Skip to main content
SpringerLink
Log in

Tailor-made molecularly imprinted polymers for dimethoate and deltamethrin recognition: synthesis, characterization and chromatographic evaluation

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

Abstract

This work concerns the development of molecularly imprinted polymers (MIPs) for the selective extraction of dimethoate (dmt) and deltamethrin (dm) from food matrices. To achieve this goal, the non-covalent methodology has been applied for the preparation of MIPs using metacrylic acid (MAA) as a functional monomer and ethylene glycol dimethacrylate (EGDMA) and triethylene glycol dimethacrylate (TEGDMA) as cross-linkers in order to evaluate the influence of the nature of the cross-linker on the efficiency and selectivity of those MIPs for the target pesticides. Non-imprinted polymers (NIPs), which do not contain template, have been also prepared in parallel with the MIP synthesis using the same synthetic protocol to assess the specificity of the interactions. Chemical and physical characterization was carried out using conventional techniques, such as Fourier transform infrared (FTIR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy and thermogravimetric analysis (TGA). Morphological characterization of MIPs and NIPs has been also performed using scanning electron microscopy (SEM) in order to assess the polymer’s surface topography. The performance of each polymer was evaluated by conducting binding property measurements, namely imprinting factor determinations and adsorption studies using high performance liquid chromatography (HPLC). The results obtained in this study seem to show that there is a correlation between the polymer structure (including its physical characteristics) and their binding properties.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13

Similar content being viewed by others

References

  1. Bui BTSK (2010) Haupt Anal Bioanal Chem 398:2481–2492

    Article  CAS  Google Scholar 

  2. Vasapollo G, Del Sole R, Mergola L, Lazzoi MR, Scardino A, Scorrano S, Mele G (2011) Int J Mol Sci 12:5908–5945

    Article  CAS  Google Scholar 

  3. Garcia R, Cabrita MJ, Freitas AMC (2011) Am J Anal Chem 2:16–25

    Article  Google Scholar 

  4. García-Calzón JA, Díaz-García ME (2007) Sens and Actuators B 123:1180–1194

    Article  Google Scholar 

  5. Martín-Esteban A (2013) Trends Anal Chem 45:169–181

    Article  Google Scholar 

  6. Ansell RJ, Kriz D, Mosbach K (1996) Curr Opin Biotechnol 7:89–94

    Article  CAS  Google Scholar 

  7. Nunez O, Gallart-Ayala H, Martins CPB, Lucci P (2012) J Chromatogr A 1228:298–323

    Article  CAS  Google Scholar 

  8. Alexander C, Davidson L, Hayes W (2003) Tetrahedron 59:2025–2057

    Article  CAS  Google Scholar 

  9. Corma A (2004) Sci Eng 46:369–417

    CAS  Google Scholar 

  10. Kloskowski A, Pilarczyk M, Przyjazny A, Namiesnik J (2009) Anal Chem 39:43–58

    CAS  Google Scholar 

  11. Augusto F, Carasek E, Silva RGC, Rivellino SR, Batista AD, Martendal E (2010) J Chrom A 1217:2533–2542

    Article  CAS  Google Scholar 

  12. Beltran A, Borrull F, Marcé RM (2010) TrAC Trends Anal Chem 29:1363–1375

    Article  CAS  Google Scholar 

  13. Hu Y, Pan J, Zhang K, Lian H, Li G (2013) TrAC Trends Anal Chem 43:37–52

    Article  CAS  Google Scholar 

  14. Moreno-Bondi MC, Navarro-Villoslada F, Benito-Pena E, Urraca JL (2008) Curr Anal Chem 4:316–340

    Article  CAS  Google Scholar 

  15. Shimizu KD, Stephenson CJ (2010) Curr Opin Chem Biol 14:743–750

    Article  CAS  Google Scholar 

  16. Malitesta C, Mazzotta E, Picca R, Poma A, Chianella I, Piletsky S (2012) Anal Bioanal Chem 402:1827–1846

    Article  CAS  Google Scholar 

  17. Cunliffe D, Kirby A, Alexander C (2005) Adv Drug Delivery Reviews 57:1836–1853

    CAS  Google Scholar 

  18. Rathbone DL (2005) Adv Drug Delivery Reviews 57:1854–1874

    Article  CAS  Google Scholar 

  19. Regulation (EC) No. 396/2005 of the European Parliament and of the council of 23 February 2005 on maximum residue levels of pesticides in or on food and feed of plant and animal origin and amending Council Directive 91/414/EEC, and subsequent updates, http://ec.europa.eu/food/plant/protection/pesticides/inex_en.htm. and Codex Alimentarius Committee on Pesticide Residues, Joint FAO/WHO Meeting on Pesticide Residues (last update 2009) http://www.codexalimentarius.net/mrls/pestdes/jsp/pest_q-e.jsp

