Effect of molecular structure of tartrates on chiral recognition of tartrate–boric acid complex chiral selectors in chiral microemulsion electrokinetic chromatography

Hu, Shaoqiang; Chen, Yonglei; Zhu, Hua-dong; Shi, Hai-Jun; Yan, Na; Chen, Xingguo

doi:10.1016/j.chroma.2010.06.063

Cited by 31 publications

(20 citation statements)

References 42 publications

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“…Subsequently, the composition of the tartrate-tetraborate selector as well as further factors such as the concentration of the phosphate buffer and organic modifiers were optimized. In a follow-up investigation the tartrate-borate complex of eight L-tartrate based esters and one D-tartrate ester were investigated as chiral selectors [70]. All tartrate-borate complexes proved to be efficient selectors for the separations of β-blockers except for diethyl-L-tartrate and di-nhexyl-L-tartrate, which were inferior.…”

Section: New Chiral Selectors and Mechanistic Modelsmentioning

confidence: 99%

Chiral electromigration techniques in pharmaceutical and biomedical analysis

Scriba

2011

Bioanal Rev

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Capillary electromigration techniques are often considered ideal methods for enantioseparations due to their high separation selectivity and flexibility. Thus, numerous methods employing a chiral selector as pseudostationary phase in a background electrolyte have been developed and applied for the chiral analysis of drugs in bulk ware, pharmaceutical formulations and biological matrices. Furthermore, electromigration techniques have been combined with spectroscopic methods such as nuclear magnetic resonance in order to understand the complexation of analytes by chiral selectors. The present review focuses on recent developments and applications of chiral electromigration techniques in pharmaceutical and biomedical analysis including examples illustrating analyte-selector complex formation or mechanistic studies which have been published between January 2009 and July 2011. Selector-mediated chiral separations clearly dominate while no applications of capillary electrochromatography to pharmaceutical or biomedical analysis have been reported during this period of time.

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Section: New Chiral Selectors and Mechanistic Modelsmentioning

confidence: 99%

Chiral electromigration techniques in pharmaceutical and biomedical analysis

Scriba

2011

Bioanal Rev

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“…Therefore, the real chiral selector is the complex of di-n-butyl D-tartrate and boric acid instead of di-n-butyl D-tartrate itself. This is because di-n-butyl D-tartrate molecule has two adjacent hydroxyl groups able to react with boric acid to produce a complex acid, resulting in the enantioselectivity for the chiral analytes [13][14][15]. The effects of the concentration of di-n-butyl D-tartrate and sodium tetraborate on the migration time (t) and chiral resolution (R s ) was investigated in the range of 0-30 mM (0.8%, w/v) and 0-50 mM, respectively ( Table 2).…”

Section: Choice Of Chiral Selector and Effects Of Di-n-butyl D-tartramentioning

confidence: 99%

“…As di-n-butyl D-tartrate is a low interfacial tension oil, a transparent and stable microemulsion could be prepared without a cosurfactant. So cosurfactant 1-butanol was finally not used in the microemulsion, being the same as in Hu's work [13][14][15], where cationic surfactant TTAB was used.…”

Section: Effects Of Surfactant and Cosurfactantmentioning

confidence: 99%

“…As all these compounds are basic drugs of pKa *9, the increase of buffer pH decreases their degree of ionization to produce positively charged ions, and weakens their electrostatic interaction with negatively charged chiral selector, which is unfavorable for chiral separation. Thus, the proper pH is significant for enantioseparation [13][14][15]. The effect of microemulsion pH from 7.0 to 9.0 on enantioseparation was investigated.…”

Section: Effect Of Buffer Phmentioning

confidence: 99%

“…Due to its poor solubility in water, dialkyltartrate only has ever been used together with boric acid on enantioselective extraction of some b-blockers [11,12] or chiral MEEKC of some b-blockers and structurally related compounds [13][14][15] and chiral nonaqueous capillary electrophoresis (NACE) of some b-blockers and b-agonists [16]. But there is no published paper reporting the enantioseparation using di-n-butyl D-tartrate-boric acid as the chiral selector in MEEKC for the enantioseparation of b-agonists.…”

