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Analytical enantioseparation of N-alkyl drugs by reversed-phase liquid chromatography with carboxymethyl-β-cyclodextrin as mobile phase additive.
Chirality. 2023 01; 35(1):58-66.C

Abstract

Carboxymethyl-β-cyclodextrins (CM-β-CDs) with five kinds of degrees of substitution were synthesized and characterized. Analytical enantioseparation of six basic drugs containing N-alkyl groups, including pheniramine, chlorpheniramine, labetalol, propranolol, venlafaxine, and trans-paroxol, was achieved by reversed-phase high-performance liquid chromatography (RP-HPLC) using the synthesized CM-β-CD as chiral mobile phase additives. Key influence factors were optimized, including organic modifier, pH value, CM-β-CD with different degrees of substitution, and concentration of CM-β-CD. The mobile phase was composed of methanol and 10 mmol L-1 of phosphate buffer pH 4.0 containing 10 mmol L-1 of CM-β-CD. Peak resolution for six racemic drugs was gradually increased with an increasing degree of substitution of the synthesized CM-β-CD. The stoichiometric ratio and binding constants for the inclusion complex formed by CM-β-CD and enantiomer were determined, which showed that the stoichiometric ratio for each inclusion complex was 1:1.

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Publisher Full Text (DOI)

Authors+Show Affiliations

College of Pharmaceutical Science, Zhejiang University of Technology, Huzhou, China.

College of Pharmaceutical Science, Zhejiang University of Technology, Huzhou, China.

College of Pharmaceutical Science, Zhejiang University of Technology, Huzhou, China.

College of Pharmaceutical Science, Zhejiang University of Technology, Huzhou, China.

College of Pharmaceutical Science, Zhejiang University of Technology, Huzhou, China.

College of Pharmaceutical Science, Zhejiang University of Technology, Huzhou, China.

College of Pharmaceutical Science, Zhejiang University of Technology, Huzhou, China.

MeSH

Chromatography, Reverse-PhaseStereoisomerismChromatography, High Pressure Liquidbeta-CyclodextrinsIndicators and Reagents

Pub Type(s)

Journal Article

Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

36345792

Citation

You, Haibo, et al. "Analytical Enantioseparation of N-alkyl Drugs By Reversed-phase Liquid Chromatography With Carboxymethyl-β-cyclodextrin as Mobile Phase Additive." Chirality, vol. 35, no. 1, 2023, pp. 58-66.

You H, Chen B, Fang L, et al. Analytical enantioseparation of N-alkyl drugs by reversed-phase liquid chromatography with carboxymethyl-β-cyclodextrin as mobile phase additive. Chirality. 2023;35(1):58-66.

You, H., Chen, B., Fang, L., Lin, T., Xu, P., Chu, C., & Tong, S. (2023). Analytical enantioseparation of N-alkyl drugs by reversed-phase liquid chromatography with carboxymethyl-β-cyclodextrin as mobile phase additive. Chirality, 35(1), 58-66. https://doi.org/10.1002/chir.23516

You H, et al. Analytical Enantioseparation of N-alkyl Drugs By Reversed-phase Liquid Chromatography With Carboxymethyl-β-cyclodextrin as Mobile Phase Additive. Chirality. 2023;35(1):58-66. PubMed PMID: 36345792.

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

TY - JOUR T1 - Analytical enantioseparation of N-alkyl drugs by reversed-phase liquid chromatography with carboxymethyl-β-cyclodextrin as mobile phase additive. AU - You,Haibo, AU - Chen,Ben, AU - Fang,Liqun, AU - Lin,Tingting, AU - Xu,Ping, AU - Chu,Chu, AU - Tong,Shengqiang, Y1 - 2022/11/08/ PY - 2022/10/07/revised PY - 2022/06/28/received PY - 2022/10/26/accepted PY - 2022/11/9/pubmed PY - 2022/12/17/medline PY - 2022/11/8/entrez KW - N-alkyl drugs KW - carboxymethyl-β-cyclodextrin KW - chiral mobile phase additive KW - enantioseparation KW - reversed-phase liquid chromatography SP - 58 EP - 66 JF - Chirality JO - Chirality VL - 35 IS - 1 N2 - Carboxymethyl-β-cyclodextrins (CM-β-CDs) with five kinds of degrees of substitution were synthesized and characterized. Analytical enantioseparation of six basic drugs containing N-alkyl groups, including pheniramine, chlorpheniramine, labetalol, propranolol, venlafaxine, and trans-paroxol, was achieved by reversed-phase high-performance liquid chromatography (RP-HPLC) using the synthesized CM-β-CD as chiral mobile phase additives. Key influence factors were optimized, including organic modifier, pH value, CM-β-CD with different degrees of substitution, and concentration of CM-β-CD. The mobile phase was composed of methanol and 10 mmol L-1 of phosphate buffer pH 4.0 containing 10 mmol L-1 of CM-β-CD. Peak resolution for six racemic drugs was gradually increased with an increasing degree of substitution of the synthesized CM-β-CD. The stoichiometric ratio and binding constants for the inclusion complex formed by CM-β-CD and enantiomer were determined, which showed that the stoichiometric ratio for each inclusion complex was 1:1. SN - 1520-636X UR - https://www.unboundmedicine.com/medline/citation/36345792/Analytical_enantioseparation_of_N_alkyl_drugs_by_reversed_phase_liquid_chromatography_with_carboxymethyl_β_cyclodextrin_as_mobile_phase_additive_ DB - PRIME DP - Unbound Medicine ER -