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

Enantioseparations of five chiral phenothiazines in CD‐modified CZE using the single isomer sulfate‐substituted β‐CD (heptakis(2,3‐dihydroxy‐6‐O‐sulfo)‐β‐CD, SI‐S‐β‐CD) and dual CD systems consisting of SI‐S‐β‐CD and a neutral CD as chiral selectors in a citrate buffer at pH 3.0 were investigated. The results indicate that SI‐S‐β‐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‐β‐CD. With dual CD systems, especially with hydroxypropyl‐β‐CD (HP‐β‐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 γ‐CD in the presence of SI‐S‐β‐CD. These phenomena may be attributable to the opposite effects of sulfated β‐CD and γ‐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‐β‐CD and randomly sulfate‐substituted β‐CD (MI‐S‐β‐CD) were made.

[1]  J. Bosque-Sendra,et al.  Determination of phenothiazines in pharmaceutical formulations and human urine using capillary electrophoresis with chemiluminescence detection , 2006, Electrophoresis.

[2]  Pham Thi Thanh Ha,et al.  Recent advances in pharmaceutical applications of chiral capillary electrophoresis. , 2006, Journal of pharmaceutical and biomedical analysis.

[3]  C. Kuo,et al.  Enantioseparation of phenothiazines in cyclodextrin‐modified capillary zone electrophoresis using sulfated cyclodextrins as chiral selectors , 2005, Electrophoresis.

[4]  J. Bosque-Sendra,et al.  Development and validation of a capillary electrophoresis method for the determination of phenothiazines in human urine in the low nanogram per milliliter concentration range using field‐amplified sample injection , 2005, Electrophoresis.

[5]  Ana M. García-Campaña,et al.  Determination of thiazinamium, promazine and promethazine in pharmaceutical formulations using a CZE method , 2005 .

[6]  M. Schmid,et al.  Recent advances in chiral separation principles in capillary electrophoresis and capillary electrochromatography , 2004, Electrophoresis.

[7]  Wei‐Ssu Liao,et al.  Enantioseparations of hydrobenzoin and structurally related compounds in capillary zone electrophoresis using heptakis(2,3‐dihydroxy‐6‐O‐sulfo)‐β‐cyclodextrin as chiral selector and enantiomer migration reversal of hydrobenzoin with a dual cyclodextrin system in the presence of borate complexation , 2004, Electrophoresis.

[8]  Wei‐Ssu Liao,et al.  Enantioseparation of benzoins and enantiomer migration reversal of hydrobenzoin in capillary zone electrophoresis with dual cyclodextrin systems and borate complexation. , 2004, Journal of chromatography. A.

[9]  Wei‐Ssu Liao,et al.  Enantioseparation of phenothiazines in cyclodextrin‐modified capillary zone electrophoresis: Reversal of migration order , 2003, Electrophoresis.

[10]  A. Servais,et al.  Enhancement of selectivity and resolution in the enantioseparation of uncharged compounds using mixtures of oppositely charged cyclodextrins in capillary electrophoresis , 2003, Electrophoresis.

[11]  Wei‐Ssu Liao,et al.  Separation and migration behavior of structurally related phenothiazines in cyclodextrin-modified capillary zone electrophoresis. , 2002, Journal of chromatography. A.

[12]  Wei‐Ssu Liao,et al.  Enantioseparation of phenothiazines in cyclodextrin-modified micellar electrokinetic chromatography. , 2002, Journal of chromatography. A.

[13]  M. Fillet,et al.  Prediction of selectivity for enantiomeric separations of uncharged compounds by capillary electrophoresis involving dual cyclodextrin systems. , 2002, Journal of chromatography. A.

[14]  C. E. Lin,et al.  Enantioseparation of phenothiazines in capillary zone electrophoresis using cyclodextrins as chiral selectors. , 2001, Journal of chromatography. A.

[15]  G. Vigh,et al.  Separation selectivity patterns in the capillary electrophoretic separation of anionic enantiomers by octakis‐6‐sulfato‐γ‐cyclodextrin , 2001, Electrophoresis.

[16]  G. Blaschke,et al.  Enantioseparations in capillary electromigration techniques: recent developments and future trends. , 2001, Journal of chromatography. A.

[17]  M. Schmid,et al.  Recent progress in chiral separation principles in capillary electrophoresis , 2000, Electrophoresis.

[18]  T. de Boer,et al.  Recent innovations in the use of charged cyclodextrins in capillary electrophoresis for chiral separations in pharmaceutical analysis , 2000, Electrophoresis.

[19]  S. Fanali,et al.  Enantioselective determination by capillary electrophoresis with cyclodextrins as chiral selectors. , 2000, Journal of chromatography. A.

[20]  M. Fillet,et al.  Enantiomeric separations of drugs using mixtures of charged and neutral cyclodextrins. , 2000, Journal of chromatography. A.

[21]  L. Kremser,et al.  pKa shift‐associated effects in enantioseparations by cyclodextrin‐mediated capillary zone electrophoresis , 1999, Electrophoresis.

[22]  M. Fillet,et al.  Designed combination of chiral selectors for adjustment of enantioseparation selectivity in capillary electrophoresis , 1999, Electrophoresis.

[23]  Y. Ci,et al.  Enantiomeric separation of promethazine and d,l-α-amino-β-[4-(1,2-dihydro-2-oxo-quinoline)] propionic acid drugs by capillary zone electrophoresis using albumin as chiral selectors , 1999 .

