Separation and migration behavior of structurally related phenothiazines in cyclodextrin-modified capillary zone electrophoresis

Chen, Kuo-Hsing; Lin, Chin‐Feng; Liao, Wei‐Ssu; Lin, Wann‐Yin; Hsiao, Yu-You

doi:10.1016/s0021-9673(02)01501-7

Cited by 41 publications

(32 citation statements)

References 28 publications

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“…As MI-S-b-CD is composed of a number of randomly sulfate-substituted b-CDs (typically with substitution of 7-11 mol/mol b-CD), the concentration of MI-S-b-CD is presented by weight percentage (% w/v), instead of mM. In the low pH environment, phenothiazines are entirely protonated and are positively charged [54,56]. However, the CD complexes of phenothiazines become negatively charged upon complexation with MI-S-b-CD.…”

Section: Mobility Calculationsmentioning

confidence: 99%

“…The trends in the variations of the electrophoretic mobility of the enantiomers of phenothiazines as a function of b-CD concentration in this dual CD system are similar to those observed with HP-b-CD/MI-S-b-CD system, but the electrophoretic mobility varies to a greater extent with b-CD/MI-S-b-CD system than with HP-b-CD/MI-S-b-CD system. This is because the binding strength of phenothiazines to b-CD is stronger than that of phenothiazines to HP-b-CD [52,54].…”

Section: â-Cd/mi-s-â-cdmentioning

confidence: 99%

“…Figure 8 shows the variations of the electrophoretic mobility of phenothiazines as a function of g-CD concentration in the range 0-18.0 mM in the presence of 0.75% w/v MI-S-b-CD using a citrate BGE (100 mM) at pH 3.0. As the binding strength of phenothiazines to g-CD is much weaker than that to HP-b-CD, addition of g-CD at a much higher concentration than 0.25 mM is necessary for an effective enantioseparation of phenothiazines [52,54]. As can be seen, the trends in the variations of the electrophoretic mobility of the enantiomers of phenothiazines as a function of g-CD concentration with this dual CD system at pH 3.0 are similar to those observed with HP-b-CD/MI-S-b-CD and b-CD/MI-S-b-CD systems.…”

Section: â-Cd/mi-s-â-cdmentioning

confidence: 99%

“…The interaction of phenothiazines with CDs was found to increase in the order g-CD , HP-b-CD , b-CD [52]. Binding constants of chiral phenothiazines to b-CD and to HP-b-CD in a phosphate buffer were evaluated [54]. Moreover, chiral separations of the enantiomers of thioridazine, trimeprazine, and ethopropazine in nonaqueous CD-modified CZE were also studied [50].…”

Section: Introductionmentioning

confidence: 99%

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Enantioseparation of phenothiazines in cyclodextrin-modified capillary zone electrophoresis using sulfated cyclodextrins as chiral selectors

et al. 2005

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In this study, enantioseparations of five phenothiazines, including promethazine, ethopropazine, trimeprazine, methotrimeprazine, and thioridazine, in CD-modified CZE using dual CD systems consisting of randomly sulfate-substituted CD (MI-S-beta-CD) and a neutral CD as chiral selectors in a citrate buffer (100 mM) at pH 3.0 were investigated. The results indicate that MI-S-beta-CD is an excellent chiral selector for enantioseparation of ethopropazine. The enantiomers of promethazine can also be baseline-resolved with MI-S-beta-CD at concentrations in the range of 0.5-1.0% w/v. On the other hand, thioridazine and trimeprazine interact strongly with neutral CDs. As a result, the enantioselectivity of these two phenothiazines is remarkably and synergistically enhanced with increasing the concentration of neutral CDs in the presence of MI-S-beta-CD and simultaneous enantioseparations of these phenothiazines, except for methotrimeprazine, could favorably be achieved with the use of dual CD systems. Moreover, by varying the concentration of beta-CD or gamma-CD at a fixed concentration of MI-S-beta-CD (0.75% w/v) reversal of the enantiomer migration order of promethazine occurred. This may be attributable to the opposite effects of charged and neutral CDs on the mobility of the enantiomers of promethazine.

