A molecularly imprinted monolith for the fast chiral separation of antiparasitic drugs by pressurized CEC

Abstract

Molecularly imprinted polymer (MIP) monoliths with (S)-ornidazole ((S)-ONZ) as the template molecule have been designed and prepared by the simple thermal polymerization of methacrylic acid, 4-vinylpyridine, and ethylene dimethacrylate in the presence of a binary porogenic mixture of toluene and dodecanol. The influences of polymerization mixture composition on the chiral recognition of ONZ have been evaluated, and the imprint effect in the optimized MIP monolith has been clearly demonstrated. The new monolithic stationary phase with optimized porous property and good selectivity was used for the chiral separation of ONZ by pressurized CEC. The pressurized CEC conditions were also optimized to obtain the good chiral separation. The enantiomers were rapidly separated within 9 min on the MIP-based chiral stationary phase, whereas the chiral separation was not obtained on the nonimprinted polymer. Additionally, the proposed method has been successfully applied to the chiral separation of ONZ in tablet samples by injection of the crude sample. The cross-selectivity for similar antiparasitic drug was investigated. The results indicated that the chiral separation of secnidazole could also be obtained on the optimized MIP monolith within 14 min.

Synthesis of a nano‐sized chiral imprinted polymer and its use as an (S)‐atenolol carrier in the bulk liquid membrane

“…In the first method, chiral template (L or D isomer) is utilized in the polymerization stage [9,11] and in the second way chiral template is replaced with chiral functional monomers [1,32]. In this work, we utilized the first synthesis strategy.…”

Recent developments and applications of molecularly imprinted monolithic column for HPLC and CEC

“…Recently, Li et al 116 reported the preparation of MIP monolith using the L ‐enantiomer of amino acid as the template molecule and investigated the chiral recognition of MIP monolith in pCEC. MIP monoliths with ( S )‐ornidazole (( S )‐ONZ) as the template molecule have been designed and prepared by the simple thermal polymerization of MAA, 4‐VP and EDMA in the presence of a binary porogenic mixture of toluene and dodecanol 117. The enantiomers were rapidly separated within 9 min on the MIP‐based chiral stationary phase by pCEC (Fig.…”

“…Due to high selectivity of MIP and high performance of CEC, MIP capillary monolith is usually used as the chiral stationary phase in the CEC mode, especially for separation of chiral drugs 108, 111–114, 116, 117, 123, 125–130. Simultaneously, MIP could also be used for the separation of positional isomers or structural analogues, which can be used to remove small amounts of impurities or isolate one of the expensive isomers or analogues 131–135.…”

Enantioselective HPLC determination and pharmacokinetic study of secnidazole enantiomers in rats

“…Liao et al [19] designed and prepared several molecularimprinted polymer monoliths with S-(−)-ornidazole as a template molecule for the rapid chiral separation of ornidazole enantiomers by pressurized capillary electrochromatography. They found that the chiral separation of secnidazole enantiomers was also achieved within 14 min using an optimized monolith.…”