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Theoretical design and selectivity researches on the enrofloxacin imprinted polymer

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Abstract

In this paper, enrofloxacin (ENRO) was chosen as the template molecule, 4-vinylpyridine (4-Vpy), acrylamide (AM), trifluoromethacrylic acid (TFMAA), and 2-hydroxyethyl methacrylate (HEMA) were selected as the functional monomers, with the following cross-linking agents, ethylene glycol dimethacrylate (EDMA), pentaerythritol triacrylate (PETA), and trimethylolpropane trimethacrylate (TRIM). The stable complex configurations formed by ENRO and four monomers at the molar ratio of 1:1 were calculated using the density functional theory at the B3LYP/6-31G(d,p) level. Their natural bond orbital charges and the action sites were discussed to screen the appropriate functional monomer. The optimal molar ratio of template–monomer complex and the effects of cross-linking agent were investigated. The nature of the imprinting interaction was also researched via the infrared spectrum. The results reveal that the complex formed from ENRO and TFMAA has the strongest hydrogen bond interaction. When the molar ratio is 1:7, the complex has the most stable configuration. Owning to the weakest interaction between EDMA and ENRO, and the strongest interaction between EDMA and TFMAA, EDMA is considered as the suitable cross-linking agent, in comparison with PETA and TRIM for ENRO-MIPs. After the removal of ENRO molecule, the most stable ENRO-TFMAA complex owing to the better binding capacity to ENRO is compared with its structural analogues (ciprofloxacin, sparfloxacin, pefloxacin, ofloxacin, and sarafloxacin). This study provides a reliable theoretical guidance for the preparation of new ENRO-MIPs.

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Acknowledgments

The financial supports from the National Natural Science Foundation of China (Nos. 21302062, 21301048, and 21563002) and the Science and Technology Development Plan of Jilin Province (Nos. 20130206099SF and 20150101018JC) are gratefully acknowledged.

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Authors and Affiliations

  1. College of Resources and Environment, Jilin Agricultural University, Changchun, 130118, China

    Zheng-qiang Dai, Jun-bo Liu, Shan-shan Tang & Yan Wang

  2. Hebei Provincial Key Laboratory of Inorganic Nonmetallic Materials, College of Materials Science and Engineering, North China University of Science and Technology, Tangshan, 063009, China

    Bo Li

  3. College of Chemistry and Chemical Engineering, Chifeng University, Chifeng, 024000, China

    Rui-fa Jin

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  1. Zheng-qiang Dai
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  2. Jun-bo Liu
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  3. Shan-shan Tang
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  4. Yan Wang
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  5. Bo Li
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Correspondence to Jun-bo Liu or Shan-shan Tang.

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Dai, Zq., Liu, Jb., Tang, Ss. et al. Theoretical design and selectivity researches on the enrofloxacin imprinted polymer. Struct Chem 27, 1135–1142 (2016). https://doi.org/10.1007/s11224-015-0735-0

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  • DOI: https://doi.org/10.1007/s11224-015-0735-0

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