Stereoselective separation of isomeric sertraline with analytical countercurrent chromatography.
Sertraline is an antidepressant in a group of drugs called selective serotonin reuptake inhibitors. Four stereoisomeric compounds would be produced in its synthetic preparation due to two chiral carbons on its chemical structures. In the present work, stereoselective liquid-liquid extraction of isomeric sertraline with substituted cyclodextrins as stereoselective extractant was investigated. Factors affecting the distribution performance, including organic solvents, types of extractants, pH value, buffer solution of aqueous phase, concentration of extractant and temperature, were investigated. Under optimized conditions, a stereoselectivity of 1.404 was obtained for cis-sertraline and a stereoselectivity of 2.373 was obtained for trans-sertraline when hydroxypropyl-β-cyclodextrin was used as the stereoselective extractant, and a stereoselectivity of 1.685 was achieved for trans-sertraline with methyl-β-cyclodextrin as extractant. An unusual stereoselective combination was observed for trans-sertraline and cis-sertraline when sodium carbonate buffer was used. Successful stereoselective separation of trans-sertraline and cis-sertraline, (1S, 4R) and (1R, 4S)-sertraline by analytical countercurrent chromatography with methyl-β-cyclodextrin as stereoselective selector was achieved, using a biphasic solvent system composed of n-hexane : 0.1 mol L-1 citrate buffer solution with pH7.6 (1:1, v/v).
['Sun|Wenyu|W|', 'Jin|Yang|Y|', 'Wang|Chaoyue|C|', 'Zhao|Shanshan|S|', 'Wang|Xiang|X|', 'Luo|Meng|M|', 'Yan|Jizhong|J|', 'Tong|Shengqiang|S|']
D000073738:2-Hydroxypropyl-beta-cyclodextrin D000928:Antidepressive Agents D003377:Countercurrent Distribution D003505:Cyclodextrins D059625:Liquid-Liquid Extraction D017367:Serotonin Uptake Inhibitors D020280:Sertraline D012997:Solvents D013237:Stereoisomerism D047392:beta-Cyclodextrins
Isomeric sertraline Countercurrent chromatography Stereoselective liquid-liquid extraction Hydroxypropyl-β-cyclodextrin Methyl-β-cyclodextrin