Enantiomeric separation of basic compounds usin heptakis(2,3-di-O-methyl-6-O-sulfo)-β-cyclodextrin in combination with potassium camphorsulfonate in nonaqueous capillary electrophoresis:: Optimization by means of an experimental design

被引:47
作者
Servais, AC
Fillet, M
Chiap, P
Dewé, W
Hubert, P
Crommen, J [1 ]
机构
[1] Univ Liege, Inst Pharm, Dept Analyt Pharmaceut Chem, B-4000 Liege 1, Belgium
[2] Stat & Math Sci, Lilly Dev Ctr, Mont St Guibert, Belgium
关键词
basic drugs; cyclodextrin; ion-pairing reagent; nonaqueous capillary electrophoresis;
D O I
10.1002/elps.200405962
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
The enantiomeric separation of a series of basic pharmaceuticals (beta-blockers, local anesthetics, sympathomimetics) has been investigated in nonaqueous capillary electrophoresis (NACE) systems using heptakis(2,3-di-O-methyl-6-O-sulfo)-beta-cyclodextrin (HDMS-P-CD) in combination with potassium camphorsulfonate (camphorSO(3)(-)). For this purpose, a face-centered central composite design with 11 experimental points was applied. The effect of the concentrations of HDMS-beta-CD and camphorSO(3)(-) on enantioresolution was statistically evaluated and depended largely on the considered analyte. The presence of camphorSO(3)(-) was found to be particularly useful for the enantioseparation of compounds with high affinity for the anionic CD. CamphorSO(3)(-) seems to act as a competitor, reducing the affinity for the CD, probably by ion-pair formation with these analytes. For compounds with lower affinity for HDMS-beta-CD, the combination of camphorSO(3)(-) and the CD appeared to have a favorable effect on enantioresolution only if the optimal CD concentration could be reached. On the other hand, for compounds characterized by a very low affinity for the anionic CD, the association of camphorSO(3)(-) and HDMS-beta-CD is always unfavorable. Finally, experimental conditions were selected by means of the multivariate approach in order to obtain the highest resolution (R-s) value for each studied compound.
引用
收藏
页码:2701 / 2710
页数:10
相关论文
共 36 条
[1]  
Amini A, 2001, ELECTROPHORESIS, V22, P3107, DOI 10.1002/1522-2683(200109)22:15<3107::AID-ELPS3107>3.0.CO
[2]  
2-Z
[3]   CHIRAL SEPARATION OF BASIC DRUGS BY CAPILLARY ZONE ELECTROPHORESIS WITH CYCLODEXTRIN ADDITIVES [J].
BECHET, I ;
PAQUES, P ;
FILLET, M ;
HUBERT, P ;
CROMMEN, J .
ELECTROPHORESIS, 1994, 15 (06) :818-823
[4]   Chiral separation in non-aqueous media by capillary electrophoresis using the ion-pair principle [J].
Bjornsdottir, I ;
Hansen, SH ;
Terabe, S .
JOURNAL OF CHROMATOGRAPHY A, 1996, 745 (1-2) :37-44
[5]  
Busby MB, 2002, ELECTROPHORESIS, V23, P456, DOI 10.1002/1522-2683(200202)23:3<456::AID-ELPS456>3.0.CO
[6]  
2-X
[7]   Capillary electrophoretic separation of weak base enantiomers using the single-isomer heptakis-(2,3-dimethyl-6-sulfato)-β-cyclodextrin as resolving agent and methanol as background electrolyte solvent [J].
Cai, H ;
Vigh, G .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 1998, 18 (4-5) :615-621
[8]   Non-aqueous capillary electrophoretic separation of enantiomeric amines with (-)-2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid as chiral counter ion [J].
Carlsson, Y ;
Hedeland, M ;
Bondesson, U ;
Pettersson, C .
JOURNAL OF CHROMATOGRAPHY A, 2001, 922 (1-2) :303-311
[9]   Recent trends in enantioseparations using capillary electromigration techniques [J].
Chankvetadze, B .
TRAC-TRENDS IN ANALYTICAL CHEMISTRY, 1999, 18 (07) :485-498
[10]   ABOUT SOME ASPECTS OF THE USE OF CHARGED CYCLODEXTRINS FOR CAPILLARY ELECTROPHORESIS ENANTIOSEPARATION [J].
CHANKVETADZE, B ;
ENDRESZ, G ;
BLASCHKE, G .
ELECTROPHORESIS, 1994, 15 (06) :804-807