Enantioseparation of Chiral Antimycotic Drugs by HPLC with Polysaccharide-Based Chiral Columns and Polar Organic Mobile Phases with Emphasis on Enantiomer Elution Order

Mskhiladze, Antonina; Karchkhadze, M.; Dadianidze, Alexandre; Fanali, Salvatore; Farkas, Tamás; Chankvetadze, Bezhan

doi:10.1007/s10337-013-2396-8

Cited by 31 publications

(20 citation statements)

References 36 publications

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“…As summarized in Table 3, 11 out of the 13 analytes could be baseline resolved, and only two analytes of itraconazole and flutrimazole were partially resolved. In particular, butoconazole enantiomers were well separated on this column using the n-hexane/EtOH 92/8 mobile phase with a resolution as high as 13.57. It should be noted that Chiralpak IC showed enantioselectivity for two analytes (ornidazole and flutrimazole) that were not resolved by the other CSPs.…”

Section: Chiral Separation On Chiralpak Icmentioning

confidence: 99%

“…From the 15 analytes separated in this paper, the chiral separations of sertaconazole, butoconazole, flutrimazole, and intermediate are reported for the first time. In cases of other 11 analytes, their enantioseparations have been published using HPLC , supercritical fluid chromatography or CE . In these reports, a wide range of polysaccharide‐based CSPs have been used for enantiomeric resolution in HPLC.…”

Section: Introductionmentioning

confidence: 99%

“…And Mskhiladze et al. were devoted to the investigation of enantiomer migration order of ten chiral antifungals on six Lux amylose/cellulose columns under polar organic mobile phase. It can be concluded that coated polysaccharide‐derived CSPs have been applied in majority of study, while the immobilized ones are seldom reported for enantioseparation of these azole analytes.…”

Section: Introductionmentioning

confidence: 99%

“…Chankvetadze et al [18] used four different polysaccharide-type CSPs (Chiralpak AD, Chiralcel OD, Chiralcel OJ, and synthesized CDCPC) for comparative enantioseparation of enilconazole, miconazole, and sulconazole. And Mskhiladze et al [13] were devoted to the investigation of enantiomer migration order of ten chiral antifungals on six Lux amylose/cellulose columns under polar organic mobile phase. It can be concluded that coated polysaccharide-derived CSPs have been applied in majority of study, while the immobilized ones are seldom reported for enantioseparation of these azole analytes.…”

Section: Introductionmentioning

confidence: 99%

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Comparative studies of immobilized chiral stationary phases based on polysaccharide derivatives for enantiomeric separation of 15 azole compounds

et al. 2018

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Immobilized polysaccharide-based columns showed excellent enantioselectivity in normal phase separation mode. In this work, enantioseparation abilities of four immobilized polysaccharide-derived chiral stationary phases (Chiralpak IA, Chiralpak IB, Chiralpak IC, and Chiralpak ID) toward 15 azole compounds were evaluated. Separation was carried out using n-hexane as mobile phase with ethanol, 1-propanol, 1-butanol, and 2-propanol as modifiers. And twelve compounds have achieved baseline separation with the resolutions ranging between 2.05 and 21.73. The enantioseparation on the four polysaccharide-based chiral columns using different alcohol modifiers was compared. In general, the best separation performance was identified as Chiralpak IC, which was able to resolve 11 compounds to baseline and two partially under the screening conditions. Separation on Chiralpak IB was not satisfactory, because only four compounds were baseline separated.

