title: Characterization of a single-isomer carboxymethyl-beta-cyclodextrin in chiral capillary electrophoresis.
abstract: In this work, the synthesis, characterization, and chiral capillary electrophoretic study of heptakis-(2,3-di-O-methyl-6-O-carboxymethyl)-β-CD (HDMCM), a single-isomer carboxymethylated CD, are presented. The pH-dependent and selector concentration-dependent enantiorecognition properties of HDMCM were investigated and discussed herein. The enantioseparation was assessed applying a structurally diverse set of noncharged, basic, and zwitterionic racemates. The increase in the selector concentration and gross negative charge of HDMCM improved the enantioseparation that could be observed in the majority of the cases. HDMCM was also successfully applied as BGE additive in NACE using a methanol-based system in order to prove the separation selectivity features and to highlight the broad applicability of HDMCM. Over 25 racemates showed partial or baseline separation with HDMCM under the conditions investigated, among which optimal enantiomer migration order was found for the four stereoisomers of tadalafil, tapentadol, and dapoxetine, offering the possibility of a chiral CE method development for chiral purity profiling of these drugs.
authors.affiliation: Department of Pharmacognosy, Semmelweis University, Budapest, Hungary.
authors.forename: Ida
authors.initials: I
authors.lastname: Fejős
authors.affiliation: Cyclolab Cyclodextrin Research & Development Laboratory, Ltd., Budapest, Hungary.
authors.forename: Erzsébet
authors.initials: E
authors.lastname: Varga
authors.affiliation: Cyclolab Cyclodextrin Research & Development Laboratory, Ltd., Budapest, Hungary.|Faculty of Science, Department of Organic Chemistry, Charles University in Prague, Prague, Czech Republic.
authors.forename: Gábor
authors.initials: G
authors.lastname: Benkovics
authors.affiliation: Cyclolab Cyclodextrin Research & Development Laboratory, Ltd., Budapest, Hungary.
authors.forename: Milo
authors.initials: M
authors.lastname: Malanga
authors.affiliation: Cyclolab Cyclodextrin Research & Development Laboratory, Ltd., Budapest, Hungary.
authors.forename: Tamás
authors.initials: T
authors.lastname: Sohajda
authors.affiliation: Cyclolab Cyclodextrin Research & Development Laboratory, Ltd., Budapest, Hungary.
authors.forename: Julianna
authors.initials: J
authors.lastname: Szemán
authors.affiliation: Department of Pharmacognosy, Semmelweis University, Budapest, Hungary.
authors.forename: Szabolcs
authors.identifier: 0000-0001-7056-6825
authors.initials: S
authors.lastname: Béni
mesh_terms: D019075:Electrophoresis, Capillary / Q000295:instrumentation / Q000379:methods*; D006863:Hydrogen-Ion Concentration; D000432:Methanol / Q000737:chemistry; D004364:Pharmaceutical Preparations / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D004364:Pharmaceutical Preparations; D047392:beta-Cyclodextrins; C441457:carboxymethyl-beta-cyclodextrin; D000432:Methanol
keywords: Cyclodextrin; Enantiomer migration order; Enantioseparation; Nonaqueous capillary electrophoresis; Single isomer