High-performance liquid chromatography enantioseparation of proton pump inhibitors using the immobilized amylose-based Chiralpak IA chiral stationary phase in normal-phase, polar organic and reversed-phase conditions

Cirilli, Roberto; Ferretti, Rosella; Gallinella, Bruno; Santis, Emiliana De; Zanitti, Leo; Torre, Francesco La

doi:10.1016/j.chroma.2007.11.027

Cited by 71 publications

(60 citation statements)

References 32 publications

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“…Although several chromatographic methods for the chiral analysis of omeprazole and its analogs have been published yet, [15][16][17][18][19] no information about NMR as a chiral technique for this family of drugs can be found in the literature. This is probably due to the high degradation rate of these compounds in water, which hinders the use of hydrosoluble CSAs like cyclodextrins or chiral organic acids/bases; their low affinity with chiral lanthanide reagents, and the lack of functional groups capable of reacting easily with Mosher reagents.…”

Section: Introductionmentioning

confidence: 99%

Use of (S)‐BINOL as NMR chiral solvating agent for the enantiodiscrimination of omeprazole and its analogs

2009

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The application of (S)-1,1'-binaphthyl-2,2'-diol as NMR chiral solvating agent (CSA) for omeprazole, and three of its analogs (lanso-, panto-, and rabe-prazole) was investigated. The formation of diastereomeric host-guest complexes in solution between the CSA and the racemic substrates produced sufficient NMR signal splitting for the determination of enantiomeric excesses by (1)H- or (19)F-NMR spectroscopy. Using of hydrophobic deuterated solvents was mandatory for obtaining good enantiodiscrimination, thus suggesting the importance of intermolecular hydrogen bonds in the stabilization of the complexes. The method was applied to the fast quantification of the enantiomeric purity of in-process samples of S-omeprazole.

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Section: Introductionmentioning

confidence: 99%

Use of (S)‐BINOL as NMR chiral solvating agent for the enantiodiscrimination of omeprazole and its analogs

2009

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“…Owing to its high resolution, selectivity, and convenience, highperformance liquid chromatography (HPLC) is an important analytical tool in the study of food, herbal medicines, and other natural extracts. [16][17][18][19] Chemical fingerprints based on chromatographic profiles have been recommended as a method for assessing natural products. 20 Similarity evaluation or pattern recognition algorithms can be applied to such chromatographic fingerprints to identify the chemical richness or novelty of complex mixtures, and many studies on chromatographic fingerprint methods have now been reported.…”

Section: Introductionmentioning

confidence: 99%

Chromatographic Fingerprint-Bioactivity Relationships of the Antitumor Properties of Bufo bufo gargarizans Skin Extracts

et al. 2016

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Statistical analyses of high-performance liquid chromatography (HPLC)-based chemical fingerprints of Bufo bufo gargarizans toad skin extracts were integrated with antitumor evaluations as a means to more effectively identify bioactive constituents. Specifically, chemical fingerprints of Bufo bufo gargarizans skin extract samples obtained from ten different regions in China were generated by HPLC, and then subjected to similarity analysis and principal component analysis (PCA). Concurrently, a MCF-7 breast cancer cell model was adopted to obtain the antitumor activity of different toad skin extracts. The chromatographic fingerprint-bioactivity relationships of the Bufo bufo gargarizans extracts were then evaluated by Pearson correlation analysis. The results demonstrated that all skin extract samples inhibited the proliferation of MCF-7 cells to some extent, and that there was a correlation between the chemical fingerprints and the anti-proliferative activity. Bufotalin, bufalin, and cinobufagin, three known components of Bufo bufo gargarizans that were identified in the chemical fingerprints, were highlighted as constituents responsible for the observed bioactivity. The activity of cinobufagin was confirmed by cell viability and colony formation assays using MCF-7 cells. The approach documented here provides a more effective means to associate chemical information on medicinal extracts with the principle components responsible for their bioactivity, and to therefore expedite drug discovery.

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“…In continuation of previous studies on applicability of Chiralpak IA CSP in aqueous conditions [31], the influ- ence of addition of water to methanol and ethanol on enantioselectivity was investigated. The composition of aqueous eluents and the obtained RP chromatographic results are summarised in Fig.…”

Section: Resultsmentioning

confidence: 99%

Enantioseparation of kavain on Chiralpak IA under normal‐phase, polar organic and reversed‐phase conditions

Cirilli

Ferretti

Gallinella

et al. 2008

J of Separation Science

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First baseline HPLC enantioseparation of kavain is described. Complete enantiodiscrimination was achieved on the immobilised-type Chiralpak IA chiral stationary phase (CSP) using pure methanol and simple methanol-water and ethanol-water mixtures as eluents. A water-dependent enantioselectivity was clearly demonstrated. Performance of the Chiralpak IA CSP in polar organic and RP conditions was compared with that of five coated polysaccharide-derived CSPs used in normal-phase mode.

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High-performance liquid chromatography enantioseparation of proton pump inhibitors using the immobilized amylose-based Chiralpak IA chiral stationary phase in normal-phase, polar organic and reversed-phase conditions

Cited by 71 publications

References 32 publications

Use of (S)‐BINOL as NMR chiral solvating agent for the enantiodiscrimination of omeprazole and its analogs

Use of (S)‐BINOL as NMR chiral solvating agent for the enantiodiscrimination of omeprazole and its analogs

Chromatographic Fingerprint-Bioactivity Relationships of the Antitumor Properties of Bufo bufo gargarizans Skin Extracts

Enantioseparation of kavain on Chiralpak IA under normal‐phase, polar organic and reversed‐phase conditions

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