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Analytical and Bioanalytical Chemistry

, Volume 407, Issue 6, pp 1735–1744 | Cite as

Development and characterization of magnetic molecularly imprinted polymers for the selective enrichment of endocrine disrupting chemicals in water and milk samples

  • Xiaoyu Xie
  • Xiaoyan Pan
  • Shengli Han
  • Sicen WangEmail author
Research Paper

Abstract

Analyses of four endocrine disrupting chemicals (EDCs) in water and milk samples were undertaken by using magnetic molecularly imprinted polymers (MMIPs). These were prepared via the surface molecular imprinting technique using super paramagnetic core-shell nanoparticle as support. Diethylstilbestrol (DES), which is a typical EDC, was employed as the template molecule. The obtained MMIPs were characterized using transmission electron microscope, Fourier transform infrared, X-ray diffraction, and vibrating sample magnetometer. Accordingly, the adsorption capacity and selectivity of prepared MMIPs were investigated. The binding isotherms were obtained for DES and fitted by the Freundlich isotherm model. A corresponding analytical method to determine four EDCs was developed. The recoveries of the spiked samples in pond water and pure milk range from 67.8 to 93.2 % and from 65.3 to 92.5 %, respectively. Coupled with high-performance liquid chromatography analysis, the prepared MMIPs were successfully applied to the analysis of EDCs in water and milk samples.

Graphical Abstract

The construction and feature of magnetic molecularly imprinted polymers

Keywords

Molecularly imprinted polymers Super paramagnetic Endocrine disrupting chemicals Water and milk 

Notes

Acknowledgments

This work was financially supported by National Natural Science Foundation of China (81227802), the China Postdoctoral Science Foundation (2014 M550501), and the Fundamental Research Funds for the Central Universities (xjj2014066).

Supplementary material

216_2014_8425_MOESM1_ESM.pdf (400 kb)
ESM 1 (PDF 400 kb)

