Chiral Method Development Strategies for HPLC using Macrocyclic Glycopeptide-Based Stationary Phases

Cardoso, Priscila Aburachid; César, Isabela Costa

doi:10.1007/s10337-018-3526-0

Cited by 33 publications

(24 citation statements)

References 32 publications

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“…The chemical structure of these stationary phases enables various interactions with separated analytes, such as hydrophobic, π-π, dipole-dipole, hydrogen, electrostatic, ionic, and van der Waals interactions [32], as well as complex formation [33]. In turn, chiral recognition is possible due to a large number of stereogenic centers [34,35]. Teicoplanin contains amide linkages and sugar residues.…”

Section: Scheme 1 Schematic Representations Of Stationary Phases (A)mentioning

confidence: 99%

Teicoplanin-Modified HPLC Column as a Source of Experimental Parameters for Prediction of the Anticonvulsant Activity of 1,2,4-Triazole-3-Thiones by the Regression Models

et al. 2020

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The cell membrane is a complex system that consists of lipids, proteins, polysaccharides, and amphiphilic phospholipids. It plays an important role in ADME processes that are responsible for the final pharmaceutical effects of xenobiotics (bioavailability, activity). To study drug-membrane interaction at the molecular level, several high-performance liquid chromatography (HPLC) membrane model systems have been proposed which are mimicking mainly its lipid character. The aim of this work was to study interactions of new synthesized antiepileptic compounds of 4-alkyl-5-(3-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione derivatives with Chirobiotic column containing glycoprotein ligand attached to the silica matrix. The affinity of the analytes to immobilized glycoprotein ligand was examined chromatographically in reversed-phase mode. The thermodynamics of interactions between bioactive compounds and teicoplanin was studied in terms of the van’t Hoff linear relationship ln k vs. 1/T in the range of 5–45 °C. Change in enthalpy (ΔH°), change in entropy (ΔS°) and change in Gibbs free energy (ΔG°) were estimated utilizing graphical extrapolation and interpolation methods. The density functional theory (DFT) approach and docking simulations were used to get the molecular interpretation and prove the obtained experimental results. Cross-correlations of chromatographic and thermodynamic parameters with non-empirical topological and quantum chemical indices suggest that the polarizability of analytes appears to be responsible for the interactions of the tested molecules with teicoplanin and, ultimately, their retention on the column. Experimental and theoretical parameters were subjected to statistical analysis using regression models. Partial least squares (PLS) regression model showed the usefulness of the experimentally measured parameter φ0 (MeOH) to discriminate between anticonvulsant active and inactive 1,2,4-triazole-3-thione derivatives. Obtained results point out the usefulness of interaction of potential anticonvulsants with glycoprotein class of compounds to anticipate their activity.

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Section: Scheme 1 Schematic Representations Of Stationary Phases (A)mentioning

confidence: 99%

Teicoplanin-Modified HPLC Column as a Source of Experimental Parameters for Prediction of the Anticonvulsant Activity of 1,2,4-Triazole-3-Thiones by the Regression Models

et al. 2020

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“…The physical chemistry of the stationary phases in liquid chromatography has been discussed to explain the use of ILs as silanol suppressors [69]. ILs have been immobilized for practical use as stationary phases in liquid chromatography [70][71][72][73][74][75][76]. A surface-initiated radical chain-transfer polymerization method was applied with 1-vinyl-3-octadecylimidazolium bromide as an IL monomer.…”

Section: Typical Structures Of Bonded-phase For Hilicmentioning

confidence: 99%

“…ILs have been immobilized as stationary phases for liquid chromatography [74]. The optimization of HPLC conditions and parameters for the chiral resolution of racemic drugs on macrocyclic glycopeptide-based chiral stationary phases was discussed [75]. The feasibility of immobilized IL phases has been described [76].…”

