Mechanism of separation on cholesterol–silica stationary phase for high-performance liquid chromatography as revealed by analysis of quantitative structure–retention relationships

Al-Haj, Mehdi Ahmed; Haber, Piotr; Kaliszan, Roman; Buszewski, Bogusław; Jezierska, Marta; Chilmonzyk, Zdzisław

doi:10.1016/s0731-7085(98)00287-8

Cited by 58 publications

(29 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Nowadays, cholesterol columns are becoming more and more popular. [36][37][38][39] In the presented work, by comparing conventional octadecyl bonded phase with cholesterol column, confirms the suitability of cholesterol stationary phase for chromatographic analysis of urea derivatives and determination of their lipophilicity. It should be emphasized that to achieve better efficiency of chromatographic system containing cholesterol stationary phase, acetonitrile can be recommended in analysis of urea derivatives.…”

Section: Discussionsupporting

confidence: 70%

“…Nowadays, stationary phases with immobilized cholesterol, which is an important component of biological membranes are increasingly popular. 23,24 Cholesterol column possesses many advantageous properties like, for instance, low silanol activity or liquidcrystalline behavior owing to their tendency to aggregate. …”

mentioning

confidence: 99%

“…The synthesis procedure was described previously. 23 The structures of all the investigated solutes were confirmed by gas chromatography-mass spectrometry (GC-MS) analysis, 1 H nuclear magnetic resonance (NMR), 13 C NMR and infrared (IR) analysis and their purity was assessed by elemental analysis. HPLC grade methanol (MeOH), acetonitrile (ACN) and chromatographic reagents were obtained from E. Merck (Darmstadt, Germany).…”

mentioning

confidence: 99%

See 2 more Smart Citations

Fragmental Method KowWIN as the Powerful Tool for Prediction of Chromatographic Behavior of Novel Bioactive Urea Derivatives

Flieger¹,

Tatarczak-Michalewska²,

Kowalska³

et al. 2016

Journal of the Brazilian Chemical Society

View full text Add to dashboard Cite

A series of the new urea derivatives with antinociceptive activity has been chromatographically evaluated using reversed phase materials: Zorbax Extend-C18, Cogent UDC Cholesterol with organic-aqueous eluent systems with two organic modifiers (methanol and acetonitrile). The chromatographic lipophilicity parameters: log k w , S and j 0 were determined basing on linear relationship between log k values and concentration of organic mobile phase modifier. The structure-retention studies revealed that the retention mechanism for all studied urea derivatives is uniform for the proposed chromatographic systems. However, a few exceptions were noticed. Derivatives containing nonpolar substituents in the imidazole ring acted as outliers for cholesterol column. In turn, the derivative containing ester polar substituent acted as an outlier in conventional reversed-phase system. Quantitative relationships based on a wide set of established computational molecular descriptors and experimental chromatographic data were also developed. Through a systematic study, by using the principal component analysis, fragmental method KowWIN appeared to be the most powerful software to produce reliable estimations of experimental retention parameters obtained on cholesterol column.

show abstract

Section: Discussionsupporting

confidence: 70%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Fragmental Method KowWIN as the Powerful Tool for Prediction of Chromatographic Behavior of Novel Bioactive Urea Derivatives

Flieger¹,

Tatarczak-Michalewska²,

Kowalska³

et al. 2016

Journal of the Brazilian Chemical Society

View full text Add to dashboard Cite

show abstract

“…Liquid crystalline (LC) stationary phases (SPs) are widely used as a separation material in GC and have been around for over 40 years [1]. In addition, LC-SP has shown applications in supercritical fluid chromatography [2,3] and HPLC [4][5][6][7][8][9][10]. However, in comparison to GC, the use of LC-SPs in HPLC and supercritical fluid chromatography is less prevalent.…”

Section: Introductionmentioning

confidence: 99%

Packed‐column capillary electrochromatography and capillary electrochromatography‐mass spectrometry using a lithocholic acid stationary phase

Norton

Shamsi

2008

Electrophoresis

View full text Add to dashboard Cite

The preparation and characterization of a novel lithocholic acid (LCA)-based liquid crystalline (LC) stationary phase (SP) suitable for application in packed-column CEC and CEC coupled to MS is described. The extent of bonding reactions of LCA-SP was assessed using 1 H-NMR, 13 C-NMR and elemental analysis. This characterization is followed by application of the LCA-SP for separation of β-blockers, phenylethylamines (PEAs), polyaromatic hydrocarbons (PAHs) and polychlorinated biphenyls (PCBs). Using the optimum mobile phase operating conditions (pH 3.0-4.5, 10 mM ammonium acetate, 85% v/v ACN), a comparison of the chromatographic ability of the aminopropyl silica phase vs. the LCA-bonded phase was conducted. The results showed improved selectivity for all test analytes using the latter phase. For example, the CEC-MS of β-blockers demonstrated that the LCA-bonded phase provides separation of six out of seven β-blockers, whereas the amino silica phase provides four peaks of several co-eluting β-blockers. For the CEC-MS analysis of PEAs, the LCA-bonded phase showed improved resolution and different selectivity as compared to the aminopropyl phase. An evaluation of the retention trends for PEAs on both phases suggested that the PEAs were retained based on varying degree of hydroxyl substitution on the aromatic ring. In addition, the MS characterization shows several PEAs fragment in the electrospray either by loss of an alkyl group and/or by loss of H 2 O. Finally, the LCA-bonded phase displayed significantly higher separation selectivity for PAHs and PCBs as compared to the amino silica phase.

show abstract

“…27 Aside from their practical application in optimization strategies, QSRR studies can significantly contribute to clarify the molecular-based mechanism of chromatographic retention. [28][29][30] Multiple linear regression (MLR) is the method most frequently used for the statistical treatment of QSRR multivariate data consisting of a set of observed retention values and descriptors for a given set of test molecules. 31 In recent years, artificial neural networks (ANNs) 32,33 have gained popularity as a powerful chemometric tool that can be used for the treatment of multivariate chemical problems, such as the optimization of chromatographic analysis.…”

mentioning

confidence: 99%

Retention Prediction Modeling of Ginsenosides on a Polyvinyl Alcohol-bonded Stationary Phase at Subambient Temperatures Using Multiple Linear Regression and Artificial Neural Network

et al. 2008

View full text Add to dashboard Cite

Mechanism of separation on cholesterol–silica stationary phase for high-performance liquid chromatography as revealed by analysis of quantitative structure–retention relationships

Cited by 58 publications

References 28 publications

Fragmental Method KowWIN as the Powerful Tool for Prediction of Chromatographic Behavior of Novel Bioactive Urea Derivatives

Fragmental Method KowWIN as the Powerful Tool for Prediction of Chromatographic Behavior of Novel Bioactive Urea Derivatives

Packed‐column capillary electrochromatography and capillary electrochromatography‐mass spectrometry using a lithocholic acid stationary phase

Retention Prediction Modeling of Ginsenosides on a Polyvinyl Alcohol-bonded Stationary Phase at Subambient Temperatures Using Multiple Linear Regression and Artificial Neural Network

Contact Info

Product

Resources

About