Skip to main content
Log in

Duo-molecularly imprinted polymer-coated magnetic particles for class-selective removal of endocrine-disrupting compounds from aqueous environment

  • Research Article
  • Published:
Environmental Science and Pollution Research Aims and scope Submit manuscript

Abstract

The removal of steroid and phenolic endocrine-disrupting compounds (EDCs) from an aqueous environment was investigated using magnetic particles encapsulated by a duo-molecularly imprinted polymer (duo-MIP). The effect of environmental variables on the binding efficiency was studied. Experimental results showed that the amount of EDCs adsorbed was neither affected by up to 10.0 mM NaCl nor significantly interfered by up to 10.0 mg/L humic acid. Negligible influence was observed from pH 3.3 to pH 6.8, but a decrease started at pH 9. Freundlich isotherm parameters indicated binding capacities in the order of DES > E2 ∼ E1 > BPA. The applicability of class-selective removal was verified using river water samples spiked with these EDCs at 10 μg/L; the binding efficiencies were 90, 90, 88, and 98 % for estrone (E1), 17β-estradiol (E2), bisphenol A (BPA), and diethylstilbestrol (DES), respectively. A reuse investigation verified constant binding capacities exhibiting <2 % reduction after seven cycles of regeneration.

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.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  • Alsudir S, Iqbal Z, Lai EPC (2012) Rapid CE-UV binding tests for selective recognition of bisphenol A by molecularly imprinted polymer particles. Electrophoresis 33(8):1255–1262

    Article  CAS  Google Scholar 

  • Auriol M, Filali-Meknassi Y, Tyagi RD, Adams CD, Surampalli RY (2006) Endocrine disrupting compounds removal from wastewater, a new challenge. Process Biochem 41(3):525–539. doi:10.1016/j.procbio.2005.09.017

    Article  CAS  Google Scholar 

  • Bravo JC, Garcinuno RM, Fernandez P, Durand JS (2007) A new molecularly imprinted polymer for the on-column solid-phase extraction of diethylstilbestrol from aqueous samples. Anal Bioanal Chem 388(5–6):1039–1045. doi:10.1007/s00216-007-1219-x

    Article  CAS  Google Scholar 

  • Bui BTS, Haupt K (2010) Molecularly imprinted polymers: synthetic receptors in bioanalysis. Anal Bioanal Chem 398:2481–2492

    Article  CAS  Google Scholar 

  • Campbell CG, Borglin SE, Green FB, Grayson A, Wozei E, Stringfellow WT (2006) Biologically directed environmental monitoring, fate, and transport of estrogenic endocrine disrupting compounds in water: a review. Chemosphere 65(8):1265–1280. doi:10.1016/j.chemosphere.2006.08.003

    Article  CAS  Google Scholar 

  • Chen LX, Xu SF, Li J (2011) Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. Chem Soc Rev 40(5):2922–2942

    Article  CAS  Google Scholar 

  • Clara M, Strenn B, Saracevic E, Kreuzinger N (2004) Adsorption of bisphenol-A, 17 beta-estradiole and 17 alpha-ethinylestradiole to sewage sludge. Chemosphere 56(9):843–851. doi:10.1016/j.chemosphere.2004.04.048

    Article  CAS  Google Scholar 

  • Daughton CG (2001) Emerging pollutants, and communicating the science of environmental chemistry and mass spectrometry: pharmaceuticals in the environment. J Am Soc Mass Spectrom 12(10):1067–1076. doi:10.1016/S1044-0305(01)00287-2

    Article  CAS  Google Scholar 

  • DeMaleki Z, Lai EPC, Dabek-Zlotorzynska E (2010) Capillary electrophoresis characterization of molecularly imprinted polymer particles in fast binding with 17β-estradiol. J Sep Sci 116(3):2796–2803

    Article  Google Scholar 

  • Durairaj C, Kim SJ, Edelhauser HF, Shah JC, Kompella UB (2009) Influence of dosage form on the intravitreal pharmacokinetics of diclofenac. Investig Ophthalmol Vis Sci 50(10):4887–4897. doi:10.1167/iovs.09-3565

    Article  Google Scholar 

  • Esplugas S, Bila DM, Krause LGT, Dezotti M (2007) Ozonation and advanced oxidation technologies to remove endocrine disrupting chemicals (EDCs) and pharmaceuticals and personal care products (PPCPs) in water effluents. J Hazard Mater 149(3):631–642. doi:10.1016/j.jhazmat.2007.07.073

