Enantiomer separation of drugs by capillary electrophoresis using mixtures of β-cyclodextrin sulfate and neutral cyclodextrins

Izumoto, Shin‐ichi; Nishi, Hiroyuki

doi:10.1002/(sici)1522-2683(19990101)20:1<189::aid-elps189>3.0.co;2-7

Cited by 46 publications

(7 citation statements)

References 29 publications

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“…Separation selectivity could be modified by varying both the percent PDDAC and the type and concentration of an IE competing ion added to the BGE and the IE selectivity coefficients calculated from the model correlated well with expected IE behavior. Finally, neutral and charged cyclodextrins (CDs) have been used extensively in CE for enantiomeric separations 13,15,[24][25][26][27][28] by exploiting host-guest complexation between the CD and the chiral analyte 2 . CDs have also been used for nonchiral separations of organic analytes [29][30][31] and also for inorganic anions.…”

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confidence: 99%

“…A wide variety of pseudo-SPs is available and the only prerequisite of the SP is it should be soluble in the BGE. The majority of published work on pseudo-SPs has focused on the use of micelles (anionic, cationic, zwitterionic, neutral) but several other phases have been investigated, including microemulsions, polymers, − vesicles, proteins, resorcarenes, dendrimers, , and cyclodextrins. − In the analysis of anions, additives containing a quaternary ammonium have proven the most popular. Mori et al recently used a diazacrown ether in the separation of a series of aromatic sulfonates and carboxylates through ion-exchange (IE)-type interactions.…”

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confidence: 99%

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Electrokinetic Chromatography Utilizing Two Pseudostationary Phases Providing Ion-Exchange and Hydrophobic Interactions

2002

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The electrokinetic chromatographic separation of a series of inorganic and organic anions was achieved by utilizing an electrolyte system comprising a cationic soluble polymer (poly(diallydimethylammonium chloride, PDDAC) and a neutral beta-cyclodextrin (beta-CD) as pseudostationary phases. The separation mechanism was a combination of electrophoresis, ion-exchange (IE) interactions with PDDAC, and hydrophobic interactions with beta-CD. The extent of each chromatographic interaction was independently variable, allowing for control of the separation selectivity of the system. IE interactions could be varied by changing either the PDDAC concentration or the concentration of a competing ion (e.g., chloride) in the BGE, while the hydrophobic interactions could be varied by changing the concentration of beta-CD. The separation system was very robust, with the reproducibility of the migration times being <0.7% RSD. A mathematical model that predicted the mobilities of analytes under varying experimental conditions was derived and was shown to give good correlation (r2 = 0.9804) between predicted and experimental migration times. Parameters derived from the model were in good agreement with the ion-exchange and hydrophobic characteristics of the analytes. The model was also applied successfully to the optimization of conditions for the separation of a mixture of analytes or for conditions under which particular analytes migrated in a desired order. That is, the opportunity to tune the separation selectivity has been demonstrated.

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confidence: 99%

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Electrokinetic Chromatography Utilizing Two Pseudostationary Phases Providing Ion-Exchange and Hydrophobic Interactions

2002

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“…Many others bases produced broad peaks that reflect some selectivity while not much distortion in peak shape was seen for the acidic and neutral compounds. We conclude that here SBE-b-CD acts only as a carrier of the non- Actually, very few successful separations based on this type of dual system were reported in the literature [13,15,43].…”

Section: Dual Buffer Systemmentioning

confidence: 84%

“…Thus, other than hydrophobic inclusion of the enantiomer to the CD cavity, there are other interactions between the selector and the analyte, including hydrophilic, polar and electrostatic interactions. In addition to using single chiral selectors to achieve enantioseparation, many groups have demonstrated that mixing two or more chiral selectors together can improve the resolution and offer more flexibility [13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Combinatorial enantiomeric separation of diverse compounds using capillary array electrophoresis

Zhong

Yeung

2002

Electrophoresis

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Combinatorial chiral separations were performed on a 96-capillary array electrophoresis system. A comprehensive enantioseparation protocol employing neutral and sulfated cyclodextrins as chiral selectors for common basic, neutral and acidic compounds was developed. By using only four judiciously chosen separation buffers, successful enantioseparations were achieved for 49 out of 54 test compounds spanning a large variety of pK and structures. Therefore, unknown compounds can be screened in this manner to identify the optimal enantioselective conditions in just one run.

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“…11,13,14 During the last few years, several papers have appeared in the literature reporting the separation of chiral drugs using sulfated β-CD as chiral selector under aqueous [13][14][15][16][17][18] or non-aqueous conditions. The complexation constants are primarily determined by the size, geometry, hydrophobicity, and hydrogen-bonding properties of the analytes.…”

Section: Introductionmentioning

confidence: 99%

CHIRAL CAPILLARY ELECTROPHORETIC SEPARATION OF SELECTED DRUGS AND METABOLITES USING SULFATED Β-Cyclodextrin

Bonato

Jabor

Paias

et al. 2001

Journal of Liquid Chromatography & Related Technologies

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In this paper, we report the chiral separation of some drugs and their metabolites using sulfated β-cyclodextrin, a powerful chiral selector that has proven to be highly efficient for the separation of chiral drugs, alone or in combination, with other chiral additives. Praziquantel, its metabolite trans-4-hydroxypraziquantel, and albendazole sulfoxide are neutral compounds and could be separated at basic pH (8-10).The simultaneous chiral separation of praziquantel and its metabolite enantiomers was only possible by the addition of sodium deoxycholate to the running buffer. Fluoxetine, disopyramide, and mexiletine, as well as their metabolites are basic com-pounds and were separated by appropriate selection of the running buffer pH and CD concentration. In addition, the effects of the experimental parameters, such as concentration of sulfated βcyclodextrin, pH and buffer concentration, temperature, and voltage were also evaluated.Among the several parameters studied, the concentration of the chiral selector and the pH were the most important to obtain the chiral separation of the selected drugs and metabolites.

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Enantiomer separation of drugs by capillary electrophoresis using mixtures of β-cyclodextrin sulfate and neutral cyclodextrins

Cited by 46 publications

References 29 publications

Electrokinetic Chromatography Utilizing Two Pseudostationary Phases Providing Ion-Exchange and Hydrophobic Interactions

Electrokinetic Chromatography Utilizing Two Pseudostationary Phases Providing Ion-Exchange and Hydrophobic Interactions

Combinatorial enantiomeric separation of diverse compounds using capillary array electrophoresis

CHIRAL CAPILLARY ELECTROPHORETIC SEPARATION OF SELECTED DRUGS AND METABOLITES USING SULFATED Β-Cyclodextrin

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