Chiral Separation of Bencynonate and Econazole by Cyclodextrin-Modified Capillary Zone Electrophoresis

Dong, Yan; Ren, Xueqin; Huang, Aijin; Sun, Yi; Sun, Ze

doi:10.1002/(sici)1521-4168(19980701)21:7<421::aid-jhrc421>3.0.co;2-v

Cited by 10 publications

(9 citation statements)

References 17 publications

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“…3 shows the electropherograms corresponding to the enantiomeric separation of sulconazole, econazole, and miconazole with HP-b-CD using the CD concentrations that enabled the best enantiomeric resolutions for these compounds. Although the baseline enantiomeric separation of miconazole [37] and econazole [35,38] had previously been performed using this neutral CD, it is the first time that the separation of the enantiomers of sulconazole is achieved using a neutral CD as chiral selector. In fact, in spite of the similitude of its chemical structure with the chemical structure of econazole, the enantiomers of sulconazole had only been separated when a dextrin was used as chiral selector (Rs 1.9) [39].…”

Section: Study Of the Enantioselectivity Through Apparent Analyte-cd mentioning

confidence: 99%

Enantioselective separation of azole compounds by EKC. Reversal of migration order of enantiomers with CD concentration

Castro‐Puyana¹,

Crego²,

Marina³

et al. 2007

Electrophoresis

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The enantioselective separation of a group of six weak base azole compounds was achieved in this work using EKC with three neutral b-CDs as chiral selectors. The native b-CD and two other b-CD derivatives with different types and positions of the substituents on the CD rim ((2-hydroxy)propyl-b-CD (HP-b-CD) and heptakis-2,3,6-tri-O-methyl-b-CD (TM-b-CD)) were employed. Apparent binding constants for each pair compound-CD were determined in order to study analyte-CD interactions. The best enantiomeric resolutions for miconazole, econazole, and sulconazole were observed with HP-b-CD whereas for the separation of the enantiomers of ketoconazole, terconazole, and bifonazole, TM-b-CD was the best chiral selector. The enantioseparations obtained were discussed on the basis of the structure of the compounds taking into account that inclusion into the hydrophobic CD cavity occurred through the phenyl ring closer to the azole group. In addition, a change in the migration order for the enantiomers of two of the compounds studied (ketoconazole and terconazole) with the concentration of HP-b-CD was observed for the first time.

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Section: Study Of the Enantioselectivity Through Apparent Analyte-cd mentioning

confidence: 99%

Enantioselective separation of azole compounds by EKC. Reversal of migration order of enantiomers with CD concentration

Castro‐Puyana¹,

Crego²,

Marina³

et al. 2007

Electrophoresis

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“…It is widely used for the treatment of topical fungal infection and is used as nitrate salt in a variety of pharmaceutical formulations. Several papers have reported the chiral separation of econazole and other antifungal compounds by HPLC [12,13], SFC [14] and CE [15][16][17]. The enantiomeric separation of econazole was obtained using CE with sulfobutyl ether-␤-cyclodextrin (SBE-␤-CD) as chiral buffer modifier [17].…”

Section: Introductionmentioning

confidence: 99%

“…Our separation time in the current CD-MEKC method is ∼8.5 min (∼40% significant time saving) and with no methanol being used as modifier. Chiral separation of econazole was also achieved with the use of 5 mM HP-␤-CD in 50 mM pH 2.5 triethanolamine phosphate buffer with R s 2.0 but no quantitative study of econozale was performed [16]. Enantioselective separation of econazole was also achieved using EKC (R s 2.0) with 2 mM HP-␤-CD in 100 mM phosphate buffer at pH 3.0 [15].…”

Section: Introductionmentioning

confidence: 99%

“…The analysis time obtained was ∼6.5 min. However, the LODs and the analysis of econazole enantiomers on pharmaceutical samples were not discussed in their works [15][16][17]. Quantitative determination of econazole nitrate (pK a = 6.6) in cream formulation by CZE using 20 mM phosphate buffer adjusted to pH 2.5 with phosphoric acid has also been reported with an analysis time of 1.2 min.…”

Section: Introductionmentioning

confidence: 99%

“…It is thus of interest in the present study to develop a CD-MEKC method for the chiral analysis of econazole using HP-␥-CD, a cheaper chiral surfactant than the one previously used i.e. heptakis (2,3,6-tri-O-methyl)-␤-CD (TM-␤-CD) [16] (no chiral recognition of econazole was obtained) and SBE-␤-CD [17]. It is also of interest to compare the performance of HP-␥-CD compared to HP-␤-CD as previously used [16,17] and finally the quantification of econazole in cream formulation of econazole nitrate.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Chiral separation of econazole using micellar electrokinetic chromatography with hydroxypropyl-γ-cyclodextrin

Hermawan

Ibrahim

Sanagi

et al. 2010

Journal of Pharmaceutical and Biomedical Analysis

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Separation of Selected Imidazole Enantiomers Using Dual Cyclodextrin System in Micellar Electrokinetic Chromatography

et al. 2013

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Cyclodextrin-modified micellar electrokinetic chromatography (CD-MEKC) method was developed for simultaneous enantioseparation of three imidazole drugs namely tioconazole, isoconazole and fenticonazole. Three easily available and inexpensive cyclodextrins namely 2-hydroxypropyl-β-cyclodextrin (HP-β-CD), 2-hydroxypropyl-γ-cyclodextrin (HP-γ-CD) and heptakis(2,6-di-O-methyl)-β-cyclodextrin (DM-β-CD) were evaluated to discriminate the six stereoisomers of the drugs. However, none of the three CDs gave a complete enantioseparation of the drugs. Effective enantioseparation of tioconazole, isoconazole and fenticonazole was achieved using a combination of 35 mM HP-γ-CD and 10 mM DM-β-CD as chiral selectors. The best separation using both HP-γ-CD and DM-β-CD (35 mM:10 mM) as chiral selectors were accomplished in background electrolyte (BGE) containing 35 mM phosphate buffer (pH 7.0), 50 mM sodium dodecyl sulfate (SDS) and 15% (v/v) acetonitrile at 27 kV and 30 °C with all peaks resolved in less than 15 min with resolutions, Rs 1.90-27.22 and peak efficiencies, N > 180 000. The developed method was linear over the concentration range of 25-200 mg l(-1) (r(2) > 0.998) and the detection limits (S/N = 3) of the three imidazole drugs were found to be 2.7-7.7 mg l(-1). The CD-MEKC method was successfully applied to the determination of the three imidazole drugs in spiked human urine sample and commercial cream formulation of tioconazole and isoconazole with good recovery (93.6-106.2%) and good RSDs ranging from 2.30-6.8%.

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Chiral Separation of Bencynonate and Econazole by Cyclodextrin-Modified Capillary Zone Electrophoresis

Cited by 10 publications

References 17 publications

Enantioselective separation of azole compounds by EKC. Reversal of migration order of enantiomers with CD concentration

Enantioselective separation of azole compounds by EKC. Reversal of migration order of enantiomers with CD concentration

Chiral separation of econazole using micellar electrokinetic chromatography with hydroxypropyl-γ-cyclodextrin

Separation of Selected Imidazole Enantiomers Using Dual Cyclodextrin System in Micellar Electrokinetic Chromatography

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