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Enantioseparation of novel COX‐2 anti‐ inflammatory drugs by capillary electrophoresis using single and dual cyclodextrin systems
Author(s) -
Calvet Carmen,
Cuberes Rosa,
PérezMaseda Carlos,
Frigola Jordi
Publication year - 2002
Publication title -
electrophoresis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.666
H-Index - 158
eISSN - 1522-2683
pISSN - 0173-0835
DOI - 10.1002/1522-2683(200206)23:11<1702::aid-elps1702>3.0.co;2-#
Subject(s) - capillary electrophoresis , cyclodextrin , chromatography , chemistry , dual (grammatical number) , capillary action , materials science , art , literature , composite material
A capillary electrophoresis method was developed for the enantioseparation of three novel cyclooxygenase‐2 (COX‐2) inhibitor drugs (E‐6259, E‐6036 and E‐6087) with anti‐inflammatory and analgesic activities using sulfobutyl ether‐β‐cyclodextrin (SBE‐β‐CD) as a chiral selector. The use of 50 m M sodium tetraborate at pH 9.2 with 30% v/v methanol, containing 7.1 m M SBE‐β‐CD, as a background electrolyte (BGE) allowed the complete enantioseparation of the three neutral racemic mixtures (resolution = 2.4, 3.0 and 8.7, respectively) and their corresponding metabolites (oxidation products) in a single run. Migration times were shortened with some loss of enantioresolution by adding 1.75 m M dimethyl‐β‐cyclodextrin (DM‐β‐CD) to the previous BGE (dual CD system). The reversal of the migration order of E‐6259 enantiomers in the dual CD system was also studied. Furthermore, the addition of DM‐β‐CD to the BGE introduced a new chemoselectivity in the system that allowed E‐6259 to be separated from the structurally similar compound E‐6036.