    Article  CAS  Google Scholar 

  • Fowler PA, Bellingham M, Sinclair KD, Evans NP, Pocar P, Fischer B, Schaedlich K, Schmidt J-S, Amezaga MR, Bhattacharya S, Rhind SM, O'Shaughnessy PJ (2012) Impact of endocrine-disrupting compounds (EDCs) on female reproductive health. Mol Cell Endocrinol 355(2):231–239. doi:10.1016/j.mce.2011.10.021

    Article  CAS  Google Scholar 

  • Giger W, Gabriel FLP, Jonkers N, Wettstein FE, Kohler HPE (2009) Environmental fate of phenolic endocrine disruptors: field and laboratory studies. Philos Trans R Soc A Math Phys Eng Sci 367(1904):3941–3963. doi:10.1098/rsta.2009.0148

    Article  CAS  Google Scholar 

  • Herrero-Hernandez E, Carabias-Martinez R, Rodriguez-Gonzalo E (2011) Behavior of phenols and phenoxyacids on a bisphenol-A imprinted polymer. Application for selective solid-phase extraction from water and urine samples. Int J Mol Sci 12(5):3322–3339. doi:10.3390/ijms12053322

    Article  CAS  Google Scholar 

  • Huang B, Bai F, Yang XL, Huang WQ (2010) Synthesis of monodisperse hollow polymer microspheres with functional groups by distillation precipitation polymerization. Chin J Polym Sci 28(2):227–285. doi:10.1007/s10118-010-9089-7

    Article  Google Scholar 

  • Janos P, Buchtova H, Ryznarova M (2003) Sorption of dyes from aqueous solutions onto fly ash. Water Res 37(20):4938–4944. doi:10.1016/j.watres.2003.08.011

    Article  CAS  Google Scholar 

  • Khasanah M, Mudasir M, Kuncaka A, Sugiharto E, Supriyanto G, Wafiroh S (2010) Enhancement of the sensitivity and selectivity of the voltammetric sensor for uric acid using molecularly imprinted polymer. Indones J Chem 10(3):290–294

    Google Scholar 

  • Kong JH, Wang YZ, Nie C, Ran D, Jia XP (2012) Preparation of magnetic mixed-templates molecularly imprinted polymer for the separation of tetracycline antibiotics from egg and honey samples. Anal Methods 4(4):1005–1011. doi:10.1039/C2AY05662C

    Article  CAS  Google Scholar 

  • Lasakova M, Jandera P (2009) Molecularly imprinted polymers and their application in solid phase extraction. J Sep Sci 32(5–6):799–812. doi:10.1002/jssc.200800506

    CAS  Google Scholar 

  • Li Y, Dong CK, Chu J, Qi JY, Li X (2011) Surface molecular imprinting onto fluorescein-coated magnetic nanoparticles via reversible addition fragmentation chain transfer polymerization: a facile three-in-one system for recognition and separation of endocrine disrupting chemicals. Nanoscale 3(1):280–287. doi:10.1039/c0nr00614a

    Article  CAS  Google Scholar 

  • Lin Y, Shi Y, Jiang M, Jin Y, Peng Y, Lu B, Dai K (2008) Removal of phenolic estrogen pollutants from different sources of water using molecularly imprinted polymeric microspheres. Environ Pollut 153(2):483–491. doi:10.1016/j.envpol.2007.08.001

    Article  CAS  Google Scholar 

  • Magi E, Di Carro M, Liscio C (2010) Passive sampling and stir bar sorptive extraction for the determination of endocrine-disrupting compounds in water by GC-MS. Anal Bioanal Chem 397(3):1335–1345. doi:10.1007/s00216-010-3656-1

    Article  CAS  Google Scholar 

  • Matozzo V, Gagne F, Marin MG, Ricciardi F, Blaise C (2008) Vitellogenin as a biomarker of exposure to estrogenic compounds in aquatic invertebrates: a review. Environ Int 34(4):531–545. doi:10.1016/j.envint.2007.09.008

    Article  CAS  Google Scholar 

  • Meeker JD (2010) Exposure to environmental endocrine disrupting compounds and men's health. Maturitas 66(3):236–241. doi:10.1016/j.maturitas.2010.03.001

    Article  CAS  Google Scholar 

  • Meng Z, Chen W, Mulchandani A (2005) Removal of estrogenic pollutants from contaminated water using molecularly imprinted polymers. Environ Sci Technol 39:8958–8962

    Article  CAS  Google Scholar 

  • Mills LJ, Chichester C (2005) Review of evidence: are endocrine-disrupting chemicals in the aquatic environment impacting fish populations? Sci Total Environ 343(1–3):1–34. doi:10.1016/j.scitotenv.2004.12.070

    Article  CAS  Google Scholar 

  • Murray A, Örmeci 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(9):3820–3830

