Skip to main content
Log in

Properties evaluation and separation application of naringin-imprinted polymers prepared by a covalent imprinting method based on boronate ester

  • Original Paper
  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

Abstract

Covalent molecularly imprinted polymer (CMIP) for naringin was prepared with a conventional radical bulk polymerization by utilizing 4-vinylphenylboronic acid as a functional monomer and ethylene glycol dimethacrylate (EDMA) as a cross-linking agent. Properties such as adsorption dynamics, special binding, and selective recognition ability were evaluated. The results revealed that the CMIP possessed specific recognition ability and high molecular selectivity in contrast with a non-imprinted polymer in methanol-phosphate buffer (pH 8.0) (7/3, v/v), and the maximum equilibrium adsorption amount of CMIP reached 64.80 μmol.g−1. The adsorption equilibrium could be achieved within 3 h, which indicated that the adsorption dynamic was relatively fast. The CMIP was further employed as a sorbent of solid phase extraction (SPE) to directly separate naringin from Exocarpium citri grandi extract. The results showed that the CMIP could separate and enrich naringin from E. citri grandi extract effectively, and the special binding was calculated to be about 72 % of the total adsorption on the SPE cartridges.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Beltran A, Marce RM, Cormack PAG, Borrull F (2010) Synthetic approaches to parabens molecularly imprinted polymers and their applications to the solid-phase extraction of river water samples. Anal Chim Acta 677:72–78

    Article  CAS  Google Scholar 

  2. Shen ZL, Yuan D, Su QD, Zhang H, Wang J, Zhu JH, Liu YM (2011) Selective solid-phase extraction using molecularly imprinted polymer for analysis of methamidophos in water and soil samples. Biosci Biotechnol Biochem 75:473–479

    Article  CAS  Google Scholar 

  3. Baggiani C, Baravalle P, Giraudi G, Tozzi C (2007) Molecularly imprinted solid-phase extraction method for the high-performance liquid chromatographic analysis of fungicide pyrimethanil in wine. J Chromatogr A 1141:158–164

    Article  CAS  Google Scholar 

  4. Advincula RC (2011) Engineering molecularly imprinted polymer (MIP) materials: developments and challenges for sensing and separation technologies. Korean J Chem Eng 28:1313–1321

    Article  CAS  Google Scholar 

  5. Barde LN, Ghule MM, Roy AA, Mathur VB, Shivhare UD (2013) Development of molecularly imprinted polymer as sustain release drug carrier for propranolol HCL. Drug Dev Ind Pharm 39:1247–1253

    Article  CAS  Google Scholar 

  6. He JF, Zhu QH, Deng QY (2007) Investigation of imprinting parameters and their recognition nature for quinine-molecularly imprinted polymers. Spectrochim Acta A 67:1297–1305

    Article  Google Scholar 

  7. Mayes AG, Whitcombe MJ (2005) Synthetic strategies for the generation of molecularly imprinted organic polymers. Adv Drug Deliv Rev 57:1742–1778

    Article  CAS  Google Scholar 

  8. Jagetia GC, Reddy TK (2005) Modulation of radiation-induced alteration in the antioxidant status of mice by naringin. Life Sci 77:780–794

    Article  CAS  Google Scholar 

  9. Zhai YK, Niu YB, Pan YL, Li CR, Wu XL, Mei QB (2013) Effects of naringin on proliferation, differentiation and maturation of rat calvarial osteoblasts in vitro. China J Chin Mater Med 38:105–111 (in China)

    Article  CAS  Google Scholar 

  10. Okutucu B, Önal S (2011) Molecularly imprinted polymers for separation of various sugars from human urine. Talanta 87:74–79

    Article  CAS  Google Scholar 

  11. Hqupt K, Mosbach K (2000) Molecularly imprinted polymers and their use in biomi-metic sensors. Chem Rev 100:2495–2504

    Article  Google Scholar 

  12. Bitar A, Fessi H, Elaissari A (2012) Synthesis and characterization of thermally and glucose-sensitive poly N-vinylcaprolactam-based microgels. J Biomed Nanotechnol 8:709–719

    Article  CAS  Google Scholar 

  13. Lin ZA, Pang JL, Lin Y, Huang H, Cai ZW, Zhang L, Chen GN (2011) Preparation and evaluation of a phenylboronate affinity monolith for selective capture of glycoproteins by capillary liquid chromatography. Analyst 136:3281–3288

    Article  CAS  Google Scholar 

  14. Sellergren B, Lepistoe M, Mosbach K (1988) Highly enantioselective and substrate-selective polymers obtained by molecular imprinting utilizing noncovalent interactions. NMR and chromatographic studies on the nature of recognition. J Am Chem Soc 110:5853–5860

    Article  CAS  Google Scholar 

  15. Lee SH, Doong RA (2012) Adsorption and selective recognition of 17 β-estradiol by molecularly imprinted polymers. J Polym Res 19:9939

    Article  Google Scholar 

  16. Wulff G (1982) Selective binding to polymers via covalent bonds. Pure Appl Chem 54:2093–2102

    Article  Google Scholar 

  17. Wang X, Tang Q, Wang Q, Qiao X, Xu Z (2013) Study of a molecularly imprinted solid-phase extraction coupled with high-performance liquid chromatography for simultaneous determination of trace trichlorfon and monocrotophos residues in vegetables. J Sci Food Agric. doi:10.1002/jsfa.6429

    Google Scholar 

  18. Xu L, Xu ZF (2012) Molecularly imprinted polymer based on multiwalled carbon nanotubes for ribavirin recognition. J Polym Res 19:9942

    Article  Google Scholar 

  19. Xu L, He JF (2010) Preparation of hydrophilic molecularly imprinted nano-spheres and the properties on the drug release and recognition. Acta Scientiarum Natralium Universitatis Sunyatseni 49:61–64 (in Chinese)

    CAS  Google Scholar 

Download references

Acknowledgments

The authors were grateful to the National Natural Science Foundation of China (No, 81303199) and Distinguished Young Talents in Higher Education of Guangdong, China (No, K5090006) for the financial support to the research.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jian-feng He.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yang, Wl., Huang, Sm., Wu, Qz. et al. Properties evaluation and separation application of naringin-imprinted polymers prepared by a covalent imprinting method based on boronate ester. J Polym Res 21, 383 (2014). https://doi.org/10.1007/s10965-014-0383-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-014-0383-x

Keywords

Navigation