title: Enantiomeric separation of tapentadol by capillary electrophoresis--study of chiral selectivity manipulation by various types of cyclodextrins.
abstract: The chiral recognition of the centrally acting analgesic agent tapentadol and its isomers with various cyclodextrins (CDs) was studied by capillary electrophoresis, focusing on the migration order of four stereoisomers. In the case of non-charged hydroxypropylated CDs (2-hydroxypropyl-β-CD, 2-hydroxypropyl-γ-CD) the beta derivative was able to discriminate the S,R- and R,S-isomers in acidic background electrolyte, whereas the gamma allowed the separation of S,S- and R,R-tapentadol, respectively. Dual CD system containing both hosts was used to separate all of four isomers. Negatively charged sulfated-α-CD at 1.0% (w/v) concentration in 100mM sodium borate buffer (pH 9.5) was capable of separating the isomers with favorable enantiomer migration order and the optimized method was able to determine 0.15% of chiral impurities of tapentadol in the presence of the last migrating clinically important R,R-isomer.
authors.affiliation: Regional Centre of Advanced Materials and Technology, Department of Analytical Chemistry, Faculty of Science, Palacký University in Olomouc, 17. listopadu 12, Olomouc CZ-77146, Czech Republic.
authors.forename: Joanna
authors.initials: J
authors.lastname: Znaleziona
authors.affiliation: Department of Pharmaceutical Chemistry, Semmelweis University, H-1092 Hőgyes Endre u. 9. Budapest, Hungary.
authors.forename: Ida
authors.initials: I
authors.lastname: Fejős
authors.affiliation: Department of Analytical Chemistry, Faculty of Science, Palacký University in Olomouc, 17. listopadu 12, Olomouc CZ-77146, Czech Republic.
authors.forename: Juraj
authors.initials: J
authors.lastname: Ševčík
authors.affiliation: Zentiva, k.s., U Kabelovny, Prague, Czech Republic.
authors.forename: Michal
authors.initials: M
authors.lastname: Douša
authors.affiliation: Department of Pharmaceutical Chemistry, Semmelweis University, H-1092 Hőgyes Endre u. 9. Budapest, Hungary; Department of Pharmacognosy, Semmelweis University, H-1085 Üllői út 26. Budapest, Hungary.
authors.forename: Szabolcs
authors.initials: S
authors.lastname: Béni
authors.affiliation: Regional Centre of Advanced Materials and Technology, Department of Analytical Chemistry, Faculty of Science, Palacký University in Olomouc, 17. listopadu 12, Olomouc CZ-77146, Czech Republic. Electronic address: vitezslav.maier@upol.cz.
authors.forename: Vítězslav
authors.initials: V
authors.lastname: Maier
mesh_terms: D000700:Analgesics / Q000032:analysis* / Q000737:chemistry; D003505:Cyclodextrins / Q000737:chemistry*; D019075:Electrophoresis, Capillary / Q000379:methods*; D015394:Molecular Structure; D010636:Phenols / Q000032:analysis* / Q000737:chemistry; D013237:Stereoisomerism; D000077432:Tapentadol
chemical_list: D000700:Analgesics; D003505:Cyclodextrins; D010636:Phenols; D000077432:Tapentadol
keywords: Capillary electrophoresis; Chiral separation; Cyclodextrin; Migration order; Nucynta; Tapentadol