title: Determination of enantiomerization barrier of thioridazine by dynamic capillary electrophoresis using sulfated cyclodextrins as chiral selectors.
abstract: The enantiomerization of thioridazine (THD) using sulfated beta-CDs (S-beta-CDs) as chiral selectors in a citrate buffer at pH 3.0 was investigated by dynamic CE. The enantiomers of THD were well separated with dual CD systems consisting of S-beta-CD and a neutral CD. The electropherograms featuring a plateau formation, which indicated the occurrence of the enantiomerization of THD were obtained. The unified equation implemented in the software program DCXplorer was employed to evaluate elution profiles and to determine rate constants of the enantiomerization of THD. Activation parameters were evaluated from temperature-dependent measurements between 15 and 25 degrees C with an increment of 2 degrees C. The enantiomerization barriers of THD in two different electrophoretic systems were determined. Comparative studies on enantioseparation of THD using S-beta-CDs with different degree of substitution and positions of sulfate substituent, such as randomly sulfate-substituted beta-CD, 18-sulfate-substituted beta-CD and heptakis(2,3-dihydroxy-6-O-sulfo)-beta-CD reveal that the interactions between chiral selectors and THD plays an important role in the enantioseparation and enantiomerization of THD.
authors.affiliation: Department of Chemistry, National Taiwan University, Taipei, Taiwan.|Department of Applied Chemistry and Material Science, Fooyin University, Ta-Liao, Kaohsiung County, Taiwan.
authors.forename: Ching-Erh
authors.initials: CE
authors.lastname: Lin
authors.affiliation: Department of Chemistry, National Taiwan University, Taipei, Taiwan.
authors.forename: Ting-Chang
authors.initials: TC
authors.lastname: Ko
authors.affiliation: Department of Chemistry, National Taiwan University, Taipei, Taiwan.
authors.forename: Chia-Ming
authors.initials: CM
authors.lastname: Kuo
authors.affiliation: Organisch-Chemisches Institüt, Ruprecht-Karls-Universität, Heidelberg, Germany.
authors.forename: Oliver
authors.initials: O
authors.lastname: Trapp
authors.affiliation: Department of Chemistry, National Taiwan University, Taipei, Taiwan.
authors.forename: Wann-Yin
authors.initials: WY
authors.lastname: Lin
authors.affiliation: Department of Applied Chemistry and Material Science, Fooyin University, Ta-Liao, Kaohsiung County, Taiwan.
authors.forename: Chen-Hsing
authors.initials: CH
authors.lastname: Lin
authors.affiliation: Department of Chemistry, National Taiwan University, Taipei, Taiwan.
authors.forename: Jong-Chang
authors.initials: JC
authors.lastname: Wu
authors.affiliation: Department of Applied Chemistry and Material Science, Fooyin University, Ta-Liao, Kaohsiung County, Taiwan.
authors.forename: Yu-Chih
authors.initials: YC
authors.lastname: Liu
mesh_terms: D000465:Algorithms; D019075:Electrophoresis, Capillary / Q000379:methods*; D016014:Linear Models; D013237:Stereoisomerism; D013431:Sulfates / Q000737:chemistry*; D013696:Temperature; D013816:Thermodynamics; D013881:Thioridazine / Q000737:chemistry*; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D013431:Sulfates; D047392:beta-Cyclodextrins; D013881:Thioridazine
references.citation: Trapp, O., J. Chromatogr. B 2008, 875, 42-47.
references.citation: Dubsky, P., Svobodova, J., Gas, B., J. Chromatogr. B 2008, 875, 30-34.
references.citation: Dubsky, P., Svobodova, J., Tesarova, E., Gas, B., J. Chromatogr. B 2008, 875, 35-41.
references.citation: Trapp, O., Electrophoresis 2007, 28, 691-696.
references.citation: Trapp, O., Anal. Chem. 2006, 78, 189-198.
references.citation: Trapp, O., Electrophoresis 2006, 27, 534-541.
references.citation: Trapp, O., Electrophoresis 2006, 27, 2999-3006.
references.citation: Trapp, O., Chirality 2006, 18, 489-497.
references.citation: Wistuba, D., Trapp, O., Gel-Moreto, N., Galensa, R., Schurig, V., Anal. Chem. 2006, 78, 3424-3433.
references.citation: Heegaard, N. H. H., Jorgensen, T. J. D., Cheng, L., Schou, C., Nissen, M. H., Trapp, O., Anal. Chem. 2006, 78, 3667-3673.
references.citation: Wolf, C., Chem. Soc. Rev. 2005, 34, 595-608.
references.citation: Krupcik, J., Oswald, P., Majek, P., Sandra, P., Armstrong, D. W., J. Chromatogr. A 2003, 1000, 779-800.
references.citation: Trapp, O., Trapp, G., Schurig, V., Electrophoresis 2004, 25, 318-323.
references.citation: Schoetz, G., Trapp, O., Schurig, V., Electrophoresis 2001, 22, 3185-3190.
references.citation: Trapp, O., Electrophoresis 2005, 26, 487-493.
references.citation: Dubsky, P., Tesarova, E., Gas, B., Electrophoresis 2004, 25, 733-742.
references.citation: Newman, C. I. D., McGuffin, V. L., Electrophoresis 2005, 26, 537-547.
references.citation: Eap, C. B., Koeb, L., Powell, K., Baumann, P., J. Chromatogr. B 1995, 669, 271-279.
references.citation: Patrick, K. S., Singletary, J. L., Chirality 1991, 3, 208-211.
references.citation: Jortani, S. A., Poklis, A., J. Anal. Toxicol. 1993, 17, 374-377.
references.citation: Eap, C. B., Koeb, L., Baumann, P., J. Pharm. Biomed. Anal. 1993, 11, 451-457.
references.citation: Karpinska, J., Sokol, M., J. Trace. Microprobe Techn. 2003, 21, 649-663.
references.citation: de Gaitani, C. M., Martinez, A. S., Bonato, P. S., Electrophoresis 2003, 24, 2723-2730.
references.citation: de Gaitani, C. M., Martinez, A. S., Bonato, P. S., Chirality 2003, 15, 479-485.
references.citation: Lin, C. E., Liao, W. S., Cheng, H. T., Kuo, C. M., Liu, Y. C., Electrophoresis 2005, 26, 3869-3877.
references.citation: Liao, W. S., Lin, C. H., Chen, C. Y., Kuo, C. M., Liu, Y. C., Wu, J. C., Lin, C. E., Electrophoresis 2007, 28, 3922-3929.
references.citation: Lin, C. E., Chen, K. H., J. Chromatogr. A 2001, 930, 155-163.
references.citation: Chankvetadze, B., Kartozia, I., Burjanadze, N., Bergenthal, D., Luftmann, H., Blaschke, G., Chromatographia 2001, 53, S290-S295.
references.citation: Trapp, O., Schoetz, G., Schurig, V., J. Pharm. Biomed. Anal. 2002, 27, 497-505.
references.citation: Gasparrini, F., Pierini, M., Villani, C., De Maria, P., Fontana, A., Ballini, R., J. Org. Chem. 2003, 68, 3173-3177.
references.citation: Cannazza, G., Carrozzo, M. M., Braghiroli, D., Parenti, C., J. Chromatogr B. 2008, 875, 192-199.