[24]  E. Wang,et al.  Separation of promethazine and thioridazine using capillary electrophoresis with end-column amperometric detection. , 1999, Journal of chromatography. B, Biomedical sciences and applications.

[25]  A. Stalcup,et al.  Enantiomeric separations of terbutaline by CE with a sulfated beta-cyclodextrin chiral selector: a quantitative binding study. , 1998, Analytical chemistry.

[26]  G. Scriba,et al.  Electrophoretic stereoisomer separation of aspartyl dipeptides and tripeptides in untreated fused-silica and polyacrylamide-coated capillaries using charged cyclodextrins , 1998 .

[27]  M. Fillet,et al.  Enantioseparation of uncharged compounds by capillary electrophoresis using mixtures of anionic and neutral β-cyclodextrin derivatives , 1998 .

[28]  I. Lurie Separation selectivity in chiral and achiral capillary electrophoresis with mixed cyclodextrins , 1997 .

[29]  B. Chankvetadze Capillary Electrophoresis in Chiral Analysis , 1997 .

[30]  G. Vigh,et al.  A Family of Single-Isomer Chiral Resolving Agents for Capillary Electrophoresis. 2. Hepta-6-sulfato-β-cyclodextrin. , 1997, Analytical chemistry.

[31]  H. Cai,et al.  A Family of Single-Isomer Chiral Resolving Agents for Capillary Electrophoresis. 3. Heptakis(2,3-dimethyl-6-sulfato)-β-cyclodextrin. , 1997, Analytical chemistry.

[32]  S. Wren Mobility measurements on dansylated amino acids , 1997 .

[33]  T. Lindstrom,et al.  Chiral separation of neutral species by capillary electrophoresis evaluation of a theoretical model , 1997 .

[34]  P. Gareil,et al.  Selectivity in capillary electrophoresis:  application to chiral separations with cyclodextrins. , 1997, Analytical chemistry.

[35]  P. Gareil,et al.  Intrinsic selectivity in capillary electrophoresis for chiral separations with dual cyclodextrin systems. , 1997, Analytical chemistry.

[36]  D. Armstrong,et al.  Chiral separation of monoterpenes using mixtures of sulfated β-cyclodextrins and α-cyclodextrin as chiral additives in the reversed-polarity capillary electrophoresis mode , 1997 .

[37]  Fang Wang,et al.  Chiral separations by nonaqueous capillary electrophoresis. , 1996, Analytical chemistry.

[38]  C. Cramers,et al.  Determination of structurally related phenothiazines by capillary zone electrophoresis and micellar electrokinetic chromatography , 1996 .

[39]  G. Blaschke,et al.  Reversal of enantiomer elution order in capillary electrophoresis using charged and neutral cyclodextrins , 1996 .

[40]  K. Gahm,et al.  Application of sulfated cyclodextrins to chiral separations by capillary zone electrophoresis. , 1996, Analytical chemistry.

[41]  R. Wells,et al.  Determination of a cardiac antiarrhythmic, tricyclic antipsychotics and antidepressants in human and animal urine by micellar electrokinetic capillary chromatography using a bile salt. , 1995, Journal of chromatography. B, Biomedical applications.

[42]  M. Sepaniak,et al.  Evaluation of a dual-cyclodextrin phase variant of capillary electrokinetic chromatography for separations of nonionizable solutes , 1995 .

[43]  M. Sepaniak,et al.  Separation of stereoisomers of aminoglutethimide using three capillary electrophoretic techniques , 1995 .

[44]  Robert L. Williams,et al.  Experimental evidence for the existence of duoselective (Type III) enantiomer separations in the capillary electrophoretic analysis of chiral weak acids , 1995 .

[45]  I. Lurie,et al.  Chiral resolution of cationic drugs of forensic interest by capillary electrophoresis with mixtures of neutral and anionic cyclodextrins. , 1994, Analytical chemistry.

[46]  V. Stella,et al.  Sulfobutyl Ether .beta.-Cyclodextrin as a Chiral Discriminator for Use with Capillary Electrophoresis , 1994 .

[47]  James P. Landers,et al.  Handbook of Capillary Electrophoresis , 1993 .

[48]  H. Poppe,et al.  Chiral separations by complexation with proteins in capillary zone electrophoresis , 1993 .

[49]  C. E. Evans,et al.  Comprehensive strategy for chiral separations using sulfated cyclodextrins in capillary electrophoresis. , 2003, Chirality.

[50]  G. Vigh,et al.  A family of single‐isomer, sulfated γ‐cyclodextrin chiral resolving agents for capillary electrophoresis: Octa(6‐O‐sulfo)‐γ‐cyclodextrin , 2003 .

[51]  H. Luftmann,et al.  Enantioseperation of chiral phenothiazine derivatives in capillary electrophoresis using cyclodextrin type chiral selectors , 2001 .

[52]  Rongying Wang,et al.  Separation of phenothiazines in aqueous and non-aqueous capillary electrophoresis , 2000 .

[53]  K. Waldron,et al.  Estimation of the pH‐independent binding constants of alanylphenylalanine and leucylphenylalanine stereoisomers with β‐cyclodextrin in the presence of urea , 1999, Electrophoresis.

[54]  G. Blaschke,et al.  About some aspects of the use of charged cyclodextrins for capillary electrophoresis enantioseparation , 1994, Electrophoresis.