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Section: Chiral Separation On Chiralpak Icmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Comparative studies of immobilized chiral stationary phases based on polysaccharide derivatives for enantiomeric separation of 15 azole compounds

et al. 2018

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“…Therefore, chiral recognition and the separation of KTZ enantiomers is of vital importance in research and in production. The enantio-separation of ketoconazole was achieved by using the commercially available chiral column or electrophoresis method (Bernal et al, 2000;Toribio et al, 2001;Castro-Puyana et al, 2006;Mskhiladze et al, 2013). However, the separation of KTZ enantiomers by HPLC with chiral mobile phase additive has not previously been reported.…”

Section: Introductionmentioning

confidence: 99%

Resolution of ketoconazole enantiomers by high-performance liquid chromatography and inclusion complex formation between selector and enantiomers

Sun

Chen

et al. 2015

Chemical Papers

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The analytical resolution of ketoconazole (KTZ) enantiomers was performed by high-performance liquid chromatography with sulphobutylether-β-cyclodextrin (SBE-β-CD) as a chiral mobile phase additive (chiral selector). Some important factors affecting the resolution of KTZ enantiomers were investigated. In addition, the molecular interaction between KTZ and SBE-β-CD was studied using the UV absorption spectrum and HPLC for an understanding of the resolution process. The results show that the type and concentration of the chiral mobile phase additive, the pH of the mobile phase and the volume fraction of methanol (φMeOH) in the mobile phase all have a clear influence on the resolution of KTZ enantiomers. Under optimal conditions, namely the use of 0.5 mmol L −1 SBE-β-CD as the chiral mobile phase additive, pH of 4.0 and φMeOH in the mobile phase of 0.6, KTZ enantiomers are resolved with a resolution of 3.74. SBE-β-CD can bind to KTZ with a stability constant of 1157. The chromatographic method can provide the complexation stability constants of (+)-KTZ with SBE-β-CD (K (+) ) and (-)-KTZ with SBE-β-CD (K (−) ). The intrinsic enantioselectivity was calculated from the K (+) to K (−) ratio as 1.34.

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Enantioseparation of selected chiral sulfoxides in high-performance liquid chromatography with polysaccharide-based chiral selectors in polar organic mobile phases with emphasis on enantiomer elution order

Gegenava

Chankvetadze

Farkas³

et al. 2014

J. Sep. Science

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The separation of the enantiomers of 17 chiral sulfoxides was studied on polysaccharide-based chiral columns in polar organic mobile phases. Enantiomer elution order (EEO) was the primary objective in this study. Two of the six chiral columns, especially those based on amylose tris(3,5-dimethylphenylcarbamate) and cellulose tris(4-chloro-3-methylphenylcarbamate) (Lux Cellulose-4) proved to be most successful in the separation of the enantiomers of the studied sulfoxides. Interesting examples of EEO reversal were observed depending on the chiral selector or the composition of the mobile phase. For instance, the R-(+) enantiomer of lansoprazole eluted before the S-(-) enantiomer on Lux Cellulose-1 in both methanol or ethanol as the mobile phase, while the elution order was opposite in the same eluents on amylose tris(3,5-dimethylphenylcarbamate) with the S-(-) enantiomer eluting before the R-(+) enantiomer. The R-(+) enantiomer of omeprazole eluted first on Lux Amylose-2 in methanol but it was second when acetonitrile was used as the mobile phase with the same chiral selector. Several other examples of reversal in EEO were observed in this study. An interesting example of the separation of four stereoisomers of phenaminophos sulfoxide containing chiral sulfur and phosphor atoms is also reported here.

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Enantioseparation of Chiral Antimycotic Drugs by HPLC with Polysaccharide-Based Chiral Columns and Polar Organic Mobile Phases with Emphasis on Enantiomer Elution Order

Cited by 31 publications

References 36 publications

Comparative studies of immobilized chiral stationary phases based on polysaccharide derivatives for enantiomeric separation of 15 azole compounds

Comparative studies of immobilized chiral stationary phases based on polysaccharide derivatives for enantiomeric separation of 15 azole compounds

Resolution of ketoconazole enantiomers by high-performance liquid chromatography and inclusion complex formation between selector and enantiomers

Enantioseparation of selected chiral sulfoxides in high-performance liquid chromatography with polysaccharide-based chiral selectors in polar organic mobile phases with emphasis on enantiomer elution order

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