    Article  CAS  Google Scholar 

  • Pacakova V, Loukotkova L, Bosakova Z, Stulik K (2009) Analysis for estrogens as environmental pollutants—a review. J Sep Sci 32(5–6):867–882. doi:10.1002/jssc.200800673

    CAS  Google Scholar 

  • Suedee R, Seechamnanturakit V, Suksuwan A, Canyuk B (2008) Recognition properties and competitive assays of a dual dopamine/serotonin selective molecularly imprinted polymer. Int J Mol Sci 9(12):2333–2356. doi:10.3390/ijms9122333

    Article  CAS  Google Scholar 

  • Sun YK, Gu CG, Liu X, Liang WZ, Yao P, Bolton JL, van Breemen RB (2005) Ultrafiltration tandem mass spectrometry of estrogens for characterization of structure and affinity for human estrogen receptors. J Am Soc Mass Spectrom 16(2):271–279. doi:10.1016/j.jasms.2004.11.002

    Article  CAS  Google Scholar 

  • van de Kreeke J, de la Calle B, Held A, Bercaru O, Ricci M, Shegunova P, Taylor P (2010) IMEP-23: the eight EU-WFD priority PAHs in water in the presence of humic acid. TrAC Trends Anal Chem 29(8):928–937. doi:10.1016/j.trac.2010.04.009

    Article  Google Scholar 

  • Vasapollo G, Del Sole R, Mergola L, Lazzoi MR, Scardino A, Scorrano S, Mele G (2011) Molecularly imprinted polymers: present and future prospective. Int J Mol Sci 12(9):5908–5945. doi:10.3390/ijms12095908

    Article  CAS  Google Scholar 

  • Wang J, Li H, Yang X (2009) Preparation of hollow composite spheres with raspberry-like structure based on hydrogen-bonding interaction. Polym Adv Technol 20(12):965–971. doi:10.1002/pat.1349

    Article  Google Scholar 

  • Wang B, Huang B, Jin W, Wang Y, Zhao SM, Li FR, Hu P, Pan XJ (2012) Seasonal distribution, source investigation and vertical profile of phenolic endocrine disrupting compounds in Dianchi Lake, China. J Environ Monit 14(4):1275–1282. doi:10.1039/c2em10856a

    Article  Google Scholar 

  • Watabe Y, Kubo T, Nishikawa T, Fujita T, Kaya K, Hosoya K (2006) Fully automated liquid chromatography-mass spectrometry determination of 17 beta-estradiol in river water. J Chromatogr A 1120(1–2):252–259. doi:10.1016/j.chroma.2006.01.057

    CAS  Google Scholar 

  • Xia X, Lai EPC, Ormeci B (2012) Ultrasonication assisted synthesis of MIP-encapsulated magnetic nanoparticles for rapid and selective removal of 17β-estradiol from aqueous environment. Polym Eng Sci 52(8):1775–1783

    Article  CAS  Google Scholar 

  • Yang L, Li Z, Zou L, Gao H (2011) Removal capacity of pathways of phenolic endocrine disrupters in an estuarine wetland of natural reed bed. Chemosphere 88(3):233–239

    Article  Google Scholar 

  • Zhang Z, Hu J (2010) Effect of environmental factors on estrogenic compounds adsorption by MIP. Water Air Soil Pollut 210(1):255–264

    Article  CAS  Google Scholar 

  • Zhang JH, Jiang M, Zou LJ, Shi D, Mei SR, Zhu YX, Shi Y, Dai K, Lu B (2006) Selective solid-phase extraction of bisphenol A using molecularly imprinted polymers and its application to biological and environmental samples. Anal Bioanal Chem 385(4):780–786. doi:10.1007/s00216-006-0406-5

    Article  CAS  Google Scholar 

  • Zhou J, Chen Q, Wang YH, Fu YZ (2011) Stereospecific redox reaction of ascorbic acid and isoascorbic acid based on chiral electropolymerized films. Anal Methods 3(12):2740–2742. doi:10.1039/c1ay05428g

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was financially supported by the Canadian Water Network under the Innovative Treatment Technologies program.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Edward P. C. Lai.

Additional information

Responsible editor: Hongwen Sun

Rights and permissions

Reprints and permissions

About this article

Cite this article

Xia, X., Lai, E.P.C. & Örmeci, B. Duo-molecularly imprinted polymer-coated magnetic particles for class-selective removal of endocrine-disrupting compounds from aqueous environment. Environ Sci Pollut Res 20, 3331–3339 (2013). https://doi.org/10.1007/s11356-012-1262-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11356-012-1262-9

Keywords

Navigation