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Enantioseparation of five racemic N-alkyl drugs by reverse phase HPLC using sulfobutylether-β-cyclodextrin as a chiral mobile phase additive.
J Sep Sci. 2022 Jun; 45(11):1847-1855.JS

Abstract

Analytical enantioseparations of five N-alkyl drugs, fluoxetine hydrochloride, labetalol, venlafaxine hydrochloride, trans-paroxol, and atropine sulfate, were investigated by reverse phase high-performance liquid chromatography with sulfobutylether-β-cyclodextrin as chiral mobile phase additive. Effects of various factors such as composition of mobile phase, concentration of cyclodextrins, and column temperature on retention and enantioselectivity were studied. Apparent formation constant between methanol, acetonitrile, and sulfobutylether-β-cyclodextrin were determined to be 2.90 × 10-3 and 1.00 × 10-4 L mmol-1 under 25°C using UV-spectrophotometry. Van't Hoff plots were used to investigate thermodynamic parameters for enantiomers-stationary phase interaction and formation of inclusion complex. Two retention models were employed individually for evaluation of inclusion complexation between five racemates and sulfobutylether-β-cyclodextrin. The second model with complex adsorption was more accord with the retention behavior of fluoxetine hydrochloride, labetalol, and venlafaxine hydrochloride enantiomers, while the first model was more consistent with the retention behaviors of trans-paroxol and atropine sulfate. In the selected mobile phase, stoichiometric ratio for both of inclusion complex was found to be 1:1.

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Publisher Full Text (DOI)

Authors+Show Affiliations

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, P. R. China.

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, P. R. China.

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, P. R. China.

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, P. R. China.

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, P. R. China.

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, P. R. China.

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, P. R. China.

MeSH

AtropineChromatography, High Pressure LiquidFluoxetineIndicators and ReagentsLabetalolStereoisomerismVenlafaxine Hydrochloridebeta-Cyclodextrins

Pub Type(s)

Journal Article

Language

eng

PubMed ID

35322921

Citation

Chen, Ben, et al. "Enantioseparation of Five Racemic N-alkyl Drugs By Reverse Phase HPLC Using Sulfobutylether-β-cyclodextrin as a Chiral Mobile Phase Additive." Journal of Separation Science, vol. 45, no. 11, 2022, pp. 1847-1855.

Chen B, You H, Fang L, et al. Enantioseparation of five racemic N-alkyl drugs by reverse phase HPLC using sulfobutylether-β-cyclodextrin as a chiral mobile phase additive. J Sep Sci. 2022;45(11):1847-1855.

Chen, B., You, H., Fang, L., Lin, T., Xu, P., Chu, C., & Tong, S. (2022). Enantioseparation of five racemic N-alkyl drugs by reverse phase HPLC using sulfobutylether-β-cyclodextrin as a chiral mobile phase additive. Journal of Separation Science, 45(11), 1847-1855. https://doi.org/10.1002/jssc.202200004

Chen B, et al. Enantioseparation of Five Racemic N-alkyl Drugs By Reverse Phase HPLC Using Sulfobutylether-β-cyclodextrin as a Chiral Mobile Phase Additive. J Sep Sci. 2022;45(11):1847-1855. PubMed PMID: 35322921.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Enantioseparation of five racemic N-alkyl drugs by reverse phase HPLC using sulfobutylether-β-cyclodextrin as a chiral mobile phase additive. AU - Chen,Ben, AU - You,Haibo, AU - Fang,Liqun, AU - Lin,Tingting, AU - Xu,Ping, AU - Chu,Chu, AU - Tong,Shengqiang, Y1 - 2022/04/04/ PY - 2022/02/24/revised PY - 2022/01/04/received PY - 2022/03/18/accepted PY - 2022/3/25/pubmed PY - 2022/6/11/medline PY - 2022/3/24/entrez KW - apparent formation constant KW - chiral separation KW - cyclodextrins KW - high-performance liquid chromatography SP - 1847 EP - 1855 JF - Journal of separation science JO - J Sep Sci VL - 45 IS - 11 N2 - Analytical enantioseparations of five N-alkyl drugs, fluoxetine hydrochloride, labetalol, venlafaxine hydrochloride, trans-paroxol, and atropine sulfate, were investigated by reverse phase high-performance liquid chromatography with sulfobutylether-β-cyclodextrin as chiral mobile phase additive. Effects of various factors such as composition of mobile phase, concentration of cyclodextrins, and column temperature on retention and enantioselectivity were studied. Apparent formation constant between methanol, acetonitrile, and sulfobutylether-β-cyclodextrin were determined to be 2.90 × 10-3 and 1.00 × 10-4 L mmol-1 under 25°C using UV-spectrophotometry. Van't Hoff plots were used to investigate thermodynamic parameters for enantiomers-stationary phase interaction and formation of inclusion complex. Two retention models were employed individually for evaluation of inclusion complexation between five racemates and sulfobutylether-β-cyclodextrin. The second model with complex adsorption was more accord with the retention behavior of fluoxetine hydrochloride, labetalol, and venlafaxine hydrochloride enantiomers, while the first model was more consistent with the retention behaviors of trans-paroxol and atropine sulfate. In the selected mobile phase, stoichiometric ratio for both of inclusion complex was found to be 1:1. SN - 1615-9314 UR - https://www.unboundmedicine.com/medline/citation/35322921/Enantioseparation_of_five_racemic_N_alkyl_drugs_by_reverse_phase_HPLC_using_sulfobutylether_β_cyclodextrin_as_a_chiral_mobile_phase_additive_ DB - PRIME DP - Unbound Medicine ER -