  20. Anastassiades M, Lehotay SJ, Stajnbaher D, Schenck FJ (2003) J AOAC Int 86:412–431

    CAS  Google Scholar 

  21. Wilkowska A, Biziuk M (2011) Food Chem 125:803–812

    Article  CAS  Google Scholar 

  22. Okutucu B, Onal S (2011) Talanta 87:74–79

    Article  CAS  Google Scholar 

  23. Pichon V, Chapuis-Hugon F (2008) Anal Chim Acta 622:48–61

    Article  CAS  Google Scholar 

  24. Chapuis F, Pichon V, Lanza F, Sellergren B, Hennion MC (2004) J Chromatogr B 804:93–101

    Article  CAS  Google Scholar 

  25. Tom LA, Schneck NA, Walter C (2012) J Chromatogr B 909:61–64

    Article  CAS  Google Scholar 

  26. Xu S, Li J, Chen L (2011) Talanta 85:282–343

    Article  CAS  Google Scholar 

  27. Matsui J, Kubo H, Takeuchi T (1998) Anal Sci 14:699–702

    Article  CAS  Google Scholar 

  28. Siemann M, Andersson LI, Mosbach K (1998) J Agric Food Chem 44:141–145

    Article  Google Scholar 

  29. Piletska EV, Guerreiro AR, Whitcombe MJ, Piletsky SA (2009) Macromolecules 42:4921–4928

    Article  CAS  Google Scholar 

  30. Martin P, Jones GR, Stringer F, Wilson ID (2003) Analyst 128:345–181

    Article  CAS  Google Scholar 

  31. Andersson LI, Paprica A, Arvidsson T (1997) Chromatographia 46:57–66

    Article  CAS  Google Scholar 

  32. López MMC, Pérez MCC, García MSD, Vilarino JML, Rodríguez MVG, Losada L-FB (2012) Anal Chim Acta 721:68–78

    Article  Google Scholar 

  33. Holland N, Frisby J, Owens E, Hughes H, Duggan P, McLoughlin P (2010) Polymer 51:1578–1584

    Article  CAS  Google Scholar 

  34. Tang K, Chen S, Gu X, Wang H, Dai J, Tang J (2008) Anal Chim Acta 614:112–118

    Article  CAS  Google Scholar 

  35. Xu ZF, Wen G, Kuang DZ, Zhang FX, Tang SP (2013) J Environ Sci Health Part B 48:336–343

    Article  CAS  Google Scholar 

  36. Bakas I, Oujji NB, Moczko E, Istamboulie G, Piletsky S, Piletska E, Ait-Ichou I, Ait-Addi E, Noguer Rouillon TR (2013) J Chromatogr A 1274:13–18

    Article  CAS  Google Scholar 

  37. Lv Y, Lin Z, Feng W, Zhou X, Tan T (2007) Biochem Eng J 36:221–229

    Article  CAS  Google Scholar 

  38. Pap T, Horvai G (2004) J Chromatogr B 804:167–172

    Article  CAS  Google Scholar 

  39. Corton E, García-Calzón JA, Díaz-García ME (2007) J Non-Cryst Solids 353:974–980

    Article  CAS  Google Scholar 

  40. Umpleby RJ II, Baxter SC, Bode M, Berch JK Jr, Shah RN, Shimizu KD (2001) Anal Chim Acta 435:35–42

    Article  CAS  Google Scholar 

  41. Rampey AM, Umpleby RJ, Rushton GT, Iseman JC, Shah RN, Shimizu KD (2004) Anal Chem 76:1123–1133

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work is funded by FEDER Funds through the Operational Programme for Competitiveness Factors–COMPETE and National Funds through FCT–Foundation for Science and Technology under the Strategic Projects PEst-C/Agr/UI0115/2011 and PEst-OE/QUI/UI0619/2011 and Project PTDC/AGR-ALI/117544/2010. Prof. Peter Carrott and Ms. Louisa Marques are acknowledged for their assistance with the TGA study. Laboratory HERCULES at the University of Évora is acknowledged for the SEM analyses. Prof. João Rocha and the solid state NMR service at CICECO, University of Aveiro, Portugal are thanked for the solid state MAS-31P NMR study.

Author information

Authors and Affiliations

  1. Departamento de Química e Centro de Química de Évora, Universidade de Évora, Rua Romão Ramalho, 59 7000, Évora, Portugal

    Marco Simões & Anthony J. Burke

  2. ICAAM–Instituto de Ciências Agrárias e Ambientais Mediterrânicas, Universidade de Évora, Núcleo da Mitra, Ap. 94, 7002-554, Évora, Portugal

    Nuno Martins, Maria João Cabrita & Raquel Garcia

Authors
  1. Marco Simões
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nuno Martins
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Maria João Cabrita
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Anthony J. Burke
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Raquel Garcia
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Raquel Garcia.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Simões, M., Martins, N., Cabrita, M.J. et al. Tailor-made molecularly imprinted polymers for dimethoate and deltamethrin recognition: synthesis, characterization and chromatographic evaluation. J Polym Res 21, 368 (2014). https://doi.org/10.1007/s10965-014-0368-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-014-0368-9

Keywords

Search

Navigation