Magnetic Molecularly Imprinted Nanoparticles for the Solid-Phase Extraction of Diazinon from Aqueous Medium, Followed Its Determination by HPLC-UV

Document Type: Original Article

Authors

1 Applied Biotechnology Research Center, Baqiyatallah University of Medical Sciences, Tehran, Iran

2 Department of Chemistry, Faculty of Science, Zanjan University, Zanjan, Iran

Abstract

The aim of the present work was to investigate the feasibility of employing the molecular imprinting polymer technique for detecting diazinon using magnetic molecularly imprinted nanoparticles. The magnetic molecularly imprinted nanoparticles were prepared in the presence of a template diazinon molecule.  These nanoparticles exhibited a linear response in the range of 2-20 ppm (y= 0.2634×Cdiazinon - 0.0575, R2=0.9892) for detection of diazinon. The adsorption kinetics and isotherms and the selectivity efficiencies of diazinon and other structurally related analogues were investigated by HPLC-UV as well, respectively. The results showed that the magnetic molecularly imprinted nanoparticles have high adsorption capacity, controlled selectivity, and direct magnetic separation in aqueous environments. The results indicates that the spiked recoveries were changed from 73 to 85%, and the RSD was lower than 11.91.

Keywords


  1. Wulff, G., Molecular imprinting in cross-linked materials with the aid of molecular templates a way towards artificial antibodies. Angew Chem Int Ed Engl, 1995, Vol. 34, pp. 1812–1832.
  2. Steinke, J.H.G., Sherrington, D.C., Dunkin, I.R. Imprinting of synthetic polymers using molecular templates. Adv Polym Sci, 1995, Vol. 123, pp. 82–125.
  3. Shea, K.J., Spivak, D.A., Sellergren, B.J. Polymer complements to nucleotide bases. Selective binding of adenine derivatives to imprinted polymers. Am Chem Soc, 1993, Vol. 115, pp. 3368–3369.
  4. Vlatakis, G., Andersson, L.I., Muller, R., Mosbach, K. Drug assay using antibody mimics made by molecular imprinting. Nature, 1993, Vol. 361, pp. 645–647.
  5. Haupt, K., Mosbach, K. Molecularly imprinted polymers and their use in biomimetic sensors. Chem Rev, 2000, Vol. 100, pp. 2495-2504.
  6. Haupt, K. Peer reviewed: molecularly imprinted polymers: the next generation. Anal Chem, 2003, Vol. 75, pp. 376A–383A.
  7. Wulff, G. Enzyme-like Catalysis by Molecularly Imprinted Polymers. Chem Rev, 2002, Vol. 102, pp. 1-28.
  8. Ge, Y., Butler, B., Mirza, F., Habib-Ullah, S. Smart molecularly imprinted polymers: recent developments and applications. Macromol, 2013, Vol. 34, pp. 903-915.
  9. Cheong, W.J., Yang, S.H., Ali, F. Molecular imprinted polymers for separation science: a review of reviews. J Sep Sci, 2013, Vol. 36, pp. 609-628.
  10. Najafizadeh, P., Ebrahimi, S.A. Synthesis of a phenylalanine imprinted polymer for attenuation of phenylalanine absorption via the gut in a murine hyperphenylalaninemia model. J Mater Chem B, 2013, Vol. 2, pp. 2144-2152.
  11. Unluer, O.B., Ersoz, A., Denizli, A. Separation and purification of hyaluronic acid by embedded glucuronic acid imprinted polymers into cryogel. J Chromatogr B, 2013, Vol. 934, pp. 46-52.
  12. Li, B., Xu, J.J., Hall, A.J., Haupt, K. Water-compatible silica sol–gel molecularly imprinted polymer as a potential delivery system for the controlled release of salicylic acid. J Mol Recognit, 2014, Vol. 27, pp. 559-565.
  13. Lv, Y., Tan, T., Svec, F. Molecular imprinting of proteins in polymers attached to the surface of nano materials for selective recognition of biomacromolecules. Biotechnol Adv, 2013, Vol. 31, pp. 1172-1186.
