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Octakis‐6‐sulfato‐γ‐cyclodextrin as additive for capillary electrokinetic chromatography of dibenzoazepines: Carbamazepine, oxcarbamazepine and their metabolites
Author(s) -
Marziali Ettore,
Raggi Maria Augusta,
Komarova Natalja,
Kenndler Ernst
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(200209)23:17<3020::aid-elps3020>3.0.co;2-#
Subject(s) - chromatography , carbamazepine , chemistry , cyclodextrin , electrokinetic phenomena , medicine , epilepsy , psychiatry
Single isomer octakis‐(2,3‐dihydroxy‐)6‐sulfato‐γ‐cyclodextrin used as pseudostationary phase of the background electrolyte interacts with dibenzo[ b , f ]azepines (consisting of a condensed 3‐ring system) and forms negatively charged complexes. Hydroxygroups in position 2 and 3 at carbamazepine increase the extent of interaction, whereas substitution by oxygen at position 10 and/or 11 reduces it. The complex constants for the analytes are ranging from few tens L/mol (10‐hydroxycarbamazepine, 10,11‐dihydroxycarbamazepine, 10,11‐epoxycarbamazepine, oxcarbazepine) to several hundreds L/mol (carbamazepine, 2‐hydroxycarbamazepine, 3‐hydroxycarbamazepine), and are much larger than those of the analytes with octakis‐(2,3‐dimethyl‐)‐6‐sulfato‐γ‐cyclodextrin. Full enantiomeric separation of the chiral metabolites of carbamazepine and oxcarbazepine is obtained at octakis‐(2,3‐dihydroxy‐)‐6‐sulfato‐γ‐cyclodextrin concentrations of about 10 m M (3 m M borate buffer, pH 8.5). Compared to heptakis‐6‐sulfato‐β‐cyclodextrin, selectivity differs and stereoselectivity is more pronounced.