References

  1. 1.
    Ahmadi F, Yawari E, Nikbakht M (2014) Computational design of an enantioselective molecular imprinted polymer for the solid phase extraction of S-warfarin from plasma. J Chromatogr A 1338:9–16CrossRefGoogle Scholar
  2. 2.
    Blasco B, Pico Y (2012) Development of an improved method for trace analysis of quinolones in eggs of laying hens and wildlife species using molecularly imprinted polymers. J Agric Food Chem 60:11005–11014CrossRefGoogle Scholar
  3. 3.
    Chen FF, Wang R, Shi YP (2012) Molecularly imprinted polymer for the specific solid-phase extraction of kirenol from Siegesbeckia pubescens herbal extract. Talanta 89:505–512CrossRefGoogle Scholar
  4. 4.
    Sadeghi S, Jahani M (2013) Selective solid-phase extraction using molecular imprinted polymer sorbent for the analysis of Florfenicol in food samples. Food Chem 141:1242–1251CrossRefGoogle Scholar
  5. 5.
    Vlatakis G, Andersson LI, Muller R, Mosbach K (1993) Drug assay using antibody mimics made by molecular imprinting. Nature 361:645–647CrossRefGoogle Scholar
  6. 6.
    Wulff G (2002) Enzyme-like catalysis by molecularly imprinted polymers. Chem Rev 102:1–27CrossRefGoogle Scholar
  7. 7.
    Tiwari MP, Prasad BB (2014) An insulin monitoring device based on hyphenation between molecularly imprinted micro-solid phase extraction and complementary molecularly imprinted polymer-sensor. J Chromatogr A 1337:22–31CrossRefGoogle Scholar
  8. 8.
    Barrios CA, Zhenhe C, Navarro-Villoslada F, Lopez-Romero D, Moreno-Bondi MC (2011) Molecularly imprinted polymer diffraction grating as label-free optical bio(mimetic)sensor. Biosens Bioelectron 26:2801–2804CrossRefGoogle Scholar
  9. 9.
    Rodriguez E, Navarro-Villoslada F, Benito-Pena E, Marazuela MD, Moreno-Bondi MC (2011) Multiresidue determination of ultratrace levels of fluoroquinolone antimicrobials in drinking and aquaculture water samples by automated online molecularly imprinted solid phase extraction and liquid chromatography. Anal Chem 83:2046–2055CrossRefGoogle Scholar
  10. 10.
    Pakade V, Lindahl S, Chimuka L, Turner C (2012) Molecularly imprinted polymers targeting quercetin in high-temperature aqueous solutions. J Chromatogr A 1230:15–23CrossRefGoogle Scholar
  11. 11.
    Xu SX, Zhang XF, Sun YH, Yu D (2013) Microwave-assisted preparation of monolithic molecularly imprinted polymeric fibers for solid phase microextraction. Analyst 138:2982–2987CrossRefGoogle Scholar
  12. 12.
    Li Y, Li X, Chu J, Dong CK, Qi JY, Yuan YX (2010) Synthesis of core-shell magnetic molecular imprinted polymer by the surface RAFT polymerization for the fast and selective removal of endocrine disrupting chemicals from aqueous solutions. Environ Pollut 158:2317–2323CrossRefGoogle Scholar
  13. 13.
    Chen FF, Wang GY, Shi YP (2011) Molecularly imprinted polymer microspheres for solid-phase extraction of protocatechuic acid in Rhizoma homalomenae. J Sep Sci 34:2602–2610CrossRefGoogle Scholar
  14. 14.
    Ramstrom O, Skudar K, Haines J, Patel P, Bruggemann O (2001) Food analyses using molecularly imprinted polymers. J Agric Food Chem 49:2105–2114CrossRefGoogle Scholar
  15. 15.
    Chen LX, Xu SF, Li JH (2011) Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. Chem Soc Rev 40:2922–2942CrossRefGoogle Scholar
  16. 16.
    Wang XY, Kang Q, Shen DZ, Zhang Z, Li JH, Chen LX (2014) Novel monodisperse molecularly imprinted shell for estradiol based on surface imprinted hollow vinyl-SiO2 particles. Talanta 124:7–13CrossRefGoogle Scholar
  17. 17.
    Chen HC, Yuan DY, Li YY, Dong MJ, Chai ZH, Kong J, Fu GQ (2013) Silica nanoparticle supported molecularly imprinted polymer layers with varied degrees of crosslinking for lysozyme recognition. Anal Chim Acta 779:82–89CrossRefGoogle Scholar
  18. 18.
    Yang WJ, Jiao FP, Zhou L, Chen XQ, Jiang XY (2013) Molecularly imprinted polymers coated on multi-walled carbon nanotubes through a simple indirect method for the determination of 2,4-dichlorophenoxyacetic acid in environmental water. Appl Surf Sci 284:692–699CrossRefGoogle Scholar
  19. 19.
    Puoci F, Hampel S, Parisi OI, Hassan A, Cirillo G, Picci N (2013) Imprinted microspheres doped with carbon nanotubes as novel electroresponsive drug-delivery systems. J Appl Polym Sci 130:829–834CrossRefGoogle Scholar
  20. 20.
    Xu WZ, Zhou W, Xu PP, Pan JM, Wu XY, Yan YS (2011) A molecularly imprinted polymer based on TiO2 as a sacrificial support for selective recognition of dibenzothiophene. Chem Eng J 172:191–198CrossRefGoogle Scholar
  21. 21.
    Wang XH, Chen LR, Xu XJ, Li YZ (2011) Synthesis of molecularly imprinted polymers via ring-opening metathesis polymerization for solid-phase extraction of bisphenol A. Anal Bioanal Chem 401:1423–1432CrossRefGoogle Scholar
  22. 22.
    Xie LJ, Jiang RF, Zhu F, Liu H, Ouyang GF (2014) Application of functionalized magnetic nanoparticles in sample preparation. Anal Bioanal Chem 406:377–399CrossRefGoogle Scholar
  23. 23.
    Zhao M, Zhang C, Zhang Y, Guo XZ, Yan HS, Zhang HQ (2014) Efficient synthesis of narrowly dispersed hydrophilic and magnetic molecularly imprinted polymer microspheres with excellent molecular recognition ability in a real biological sample. Chem Commun 50:2208–2210CrossRefGoogle Scholar
  24. 24.
