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Citation: ZHENG Zhen, CHEN Xiujuan, ZHAO Liang, LI Wuhong, HONG Zhanying, CHAI Yifeng. Enantioseparation of milnacipran enantiomers and the separation mechanism on β-cyclodextrin-based chiral stationary phases by high performance liquid chromatography[J]. Chinese Journal of Chromatography, ;2017, 35(3): 286-290. doi: 10.3724/SP.J.1123.2016.09048 shu

Enantioseparation of milnacipran enantiomers and the separation mechanism on β-cyclodextrin-based chiral stationary phases by high performance liquid chromatography

ZHENG Zhen ^1,2, ,
CHEN Xiujuan ^1,3 ,
ZHAO Liang ⁴ ,
LI Wuhong ¹ ,
HONG Zhanying ¹ ,
CHAI Yifeng ¹

1.
School of Pharmacy, Second Military Medical University, Shanghai 200433, China;
2.
Medical Corps, 91837 Unit, People's Liberation Army of China, Zhoushan 316291, China;
3.
Fujian University of Traditional Chinese Medicine, Fuzhou 350108, China;
4.
Department of Pharmacy, Eastern Hepatobiliary Surgery Hospital, Second Military Medical University, Shanghai 200438, China

Received Date: 30 September 2016

Fund Project: National Natural Science Foundation of China (Nos. 81202497, 81373376).

A high performance liquid chromatography method was established for the enantiomeric separation of milnacipran enantiomers on β-cyclodextrin-based chiral stationary phases (CSPs). Chiral columns of Astec CYCLOBOND^TM I 2000 series, such as the native β-cyclodextrin (Cyclobond I 2000), acetyl-β-cyclodextrin (AC-β-CD), 2,3-dimethyl-β-cyclodextrin (DM-β-CD) and 3,5-dimethylphenyl carbamate β-cyclodextrin (DMP-β-CD), were examined under the reversed-phase mode. The effects of cyclodextrin stationary phase, mobile phase composition, pH, flow rate and column temperature on the separation of milnacipran enantiomers were investigated. The inclusion process between AC-β-CD and milnacipran enantiomers was investigated and chiral recognition mechanism was studied with molecular docking technique and binding energy calculations. The optimized conditions were as follows: the chiral stationary phase was a column of Astec CYCLOBOND^TM I 2000 AC (25 cm×4.6 mm, 5 μm), the mobile phase was acetonitrile-0.1% (v/v) pH 5.0 triethylamine acetate (TEAA) (5:95, v/v) with a flow rate of 0.4 mL/min and the detection wavelength was 220 nm. The injection volume was 10 μL and the column temperature was 25℃. The value of resolution (R_s) was 1.74 and the theoretical plates were 10125. The results suggested that hydrogen bonding ability played an important role in the chiral recognition process of milnacipran enantiomers. The developed method was rapid, effective and reproducible.
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