Computer simulation and enantioselective capillary electrophoresis to characterize isomer mixtures of sulfated β-cyclodextrins.

Mikkonen, Saara Lin Katriine; Caslavsky, Jitka; Hruška, Vlastimil; Thormann, Wolfgang (2018). Computer simulation and enantioselective capillary electrophoresis to characterize isomer mixtures of sulfated β-cyclodextrins. Electrophoresis, 39(5-6), pp. 770-778. Wiley-VCH 10.1002/elps.201700376

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The enantiomeric separation of methadone in the presence of multiple isomer mixtures of sulfated β-cyclodextrin (S-β-CD) was studied experimentally with CZE and theoretically using computer simulation. Experiments were performed over many years with several lots of S-β-CD from the same manufacturer with a specified degree of substitution of 7-11. Large differences in the migration patterns were observed between certain lots and it was concluded that the extent of labelling in lots released after a transition time was higher than originally specified. The migration pattern was observed to be associated with (i) the ionic strength increase resulting from using S-β-CDs with a higher charge state and (ii) differences in buffer composition. Apparent binding constants between methadone and the S-β-CD and complex mobilities were determined for different lots of S-β-CD at varying ionic strength using phosphate and 3-morpholino-2-hydroxypropanesulfonic acid buffers. The obtained values were used as input for simulations. For a given ionic strength, agreement between predicted and experimentally observed behavior was obtained for different buffers. R-methadone has a stronger interaction with S-β-CD than S-methadone. For any given configuration there is a distinct S-β-CD concentration range which results in the cationic migration of S-methadone while the migration direction of R-methadone is reversed. This configuration was demonstrated to be applicable for micropreparative CZE separations.

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