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Section: Mobility Calculationsmentioning

confidence: 99%

Section: â-Cd/mi-s-â-cdmentioning

confidence: 99%

Section: â-Cd/mi-s-â-cdmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Enantioseparation of phenothiazines in cyclodextrin-modified capillary zone electrophoresis using sulfated cyclodextrins as chiral selectors

et al. 2005

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“…Enantioseparations of phenothiazines with g-CD as a chiral selector using citrate and phosphate buffer electrolytes at pH 3.0 were reported [53]. Binding constants of chiral phenothiazines to b-CD and to HP-b-CD in a phosphate buffer were evaluated [52]. Moreover, chiral separations of the enantiomers of thioridazine, trimeprazine, and ethopropazine in nonaqueous CD-modified CZE were also studied [48].…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of phenothiazines in CD‐modified CZE using single isomer sulfated CD as a chiral selector

et al. 2007

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Enantioseparations of five chiral phenothiazines in CD-modified CZE using the single isomer sulfate-substituted beta-CD (heptakis(2,3-dihydroxy-6-O-sulfo)-beta-CD, SI-S-beta-CD) and dual CD systems consisting of SI-S-beta-CD and a neutral CD as chiral selectors in a citrate buffer at pH 3.0 were investigated. The results indicate that SI-S-beta-CD is an excellent chiral selector for enantioseparation of promethazine. The enantiomers of trimeprazine were well separated, while those of ethopropazine could also be baseline-resolved with SI-S-beta-CD. With dual CD systems, especially with hydroxypropyl-beta-CD (HP-beta-CD) as neutral CD, the enantioselectivity of thioridazine and ethopropazine was considerably enhanced. Effective enantioseparation of phenothiazines, except for methotrimeprazine, could thus be favorably and simultaneously achieved. Moreover, reversal of the enantiomer migration order of ethopropazine and thioridazine occurred by varying the concentration of gamma-CD in the presence of SI-S-beta-CD. These phenomena may be attributable to the opposite effects of sulfated beta-CD and gamma-CD on the mobility of the enantiomers of ethopropazine and of thioridazine. Comparative studies on the enantioseparations of phenothiazines with single CD and dual CD systems containing SI-S-beta-CD and randomly sulfate-substituted beta-CD (MI-S-beta-CD) were made.

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Characterizing the interaction between enantiomers of eight psychoactive drugs and highly sulfated‐β‐cyclodextrin by counter‐current capillary electrophoresis

Asensi-Bernardi

Escuder-Gilabert

Martı́n-Biosca

et al. 2013

Biomedical Chromatography

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The estimation of apparent binding constants and limit mobilities of the complexes of the enantiomers that characterize the interaction of enantiomers with chiral selectors, in this case highly sulfated β-cyclodextrin, was approached using a simple and economic electrophoretic modality, the complete filling technique (CFT) in counter-current mode. The enantiomers of eight psychoactive drugs, four antihistamines (dimethindene, promethazine, orphenadrine and terfenadine) and four antidepressants (bupropion, fluoxetine, nomifensine and viloxazine) were separated for the first time for this cyclodextrin (CD). Estimations of thermodynamic and electrophoretic enantioselectivies were also performed. Results indicate that, in general, thermodynamic enantioselectivity is the main component explaining the high resolution found, but also one case suggests that electrophoretic enantioselectivity itself is enough to obtain a satisfactory resolution. CFT results advantageous compared with conventional capillary electrophoresis (CE) and partial filling technique (PFT) for the study of the interaction between drugs and chiral selectors. It combines the use of a simple fitting model (as in CE), when the enantiomers do not exit the chiral selector plug during the separation (i.e. mobility of electroosmotic flow larger than mobility of CD), and drastic reduction of the consumption (and cost; ~99.7%) of the CD reagent (as in PFT) compared with the conventional CE.

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Separation and migration behavior of structurally related phenothiazines in cyclodextrin-modified capillary zone electrophoresis

Cited by 41 publications

References 28 publications

Enantioseparation of phenothiazines in cyclodextrin-modified capillary zone electrophoresis using sulfated cyclodextrins as chiral selectors

Enantioseparation of phenothiazines in cyclodextrin-modified capillary zone electrophoresis using sulfated cyclodextrins as chiral selectors

Enantioseparation of phenothiazines in CD‐modified CZE using single isomer sulfated CD as a chiral selector

Characterizing the interaction between enantiomers of eight psychoactive drugs and highly sulfated‐β‐cyclodextrin by counter‐current capillary electrophoresis

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