  14. Davoodi, D., Khayyat, M.H., Mohajeri, S.A., Rezaei, M.A. Preparation, evaluation and application of diazinon imprinted polymers as the sorbent in molecularly imprinted solid-phase extraction and liquid chromatography analysis in cucumber and aqueous samples. Food Chemistry, 2014, Vol. 158, pp. 421-428.
  15. Bayat, M., Hassanzadeh-Khayyat, M., Mohajeri, S.A. Determination of diazinon pesticide residue in Tomato fruit and Tomato paste by molecularly imprinted solid-phase extraction coupled with liquid chromatography analysis. Food Anal Methods, 2015, Vol. 8, pp. 1034-1041.
  16. Alamgir, M., Chowdhury, Z., Bhattacharjee, Sh., Fakhruddin, A.N.M., Islam, M.N., Khorshed M. Determination of cypermethrin, chlorpyrifos and diazinon residues in Tomato and reduction of cypermethrin residues in Tomato using Rice bran. World JAgric Res, 2013, Vol. 1, pp. 30-35.
  17. Hernandez, F., Sancho, J.V., Pozo, O.J. Critical Review of the application of liquid chromatography to the determination of pesticide residues in biological samples. Anal Bioanal Chem, 2005, Vol. 382, pp. 934-946.
  18. Karimian, R., Piri, F. Synthesis and investigation the catalytic behavior of Cr2O3 nanoparticles. J Nanostruct, 2013, Vol. 3, pp. 87-92.
  19. Chen, J.,  Liang, R.P., Wang, X.N., Qiu, J.D.  A norepinephrine coated magnetic molecularly imprinted polymer for simultaneous multiple chiral recognition. J Chromatogr A, 2015, Vol. 1409, pp. 268–276.
  20. Hu, Y.L., Liu, R.J., Zhang, Li, G.K. Improvement of extraction capability of magnetic molecularly imprinted polymer beads in aqueous media via dual-phase solvent system. Talanta, 2009, Vol. 79, pp. 576–582.
  21. Chen, L.G., Liu, J., Zeng, Q.L., Wang, H., Yu, A.M., Zhang, H.Q., Ding, L. Preparation of magnetic molecularly imprinted polymer for the separation of tetracycline antibiotics from egg and tissue samples. J Chromatogr A, 2009, Vol. 1216, pp. 3710–3719.
  22. Li, Y., Li, X., Chu, J., Dong, C.K., Qi, J.Y., Yuan, Y.X. 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, 2010, Vol. 158, pp. 2317–2323.
  23. Chen, L., Li, B. Determination of imidacloprid in rice by molecularly imprinted-matrix solid-phase dispersion with liquid chromatography tandem mass spectrometry. J Chromatogr B, 2012, Vol. 897, pp. 32–36.
  24. Liu, Y., Huang, Y., Liu, J., Wang, W., Liu, G., Zhao. R. Superparamagnetic surface molecularly imprinted nanoparticles for water-soluble pefloxacin mesylate prepared via surface initiated atom transfer radical polymerization and its application in egg sample analysis. J Chromatogr A, 2012, Vol. 1246, pp. 15–21.
  25. Matsui, J., Miyoshi, Y., Doblhoff-Dier, O., Takeuchi, T. A molecularly imprinted synthetic polymer receptor selective for atrazine. Anal Chem, 1995, Vol. 67, pp. 4404–4408.
  26. Quaglia, M., Chenon, K., Hall, A.J., Lorenzi, E.D., Sellergren, B. Target Analogue Imprinted Polymers with Affinity for Folic Acid and Related Compounds. J Am Chem Soc, 2001, Vol. 123, pp. 2146–2154.
  27. Ikegami, T., Mukawa, T., Nariai, H., Takeuchi, T. Bisphenol A−recognition polymers prepared by covalent molecular imprinting. Anal Chim Acta, 2004, Vol. 504, pp. 131–135.
  28. Lu, Y.K., Yan, X.P. An Imprinted Organic−Inorganic Hybrid Sorbent for Selective Separation of Cadmium from Aqueous Solution. Anal Chem, 2004, Vol. 76, pp. 453-457.
  29. Chen, D., Deng, J., Liang, J., Xie, J., Huang, K., Hu, C. Core–shell magnetic nanoparticles with surface imprinted polymer coating as a new adsorbent forsolid phase extraction of metronidazole. Anal Methods, 2013, Vol. 5, pp. 722-728.