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confidence: 99%

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Enantioseparation of Three β-Agonists Using Di-n-butyl d-Tartrate-Boric Acid Complex as Chiral Selector by Means of MEEKC

et al. 2012

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In this study, a self-prepared complex chiral selector, di-n-butyl D-tartrate-boric acid complex, by the reaction of di-n-butyl D-tartrate with boric acid in a running buffer was used as a chiral selector for the enantioseparation of three b-agonists including clenbuterol, cycloclenbuterol and tulobuterol by means of microemulsion electrokinetic chromatography (MEEKC). Three b-agonists were successfully enantioseparated using the chiral system, indicating that the di-n-butyl D-tartrate-boric acid complex was a useful chiral selector. The effects of di-nbutyl D-tartrate and sodium tetraborate concentration, surfactant concentration, cosurfactant, phosphate, buffer pH and composition, as well as applied voltage were extensively investigated to achieve a good enantioseparation. The di-n-butyl D-tartrate and sodium tetraborate concentration in the running buffer had great influence on the chiral resolution (R s ). Three b-agonists which could not be separated with only di-n-butyl D-tartrate, obtained good chiral separation using the complex chiral selector; among them, two pairs including clenbuterol and cycloclenbuterol could be baseline resolved in 7 min under optimized experimental conditions of 0.8% (w/v) di-n-butyl D-tartrate, 40 mM sodium tetraborate, 3.0% (w/v) Tween-20 and 60 mM sodium dihydrogen phosphate with 25 kV as running voltage. The results indicated that the method could be used for the enantioseparation of three b-agonists.

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Advances in the enantioseparation of β‐blocker drugs by capillary electromigration techniques

Aturki¹,

D’Orazio²,

Rocco³

et al. 2011

Electrophoresis

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β-Blocker drugs or β-adrenergic blocking agents are an important class of drugs, prescribed with great frequency. They are used for various diseases, particularly for the treatment of cardiac arrhythmias, cardioprotection after myocardial infarction (heart attack), and hypertension. Almost all β-blocker drugs possess one or more stereogenic centers; however; only some of them are administered as single enantiomers. Since both enantiomers can differ in their pharmacological and toxicological properties, enantioselective analytical methods are required not only for pharmacodynamic and pharmacokinetic studies but also for quality control of pharmaceutical preparations with the determination of enantiomeric purity. In addition to the chromatographic tools, in recent years, capillary electromigration techniques (CE, CEC, and MEKC) have been widely used for enantioselective purposes employing a variety of chiral selectors, e.g. CDs, polysaccharides, macrocyclic antibiotics, proteins, chiral ion-paring agents, etc. The high separation efficiency, rapid analysi,s and low consumption of reagents of electromigration methods make them a very attractive alternative to the conventional chromatographic methods. In this review, the development and applications of electrodriven methods for the enantioseparation of β-blocker drugs are reported. The papers concerning this topic, published from January 2000 until December 2010, are summarised here. Particular attention is given to the coupling of chiral CE and CEC methods to MS, as this detector provides high sensitivity and selectivity.

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Effect of molecular structure of tartrates on chiral recognition of tartrate–boric acid complex chiral selectors in chiral microemulsion electrokinetic chromatography

Cited by 31 publications

References 42 publications

Chiral electromigration techniques in pharmaceutical and biomedical analysis

Chiral electromigration techniques in pharmaceutical and biomedical analysis

Enantioseparation of Three β-Agonists Using Di-n-butyl d-Tartrate-Boric Acid Complex as Chiral Selector by Means of MEEKC

Advances in the enantioseparation of β‐blocker drugs by capillary electromigration techniques

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