Separation of Basic Drug Enantiomers by Capillary Electrophoresis with New Glycosaminoglycan

Abstract

A new fucose-containing glycosaminoglycan was investigated as the chiral additive for the separation of basic drug enantiomers by capillary electrophoresis. Tolperisone and eperisone enantiomers were not separated with α- or β-cyclodextrin, or heparin as the chiral additive, but were separated with the new fucose-containing glycosaminoglycan. A variety of basic drug enantiomers were resolved using 2-5%(w/w) solution of the glycosaminoglycan in 10 mM phosphate buffer (final pH 5.0).

Capillary Electrophoresis

“…Nishi described the use of the dextrans and dextrins for separation of ionic compounds and further demonstrated the capabilities of chondroitin sulfates (linear sulfated polysaccharides) for enantioseparation of both neutral and ionic species (451). In addition, λ-carrageenan (452), a linear high-molecular-weight sulfated polysaccharide, was utilized for enantioresolution of weakly basic pharmaceuticals, while a fucose-containing glycosaminoglycan buffer additive afforded chiral resolution of some basic drugs that could not be resolved with CD or heparin additives (453).…”

Tolperisone: A Typical Representative of a Class of Centrally Acting Muscle Relaxants with Less Sedative Side Effects

“…Generally the racemic mixtures are used for medication. Interesting in this context are several analytical and preparative procedures that have been described, which allow the separation of the racemic mixtures into the pure stereo selective compounds (Armstrong et al 1991; Haginaka et al 1999; Matsunaga et al 2003; Tsukamoto et al 1997, 1999; Velmurugan et al 2002; Welch et al 1997). The current review will focus on the most important substance, on tolperisone, but will also deal with progress on related drugs, except silperisone (silperisone being covered by a recent review (Farkas 2006)).…”

Determination of the Molecular Mass of New l-Fucose-Containing Glycosaminoglycan and Its Distribution by High-Performance Gel-Permeation Chromatography with Laser Light-Scattering Detection

“…The influence of the molecular mass of the new glycosaminoglycan on separation of drug enantiomers is also discussed. 4,5 Thus, it is important to clarify the molecular masses of DHG and FGAG and their distributions. The method so far employed for determining the molecular mass of a biopolymer and its distribution includes a physicochemical technique, 6,7 high-performance gel permeation chromatography (HPGPC) [8][9][10][11][12][13] and gel electrophoresis.…”