A metal organic framework-functionalized monolithic column for enantioseparation of six basic chiral drugs by capillary electrochromatography

Mikrochim Acta. 2019 Dec 17;187(1):51. doi: 10.1007/s00604-019-3998-0.

Abstract

Poly(glycidyl methacrylate)-co-(ethylene dimethacrylate) [poly(GMA-co-EDMA)] monoliths were used as a support to grow a zeolitic imidazolate framework-8 (ZIF-8) via layer-by-layer self-assembly. Pepsin, acting as as chiral selector, was covalently linked to the surface of the amino-modified ZIF-8 through the Schiff base method. The material was characterized by scanning electron microscopy, thermogravimetric analysis, X-ray diffraction, Fourier transform infrared spectroscopy and elemental analysis. The pepsin-ZIF-8-poly(GMA-co-EDMA) column was utilized to the enantioseparation of the racemic forms of hydroxychloroquine (HCQ), chloroquine (CHQ), hydroxyzine (HXY), nefopam (NEF), clenbuterol (CLE) and amlodipine (AML). In comparison with a pepsin-poly(GMA-co-EDMA) monolithic column (without self-assembled ZIF-8 nanoparticles), the resolution is strongly enhanced (HCQ: 0.34 → 2.50; CHQ: 0.45 → 1.97; HXY: 0.39 → 1.43; NEF: 0.27 → 0.81; CLE: 0 → 0.81; AML: 0.16 → 0.72). Effects of self-assembly layers of ZIF-8, pepsin concentration, buffer pH values and applied voltage were investigated with hydroxychloroquine as the model analyte. The reproducibility of run-to-run, day-to-day and column-to-column were explored, and found to be satisfactory. Graphical abstractSchematic representation of capillary electrochromatography (CEC) systems with a pepsin-zeolitic imidazolate framework-8 (ZIF-8) modified poly(glycidyl methacrylate)-co-(ethylene dimethacrylate) [poly(GMA-co-EDMA)] monolithic column as stationary phases for separation of basic racemic drugs. ZIF-8 modified column was prepared via layer-by-layer self-assembly.

Keywords: Basic drugs; Capillary electrochromatography; Enantioseparation; Glycidyl methacrylate; Metal-organic framework; Monolithic column; Nanoparticles; Pepsin; Self assembly; ZIF-8.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amlodipine / analysis
  • Capillary Electrochromatography
  • Chloroquine / analysis
  • Clenbuterol / analysis
  • Ethylene Glycols / chemistry*
  • Hydroxychloroquine / analysis
  • Hydroxyzine / analysis
  • Metal-Organic Frameworks / chemistry*
  • Methacrylates / chemistry*
  • Molecular Structure
  • Nefopam / analysis
  • Particle Size
  • Stereoisomerism
  • Surface Properties

Substances

  • Ethylene Glycols
  • Metal-Organic Frameworks
  • Methacrylates
  • poly(glycidyl methacrylate-co-ethylene glycol dimethacrylate)
  • Amlodipine
  • Hydroxyzine
  • Hydroxychloroquine
  • Nefopam
  • Chloroquine
  • Clenbuterol