    Li DY, He XW, Chen Y, Li WY, Zhang YK (2013) Novel hybrid structure silica/CdTe/molecularly imprinted polymer: synthesis, specific recognition, and quantitative fluorescence detection of bovine hemoglobin. Acs Appl Mater Inter 5:12609–12616CrossRefGoogle Scholar
  25. 25.
    Li Y, Ding MJ, Wang S, Wang RY, Wu XL, Wen TT, Yuan LH, Dai P, Lin YH, Zhou XM (2011) Preparation of imprinted polymers at surface of magnetic nanoparticles for the selective extraction of tadalafil from medicines. Acs Appl Mater Inter 3:3308–3315CrossRefGoogle Scholar
  26. 26.
    Yao GH, Liang RP, Huang CF, Wang Y, Qiu JD (2013) Surface plasmon resonance sensor based on magnetic molecularly imprinted polymers amplification for pesticide recognition. Anal Chem 85:11944–11951CrossRefGoogle Scholar
  27. 27.
    Kong X, Gao RX, He XW, Chen LX, Zhang YK (2012) Synthesis and characterization of the core-shell magnetic molecularly imprinted polymers (Fe3O4@MIPs) adsorbents for effective extraction and determination of sulfonamides in the poultry feed. J Chromatogr A 1245:8–16CrossRefGoogle Scholar
  28. 28.
    Wang XH, Fang QX, Liu SP, Chen L (2012) Preparation of a magnetic molecularly imprinted polymer with pseudo template for rapid simultaneous determination of cyromazine and melamine in bio-matrix samples. Anal Bioanal Chem 405:5843–5852Google Scholar
  29. 29.
    Madrakian T, Afkhami A, Mahmood-Kashani H, Ahmadi M (2013) Superparamagnetic surface molecularly imprinted nanoparticles for sensitive solid-phase extraction of tramadol from urine samples. Talanta 105:255–261CrossRefGoogle Scholar
  30. 30.
    Vandenberg LN, Colborn T, Hayes TB, Heindel JJ, Jacobs DR, Lee DH, Shioda T, Soto AM, Vom Saal FS, Welshons WV, Zoeller RT, Myers JP (2012) Hormones and endocrine-disrupting chemicals: low-dose effects and nonmonotonic dose responses. Endocr Rev 33:378–455CrossRefGoogle Scholar
  31. 31.
    Wen YY, Li JH, Liu JS, Lu WH, Ma JP, Chen LX (2013) Dual cloud point extraction coupled with hydrodynamic-electrokinetic two-step injection followed by micellar electrokinetic chromatography for simultaneous determination of trace phenolic estrogens in water samples. Anal Bioanal Chem 405:5843–5852CrossRefGoogle Scholar
  32. 32.
    Giusti RM, Iwamoto K, Hatch EE (1995) Diethylstilbestrol revisited-a review of the long-term health-effects. Ann Intern Med 122:778–788CrossRefGoogle Scholar
  33. 33.
    Giese RW (2003) Measurement of endogenous estrogens: analytical challenges and recent advances. J Chromatogra A 1000:401–412CrossRefGoogle Scholar
  34. 34.
    Xue JQ, Li DW, Qu LL, Long YT (2013) Surface-imprinted core-shell Au nanoparticles for selective detection of bisphenol A based on surface-enhanced Raman scattering. Anal Chim Acta 777:57–62CrossRefGoogle Scholar
  35. 35.
    Hu C, He M, Chen BB, Hu B (2012) Determination of estrogens in pork and chicken samples by stir bar sorptive extraction combined with high-performance liquid chromatography-ultraviolet detection. J Agric Food Chem 60:10494–10500CrossRefGoogle Scholar
  36. 36.
    Xia XL, Lai EPC, Ormeci B (2013) Duo-molecularly imprinted polymer-coated magnetic particles for class-selective removal of endocrine-disrupting compounds from aqueous environment. Environ Sci Pollut Res 20:3331–3339CrossRefGoogle Scholar
  37. 37.
    Murray A, Ormeci B (2012) Application of molecularly imprinted and non-imprinted polymers for removal of emerging contaminants in water and wastewater treatment: a review. Environ Sci Pollut Res 19:3820–3830CrossRefGoogle Scholar
  38. 38.
    Ning FJ, Peng HL, Li JH, Chen LX, Xiong H (2014) Molecularly imprinted polymer on magnetic graphene oxide for fast and selective extraction of 17β-estradiol. J Agric Food Chem 62:7436–7443CrossRefGoogle Scholar
  39. 39.
    Lan HZ, Gan N, Pan DD, Hu FT, Li TH, Long NB, Qiao L (2014) An automated solid-phase microextraction method based on magnetic molecularly imprinted polymer as fiber coating for detection of trace estrogens in milk powder. J Chromatogr A 1331:10–18CrossRefGoogle Scholar
  40. 40.
    Zhang HF, Shi YP (2012) Magnetic retrieval of chitosan: extraction of bioactive constituents from green tea beverage samples. Analyst 137:910–916CrossRefGoogle Scholar
  41. 41.
    Lu FG, Li HJ, Sun M, Fan LL, Qiu HM, Li XJ, Luo CN (2012) Flow injection chemiluminescence sensor based on core-shell magnetic molecularly imprinted nanoparticles for determination of sulfadiazine. Anal Chim Acta 718:84–91CrossRefGoogle Scholar
  42. 42.
    Jiang XM, Zhao CD, Jiang N, Zhang HX, Liu MC (2008) Selective solid-phase extraction using molecular imprinted polymer for the analysis of diethylstilbestrol. Food Chem 108:1061–1067CrossRefGoogle Scholar
  43. 43.
    Liu MH, Li MJ, Qiu B, Chen X, Chen GN (2010) Synthesis and applications of diethylstilbestrol-based molecularly imprinted polymer-coated hollow fiber tube. Anal Chim Acta 663:33–38CrossRefGoogle Scholar
  44. 44.
    Zhao CD, Ji YS, ShaoYL JXM, Zhang HX (2009) Novel molecularly imprinted polymer prepared by nanoattapulgite as matrix for selective solid-phase extraction of diethylstilbestrol. J Chromatogr A 1216:7546–7552CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2015

Authors and Affiliations

  • Xiaoyu Xie
    • 1
  • Xiaoyan Pan
    • 1
  • Shengli Han
    • 1
  • Sicen Wang
    • 1
    Email author
  1. 1.School of Pharmacy, Health Science CenterXi’an Jiaotong UniversityXi’anChina

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