scholarly journals Direct Enantiomeric Resolution of Seventeen Racemic 1,4-Dihydropyridine-Based Hexahydroquinoline Derivatives by HPLC

2019 ◽  
Vol 20 (10) ◽  
pp. 2513 ◽  
Author(s):  
Jiayi Sun ◽  
Miyase Gözde Gündüz ◽  
Junyuan Zhang ◽  
Jia Yu ◽  
Xingjie Guo
Keyword(s):  
Stationary Phase ◽  
High Performance ◽  
Chiral Stationary Phase ◽  
Reversed Phase ◽  
Chiral Separations ◽  
Racemic Mixture ◽  
Enantiomeric Resolution ◽  
Column Temperature ◽  
Limit Of Quantitation ◽  
Pharmacologically Active

1,4-Dihydropyridine (DHP) scaffold holds an outstanding position with its versatile pharmacological properties among all heterocyclic compounds. Although most of the commercially available DHPs are marketed as a racemic mixture, the chiral center at C-4 can lead to even opposite pharmacological activities between the enantiomers. In the present study, enantioseparation of seventeen DHP structural analogues, consisting of either pharmacologically active or newly synthesized derivatives, (M2-4, MD5, HM2, HM10, CE5, N11, N10, N7, M11, MC6-8, MC13, MD23, and 42IIP) by high-performance liquid chromatography was investigated using immobilized polysaccharide-based chiral stationary phase, Chiralpak IC column. Due to the solvent versatility of the covalently immobilized chiral stationary phase in enantiomer separation, multiple elution modes including standard normal phase, nonstandard mobile phase, and reversed phase were used to expand the possibility to find the optimum enantioselective conditions for the tested analytes. Under appropriate separation conditions, complete enantiomeric separation was obtained for nearly all compounds except MC6-8 and MC13 which contained two chiral centers. Additionally, the effects of the polar modifier, the additive, and column temperature on the chiral recognition were evaluated. The thermodynamic parameters calculated according to the linear van’t Hoff equation indicated that the chiral separations in this study were enthalpy-driven or entropy-driven. Some parameters of method validation such as linearity, limit of quantitation, and repeatability were also measured for all studied compounds to prove the reliability of the method.

A New Kind of Material for HPLC – Dioscin-Bonded Silica Gel Stationary Phase

2015 ◽  
Vol 723 ◽  
pp. 680-683
Author(s):  
Xin Yi Li ◽  
Xiao Juan Gu ◽  
Bao Chun Shen
Keyword(s):  
Stationary Phase ◽  
Silica Gel ◽  
High Performance ◽  
Panax Notoginseng ◽  
Active Pharmaceutical Ingredient ◽  
Reversed Phase ◽  
One Pot ◽  
Column Temperature ◽  
Hplc Fingerprint ◽  
New Stationary Phase

A new dioscin-bonded silica gel stationary phase with natural active ingredient for high performance liquid chromatography was prepared by one-pot reaction method, using 1,6-diisocyanate as the spacer arm. The structure of new stationary phase was characterized by solid-state NMR techniques, infrared spectroscopy, elemental analysis, thermogravimetric analysis and scanning electron microscope. These results show that the dioscin has been bonded to the silicia gel. The resulting stationary phase containes 127.6 μmol/g dioscin ligand. The chromatographic performance of this new stationary phase was evaluated by different kinds of solute probes. The results illustrate that the new stationary phase has a typical reversed phase chromatographic property, meanwhile it could present various interactions with solutes. The HPLC fingerprint of PNS(Panax Notoginseng saponins) API(active pharmaceutical ingredient) on the dioscin-bonded silica gel stationary phase was established. The mobile phase was consisted of gradient acetonitrile and water. The detection wavelength was 203 nm, the column temperature was maintained at 35 degrees Celsius, the flow rate was 0.8ml/min and the injection volumn was 15 μL. The contents of the 5 co-possessing components were determined simultaneously. A new material for HPLC was made by natural product. The using of dioscin-bonded silica gel stationary phase provides a new idea in natural products research.

scholarly journals Liquid chromatographic enantioseparation of thalidomide and its derivatives on cyclodextrin-bonded stationary phases

2018 ◽  
Vol 91 (2) ◽  
pp. 99-106
Author(s):  
Szabó-Zoltán István ◽  
Foroughbakhshfasaei Mohammadhassan ◽  
Dobó Máté ◽  
Noszál Béla ◽  
Tóth Gergő
Keyword(s):  
Acetic Acid ◽  
Stationary Phase ◽  
Flow Rate ◽  
Chiral Separation ◽  
Stationary Phases ◽  
Reversed Phase ◽  
Chiral Separations ◽  
Column Temperature ◽  
Bonded Stationary Phases ◽  
Chiral Interactions