Section: Typical Structures Of Bonded-phase For Hilicmentioning

confidence: 99%

Fundamental Properties of Packing Materials for Liquid Chromatography

Hanai¹

2019

Separations

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The high performance of chemically-modified silica gel packing materials is based on the utilization of pure silica gels. Earlier silica gels used to be made from inorganic silica; however, nowadays, silica gels are made from organic silanes. The surface smoothness and lack of trace metals of new silica gels permits easy surface modifications (chemical reactions) and improves the reproducibility and stability. Sharpening peak symmetry is based on developing better surface modification methods (silylation). Typical examples can be found in the chromatography of amitriptyline for silanol testing and that of quinizarin for trace metal testing. These test compounds were selected and demonstrated sensitive results in the measurement of trace amounts of either silanol or trace metals. Here, we demonstrate the three-dimensional model chemical structures of bonded-phase silica gels with surface electron density for easy understanding of the molecular interaction sites with analytes. Furthermore, a quantitative explanation of hydrophilic and hydrophobic liquid chromatographies was provided. The synthesis methods of superficially porous silica gels and their modified products were introduced.

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“…Most quinoles are racemic and, hence, are separated because only one enantiomer is pharmaceutically active, while the other may be toxic, ballast, or inactive. [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] Therefore, to avoid the toxicities, side effects, and other problems, these quinolones should be administered in the form of pharmaceutically active pure enantiomers. The scientists, clinicians, industrialists, and government authorities are asking data on the chiral resolution of biologically important molecules including quinolones.…”

Section: Introductionmentioning

confidence: 99%

“…The most commonly used quinolones are primaquine, tafenoquine, flumequine, lomefloxacin, ofloxacin, and qunacrine (Figure ) because of their unique pharmaceutical properties. Most quinoles are racemic and, hence, are separated because only one enantiomer is pharmaceutically active, while the other may be toxic, ballast, or inactive . Therefore, to avoid the toxicities, side effects, and other problems, these quinolones should be administered in the form of pharmaceutically active pure enantiomers.…”

Section: Introductionmentioning

confidence: 99%

Chiral separation and modeling of quinolones on teicoplanin macrocyclic glycopeptide antibiotics CSP

Ali

Suhail

2018

Chirality

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New chiral high‐performance liquid chromatography (HPLC) method for the enantiomeric resolution of quinolones is developed and described. The column used was Chirobiotic T (150 × 4.6 mm, 5.0 μm). Three mobile phases used were MeOH:ACN:Water:TEA (70:10:20:0.1%), (60:30:10:0.1%), and (50:30:20:0.1%). The flow rate of the mobile phases was 1.0 mL/min with UV detection at different wavelengths. The values of retention, resolution, and separation factors ranged from 1.5 to 6.0, 1.80 to 2.25, and 2.86 to 6.0, respectively. The limit of detection and quantification ranged from 4.0 to 12 ng and 40 to 52 ng, respectively. The modeling studies indicated strong interactions of R‐enantiomers with teicoplanin chiral selector than S‐enantiomers. The supra molecular mechanism of the chiral recognition was established by modeling and chromatographic studies. It was observed that hydrogen bondings and π‐π interactions are the major forces for chiral separation. The present chiral HPLC method may be used for enantiomeric resolution of quinolones in any matrices.

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Chiral Method Development Strategies for HPLC using Macrocyclic Glycopeptide-Based Stationary Phases

Cited by 33 publications

References 32 publications

Teicoplanin-Modified HPLC Column as a Source of Experimental Parameters for Prediction of the Anticonvulsant Activity of 1,2,4-Triazole-3-Thiones by the Regression Models

Teicoplanin-Modified HPLC Column as a Source of Experimental Parameters for Prediction of the Anticonvulsant Activity of 1,2,4-Triazole-3-Thiones by the Regression Models

Fundamental Properties of Packing Materials for Liquid Chromatography

Chiral separation and modeling of quinolones on teicoplanin macrocyclic glycopeptide antibiotics CSP

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