting points. The effect of buffer type on the enantioseparation of IRD was assessed by performing electrophoretic separation.…”

Section: Choice Of Buffer and Chiral Selectormentioning

confidence: 99%

“…HPLC methods have also been reported for the enantioselective analysis of IRD employing stationary phase based on a 1 -acid glycoprotein [7,8], tetra-hydrophenanthrene p-systems [9], cellulose 4-tert-butylphenylcarbamate [10] and polysaccharide derivatives [11]. In addition, an LC/MS method was reported for the determination of degradation products from IRD [12].…”

Section: Introductionmentioning

confidence: 99%

Capillary electrophoresis method for the determination of isradipine enantiomers: Stability studies and pharmaceutical formulation analysis

2011

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A simple enantioselective method based on CE using CD as chiral selector was developed and validated for the determination of isradipine (IRD) enantiomers in a pharmaceutical formulation and for the determination of IRD enantiomers in degradation studies. After optimization, the best results were obtained using 15 mM borate buffer at pH 9.3 and sulfobutyl ether-β-cyclodextrin (2.5%, w/v) as chiral selector. The applied voltage was +30 kV, and the sample injection was performed in the hydrodynamic mode. All analyses were carried out in a fused-silica uncoated capillary with an id of 50 μm and total length of 60.0 cm. Under these conditions, a complete separation between IRD enantiomers was achieved in less than 7 min. Linearity was obtained in the range 50-300 μg/mL for both enantiomers (r≥0.9978). The RSD (%) and relative errors (%) obtained in precision and accuracy studies (intra-day and inter-day) were lower than 5%. Therefore, this method was found to be appropriate for controlling pharmaceutical formulations containing IRD enantiomers and the assay was considered to be stability indicating. The drug was subjected to oxidation, hydrolysis and photolysis. In all stress conditions the drug presented considerable degradation when compared with a fresh sample (zero time).

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“…vancomycin, teicoplanin and ristocetin A, etc.) have been successfully used as novel chiral selectors to resolve a variety of neutral and negatively charged enantiomers in LC, TLC and CE (Armstrong et al, 1994a(Armstrong et al, ,b, 1995Chen et al, 1995;Ward et al, 1995;Berthod et al, 1996;Rundlett et al, 1996;Ekborg-Ott et al, 1998a,b;Hrobonova et al, 2001;Chen, 2002;Boatto et al, 2003). These macrocyclic antibiotics make remarkable LC CSPs when covalently immobilized to a silica gel support and are similar in structure, with molecular weights ranging from 1500 to 2066.…”

Section: Introductionmentioning

confidence: 96%

The enantioseparation of amino acids on a teicoplanin chiral stationary phase using non-aqueous mobile phases after pre-column derivatization with sulfur-containing reagents: the considerations of mobile phase composition and analyte structure variation on resolution enhancement

Chen

2006

Biomed. Chromatogr.

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Amino acids were derivatized with sulfur-containing reagents in alkaline medium and enantioresolved by HPLC on a teicoplanin chiral stationary phase. Much better resolution was achieved using methanol-based mobile phase compared with elution with acetonitrile-based solvent mixture. The value of selectivity factor for many derivatives examined in the study can be easily several tenths of 100 or even exceed 100 in some cases. This magnitude of resolution is suitable for the preparative-scale application of isolating alpha-amino acid enantiomers in the derivatized form using a short column. The resolution is believed to be a result of the hydrogen bonding and steric hindrance by the nitrogen and sulfur atoms from the isothiocyanatyl fragment of the reagent, respectively, and is enhanced as the fragment is structurally phenylated (e.g. 2,4-difluorophenyl isothiocyanate and others examined in this study). The enhancement is even more significant if the aromatic moiety of the reagent becomes more acidic through halogenation with chlorine or fluorine for the stronger pi-pi interaction. However, this type of enhancement is offset to some extent and sometimes obscured by a chlorinated reagent that is relatively large in size as compared with the fluorinated one. Judging from the chromatographic data and the elution profile, the mechanisms leading to the resolutions are believed to be different under the elution of polar-organic mobile phases (i.e. methanol- and acetonitrile-based mobile phases).

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Enantiomeric separation by HPLC of 1,4‐dihydropyridines with vancomycin as chiral selector

Cited by 29 publications

References 17 publications

Determination of enantiomeric purity of S‐amlodipine by chiral LC with emphasis on reversal of enantiomer elution order

Determination of enantiomeric purity of S‐amlodipine by chiral LC with emphasis on reversal of enantiomer elution order

Capillary electrophoresis method for the determination of isradipine enantiomers: Stability studies and pharmaceutical formulation analysis

The enantioseparation of amino acids on a teicoplanin chiral stationary phase using non-aqueous mobile phases after pre-column derivatization with sulfur-containing reagents: the considerations of mobile phase composition and analyte structure variation on resolution enhancement

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