Abstract The chiral separation of three racemic immunomodulatory drugs, thalidomide, pomalidomide and lenalidomide was studied, using three cyclodextrin bonded stationary phases (β-, hydroxypropyl-β- and carboxymethyl-β-CD) in reversed-phase and polar organic mode. In polar organic mode, using acetonitrile and methanol, no chiral separation was observed. In reversed-phase mode pomalidomide showed chiral interactions with all selectors, while lenalidomide showed no chiral interactions with any of the cyclodextrins employed. Thalidomide showed chiral interactions with β-and carboxymethyl-β-CD, only. Based on these observations it can be concluded that the oxo group at position two is necessary for chiral recognition, while the aromatic primary amine group enhances it. Orthogonal experimental design was used to investigate the effect of the eluent composition, flow rate, and the column temperature on chiral separation. Concentration of the organic modifier was the most important factor among the investigated three variables showing high impact on the chiral separations. In the case of thalidomide optimized parameters (β-cyclodextrin-based stationary phase, 0.1% acetic acid/acetonitrile 95/5 (v/v), 5 °C column temperature, 0.6 ml/min flow rate) resulted in a resolution of 1.68 ± 0.02 between enantiomers. For pomalidomide, this value was 2.70 ± 0.02, under the circumstances as follows: β-cyclodextrin-based stationary phase, 0.1% acetic acid/acetonitrile 90/10 (v/v), 15 °C column temperature and 0.8 mL/min flow rate. Utilizing the experimental conditions employed on an LC-MS/MS system, concentrations as low as 2 ng/mL could be determined from mouse plasma for both substances. Elution sequences were determined with enantiopure standards and in both cases the R-enantiomers eluted first. The methods developed are suitable for the chiral separation of the abovementioned compounds and are sound starting points for bioanalytical method development.

A cationic cyclodextrin clicked bilayer chiral stationary phase for versatile chiral separation in HPLC

2018 ◽  
Vol 42 (5) ◽  
pp. 3526-3533 ◽  
Author(s):  
Jie Zhou ◽  
Bo Yang ◽  
Jian Tang ◽  
Weihua Tang
Keyword(s):  
Stationary Phase ◽  
Click Chemistry ◽  
Chiral Separation ◽  
High Performance ◽  
Chiral Stationary Phase ◽  
Chiral Separations

A cationic cyclodextrin (CD) clicked bilayer chiral stationary phase (CSP) was developed via click chemistry for chiral separations in multimode high-performance chromatography (HPLC).

Chiral Separation of Racemic Naproxen by High-Performance Liquid Chromatography with β-CD/SiO2 as the Chiral Stationary Phase

2014 ◽  
Vol 97 (1) ◽  
pp. 121-127 ◽  
Author(s):  
Lili Wang ◽  
Jian Deng ◽  
Xuezhen Ji ◽  
Wanbin Liu ◽  
Jun Liang ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Separation ◽  
Photoelectron Spectroscopy ◽  
High Performance ◽  
Chiral Stationary Phase ◽  
Separation Efficiency ◽  
Phosphate Buffer Solution ◽  
Buffer Solution ◽  
Scanning Calorimetry ◽  
Column Temperature

Abstract A novel derivative β-cyclodextrin (β-CD) bonded silica gel (β-CD/SiO2) was prepared via carbodiimide activation and used as a chiral stationary phase (CSP). The β-CD/SiO2 CSP was characterizedby X-ray photoelectron spectroscopy and FTIR spectroscopy to prove the successful immobilization of β-CD onto the surface of the silica gel.The thermal behavior of the CSP was studied by differential scanning calorimetry and then used forthe chiral separation of racemic naproxen using HPLC. Several factors affecting the separation efficiency of naproxen enantiomers were investigatedsystematically. The following parameters were selected: methanol–0.01 M phosphate buffer solution (85 + 15, v/v, pH 3.5) was the mobile phase, the flow rate was 1.0 mL/min, and the column temperature was 35°C. Under optimal conditions, the racemic naproxen was efficiently separated with a resolution factor (RS) of 1.70 and a separation factor (α) of 1.25. This method was successfully used for the enantiomeric separation and purity assessment of naproxen in commercial naproxen sustained release tablets.

Sign in / Sign up

Export Citation Format

Share Document