title: Liquid chromatographic resolution of mexiletine and its analogs on crown ether-based chiral stationary phases.
abstract: 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)).
authors.affiliation: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan, Republic of Korea.
authors.forename: Kab Bong
authors.initials: KB
authors.lastname: Jin
authors.forename: Hee Eun
authors.initials: HE
authors.lastname: Kim
authors.forename: Myung Ho
authors.initials: MH
authors.lastname: Hyun
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D043844:Crown Ethers / Q000737:chemistry*; D008801:Mexiletine / Q000031:analogs & derivatives / Q000737:chemistry* / Q000302:isolation & purification*; D013237:Stereoisomerism
chemical_list: D043844:Crown Ethers; D008801:Mexiletine
keywords: chiral stationary phase; enantiomer separation; liquid chromatography; mexiletine; mexiletine analogs