Liquid chromatographic resolution of 1-aryl-1,2,3,4-tetrahydroisoquinolines on a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid

Lee, Areum; Jin, Kab Bong; Hyun, Myung Ho

doi:10.1016/j.chroma.2011.04.088

Cited by 19 publications

(19 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Our method used Chiralpak AS‐RH column consisting of silica gel coated with amylose tris[( S )‐ α ‐methylbenzylcarbamate] in reverse‐phase mode, although the previous direct methods employed amylose‐based CSP (Chiralpak AD) in normal‐phase mode or crown‐ether‐based CSP (Hanada et al ., ; Lee et al ., ). The present CSP was selected based on the preliminary experiments using amylose‐based CSPs (Chiralpak AD‐RH, AS‐RH and AY‐RH) and cellulose‐based CSPs (Chiralcel OD‐RH, OJ‐RH, and OZ‐RH).…”

Section: Discussionmentioning

confidence: 97%

Stereoselective analysis of flecainide enantiomers using reversed‐phase liquid chromatography for assessing CYP2D6 activity

Doki

Sekiguchi

Kuga

et al. 2014

Biomedical Chromatography

View full text Add to dashboard Cite

Stereoselective analyses of flecainide enantiomers were performed using reversed-phase high-performance liquid chromatography (HPLC) equipped with a polysaccharide-based chiral column (Chiralpak AS-RH) and fluorescence detector. Excitation and emission wavelengths were set at 300 and 370 nm, respectively. Flecainide enantiomers in serum and urine were extracted using diethyl ether. The mobile phase solution, comprising 0.1 m potassium hexafluorophosphate and acetonitrile (65:35, v/v), was pumped at a flow rate of 0.5 mL/min. The recoveries of flecainide enantiomers were greater than 94%, with the coefficients of variation (CVs) <6%. The calibration curves of flecainide enantiomers in serum and urine were linear in the concentration range 5-500 ng/mL and 0.75-15 µg/mL (r > 0.999), respectively. CVs in intra-day and inter-day assays were 1.8-5.8 and 3.4-7.5%, respectively. In a pharmacokinetic study, the ratios of (S)- to (R)-flecainide (S/R ratio) in the area under the curve and the amount of flecainide enantiomers excreted in urine were lower in a subject carrying CYP2D6*10/*10 than in subjects carrying CYP2D6*1/*2. The S/R ratio of trough serum flecainide concentration ranged from 0.79 to 1.16 in patients receiving oral flecainide. The present HPLC method can be used to assess hepatic flecainide metabolism in a pharmacokinetic study and therapeutic drug monitoring.

show abstract

Section: Discussionmentioning

confidence: 97%

Stereoselective analysis of flecainide enantiomers using reversed‐phase liquid chromatography for assessing CYP2D6 activity

Doki

Sekiguchi

Kuga

et al. 2014

Biomedical Chromatography

View full text Add to dashboard Cite

show abstract

“…) based on (+)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid was very successful in the resolution of α‐, β‐, and γ‐amino acids, fluoroquinolone compounds, amino alcohols and various primary amino compounds . CSP 1 was also very successful in the resolution of secondary amines . In addition, CSP 2 and CSP 3 (Fig.…”

Section: Introductionmentioning

confidence: 94%

Liquid Chromatographic Resolution of Mexiletine and Its Analogs on Crown Ether‐Based Chiral Stationary Phases

2014

Self Cite

View full text Add to dashboard Cite

Mexiletine, an effective class IB antiarrhythmic agent, and its analogs were resolved on three different crown ether-based chiral stationary phases (CSPs), one (CSP 1) of which is based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid and the other two (CSP 2 and CSP 3) are based on (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6. Mexiletine was resolved with a resolution (R(S)) of greater than 1.00 on CSP 1 and CSP 3 containing residual silanol group-protecting n-octyl groups on the silica surface, but with a resolution (R(S)) of less than 1.00 on CSP 2. The chromatographic behaviors for the resolution of mexiletine analogs containing a substituted phenyl group at the chiral center on the three CSPs were quite dependent on the phenoxy group of analytes. Namely, mexiletine analogs containing 2,6-dimethylphenoxy, 3,4-dimethylphenoxy, 3-methylphenoxy, 4-methylphenoxy, and a simple phenoxy group were resolved very well on the three CSPs even though the chiral recognition efficiencies vary with the CSPs. However, mexiletine analogs containing 2-methylphenoxy group were not resolved at all or only slightly resolved. Among the three CSPs, CSP 3 was found to show the highest chiral recognition efficiencies for the resolution of mexiletine and its analogs, especially in terms of resolution (R(S)).

show abstract

“…CSPs based on chiral crown ethers were very successful in the determination of enantiomeric composition of chiral compounds containing a primary amino group [12,[17][18][19]. While CSPs based on chiral crown ethers have been known to be effective for the resolution of racemic compounds containing a primary amino group through the enantioselective complexation of the primary ammonium group (R-NH3 + ) of analytes inside the cavity of the crown ether ring of the stationary phase [12,[17][18][19], interestingly CSP 1 (Figure 1) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid was found to be also quite successful in the resolution of racemic compounds containing a secondary amino group such as β-blockers [20], flecainide analogues [21], isoquinolines [22] and rasagiline analogues [23]. Fendiline also contains a secondary amino group and, in this instance, it is expected to be resolved on CSP 1.…”

Section: Introductionmentioning

confidence: 99%

Liquid Chromatographic Resolution of Fendiline and Its Analogues on a Chiral Stationary Phase Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid

Lee

Hyun

2014

Molecules

View full text Add to dashboard Cite

Abstract:Fendiline, an effective anti-anginal drug for the treatment of coronary heart diseases, and its sixteen analogues were resolved on a CSP based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid. Fendiline was resolved quite well with the separation factor (α) of 1.25 and resolution (RS) of 1.55 when a mobile phase consisting of methanolacetonitrile-trifluoroacetic acid-triethylamine at a ratio of 80/20/0.1/0.5 (v/v/v/v) was used. The comparison of the chromatographic behaviors for the resolution of fendiline and its analogues indicated that the 3,3-diphenylpropyl group bonded to the secondary amino group of fendiline is important in the chiral recognition and the difference in the steric bulkiness between the phenyl group and the methyl group at the chiral center of fendiline is also important in the chiral recognition.

show abstract

Liquid chromatographic resolution of 1-aryl-1,2,3,4-tetrahydroisoquinolines on a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid

Cited by 19 publications

References 34 publications

Stereoselective analysis of flecainide enantiomers using reversed‐phase liquid chromatography for assessing CYP2D6 activity

Stereoselective analysis of flecainide enantiomers using reversed‐phase liquid chromatography for assessing CYP2D6 activity

Liquid Chromatographic Resolution of Mexiletine and Its Analogs on Crown Ether‐Based Chiral Stationary Phases

Liquid Chromatographic Resolution of Fendiline and Its Analogues on a Chiral Stationary Phase Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid

Contact Info

Product

Resources

About