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Gold nanoparticles-functionalized monolithic column for enantioseparation of eight basic chiral drugs by capillary electrochromatography

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Abstract

Poly(glycidyl methacrylate)-co-(ethylene dimethacrylate) [poly(GMA-co-EDMA)] monoliths were prepared, and used as a support to attach gold nanoparticles (AuNP) via Au-S bond. Pepsin, acting as a chiral selector, was linked to the surface of the carboxyl-modified AuNP through a hydrochloride/N-hydroxysuccinimide coupling reaction. The material was characterized by scanning electron microscopy, energy dispersive X-ray spectrometry, transmission electron microscopy, thermogravimetric analysis, Fourier transform infrared spectroscopy and N2 adsorption-desorption isotherm. The pepsin@AuNP@poly(GMA-co-EDMA) monolith showed preferable enantioselectivity for hydroxychloroquine (HCQ), chloroquine (CHQ), hydroxyzine (HXY), labetalol (LAB), nefopam (NEF), clenbuterol (CLE), amlodipine (AML) and chlorpheniramine (CHL) in capillary electrochromatography (CEC). These racemic drugs were monitored at the maximum absorption wavelength (220 nm for HXQ, CHQ, HXY, LAB, NEF; 240 nm for AML; 215 nm for CLE, CHL). In comparison with the pepsin@poly(GMA-co-EDMA) monolith loaded with 5 nm AuNP, the pepsin@poly(GMA-co-EDMA) monolith loaded with 13 nm AuNP shows significantly enhanced enantiomeric resolution (HCQ: 0.62 → 3.45; CHQ: 0.60 → 2.11; HXY: 0.49 → 2.30; LAB: 1.03 → 2.45, 1.45 → 3.46, 0 → 0.67; NEF: 0.53 → 1.29; CLE: 0.42 → 0.56; AML: 0 → 0.83; CHL: 0.24 → 0.55). Pepsin concentration, buffer pH value, buffer concentration and applied voltage were investigated in detail with (±) HCQ and (±) HXY as model analytes. The reproducibility of intra-day, inter-day and column-to-column were explored, and found to be satisfactory.

Schematic presentation of the preparation of gold nanoparticles (AuNP) modified.

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Acknowledgements

This work was supported by the Natural Science Foundation of Jiangsu Province (Program No.: BK20141353).

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Authors and Affiliations

  1. Key Laboratory of Drug Quality Control and Pharmacovigilance (Ministry of Education), China Pharmaceutical University, No.24 Tongjiaxiang, Nanjing, Jiangsu, 210009, People’s Republic of China

    Mingxuan Ma, Yingxiang Du, Jiangxia Yang, Zijie Feng, Wen Ding & Cheng Chen

  2. State Key Laboratory of Natural Medicines, China Pharmaceutical University, No.24 Tongjiaxiang, Nanjing, Jiangsu, 210009, People’s Republic of China

    Mingxuan Ma, Yingxiang Du, Jiangxia Yang, Zijie Feng, Wen Ding & Cheng Chen

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  1. Mingxuan Ma
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Correspondence to Yingxiang Du.

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Ma, M., Du, Y., Yang, J. et al. Gold nanoparticles-functionalized monolithic column for enantioseparation of eight basic chiral drugs by capillary electrochromatography. Microchim Acta 187, 178 (2020). https://doi.org/10.1007/s00604-020-4144-8

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