Environmental Science and Pollution Research

, Volume 20, Issue 5, pp 3331–3339 | Cite as

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

Research Article
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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.

Keywords

Endocrine-disrupting compounds Aqueous environment Class-selective removal Molecularly imprinted polymer Duo template Magnetic particles 
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Notes

Acknowledgments

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

References

  1. 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):1255–1262CrossRefGoogle Scholar
  2. 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 CrossRefGoogle Scholar
  3. 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 CrossRefGoogle Scholar
  4. Bui BTS, Haupt K (2010) Molecularly imprinted polymers: synthetic receptors in bioanalysis. Anal Bioanal Chem 398:2481–2492CrossRefGoogle Scholar
  5. 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 CrossRefGoogle Scholar
  6. Chen LX, Xu SF, Li J (2011) Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. Chem Soc Rev 40(5):2922–2942CrossRefGoogle Scholar
  7. 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 CrossRefGoogle Scholar
  8. 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 CrossRefGoogle Scholar
  9. 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):2796–2803CrossRefGoogle Scholar
  10. 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 CrossRefGoogle Scholar
  11. 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 CrossRefGoogle Scholar
  12. 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 CrossRefGoogle Scholar
  13. 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 CrossRefGoogle Scholar
  14. 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 CrossRefGoogle Scholar
  15. 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 CrossRefGoogle Scholar
  16. 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 CrossRefGoogle Scholar
  17. 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):290–294Google Scholar
  18. 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 CrossRefGoogle Scholar
  19. 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 Google Scholar
  20. 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 CrossRefGoogle Scholar
  21. 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 CrossRefGoogle Scholar
  22. 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 CrossRefGoogle Scholar
  23. 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 CrossRefGoogle Scholar
  24. 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 CrossRefGoogle Scholar
  25. Meng Z, Chen W, Mulchandani A (2005) Removal of estrogenic pollutants from contaminated water using molecularly imprinted polymers. Environ Sci Technol 39:8958–8962CrossRefGoogle Scholar
  26. 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 CrossRefGoogle Scholar
  27. 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):3820–3830CrossRefGoogle Scholar
  28. 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 Google Scholar
  29. 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 CrossRefGoogle Scholar
  30. 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 CrossRefGoogle Scholar
  31. 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 CrossRefGoogle Scholar
  32. 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 CrossRefGoogle Scholar
  33. 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 CrossRefGoogle Scholar
  34. 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 CrossRefGoogle Scholar
  35. 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 Google Scholar
  36. 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):1775–1783CrossRefGoogle Scholar
  37. 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):233–239CrossRefGoogle Scholar
  38. Zhang Z, Hu J (2010) Effect of environmental factors on estrogenic compounds adsorption by MIP. Water Air Soil Pollut 210(1):255–264CrossRefGoogle Scholar
  39. 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 CrossRefGoogle Scholar
  40. 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 CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2012

Authors and Affiliations

  1. 1.Department of ChemistryCarleton UniversityOttawaCanada
  2. 2.Department of Civil and Environmental EngineeringCarleton UniversityOttawaCanada

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