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Surface molecular imprinting for chemiluminescence detection of the organophosphate pesticide chlorpyrifos

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Abstract

We report on a surface molecular imprinting strategy for synthesizing core-shell particles whose shell is imprinted with chlorpyrifos (CPF). The particles were prepared by copolymerization of the methacryloyl groups on the surface of silica particles modified with 3-methacryloxypropyl trimethoxysilane a functional monomer and a cross-linking agent. The imprinted particles exhibit larger binding capacity, faster binding kinetics, and higher recognition selectivity for CPF. Combined with highly sensitive chemiluminescence assay, the method was applied to the determination of CPF with a detection limit of 0.92 nM which is about 2 orders of magnitude lower than that by conventional CL method. The method also displays repeatability for more than 200 times.

Schematic illustration of a surface molecular imprinting strategy for synthesizing core-shell particles with CPF-imprinted shells and the CL kinetics curves of MIP-based CL method for the determination of chlorpyrifos.

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References

  1. Banks KE, Hunter DH, Wachal DJ (2005) Chlorpyrifos in surface waters before and after a federally mandated ban. Environ Int 31:351–356

    Article  CAS  Google Scholar 

  2. Sinha SN, Pal R, Dewan A, Mansuri MM, Saiyed HN (2006) Effect of dissociation energy on ion formation and sensitivity of an analytical method for determination of chlorpyrifos in human blood using gas chromatography–mass spectrometer (GC–MS in MS/MS). Int J Mass Spectrom 253:48–57

    Article  CAS  Google Scholar 

  3. Hernández F, Sancho JV, Pozo OJ (2005) Critical review of the application of liquid chromatography/mass spectrometry to the determination of pesticide residues in biological samples. Anal Bioanal Chem 382:934–946

    Article  Google Scholar 

  4. Salm P, Taylor PJ, Roberts D, Silva JD (2009) Liquid chromatography–tandem mass spectrometry method for the simultaneous quantitative determination of the organophosphorus pesticides dimethoate, fenthion, diazinon and chlorpyrifos in human blood. J Chromatogr B 877:568–574

    Article  CAS  Google Scholar 

  5. Song ZH, Hou S, Zhang N (2002) A new green analytical procedure for monitoring sub-nanogram amounts of chlorpyrifos on fruits using flow injection chemiluminescence with immobilized reagents. J Agric Food Chem 50:4468–4474

    Article  CAS  Google Scholar 

  6. Li AF, Liu XY, Kong J, Huang R, Wu CM (2008) Chemiluminescence determination of organophosphorus pesticides chlorpyrifos in vegetable. Anal Lett 41:1375–1386

    Article  CAS  Google Scholar 

  7. Gámiz-Gracia L, García-Campana AM, Soto-Chinchilla JJ, Huertas-Pérez JF, González-Casado A (2005) Analysis of pesticides by chemiluminescence detection in the liquid phase. Trends Anal Chem 24:927–942

    Article  Google Scholar 

  8. Prabhakar N, Sumana G, Arora K, Singh H, Malhotra BD (2008) Improved electrochemical nucleic acid biosensor based on polyaniline-polyvinyl sulphonate. Electrochim Acta 53:4344–5350

    Article  CAS  Google Scholar 

  9. Simonian AL, Good TA, Wang SS, Wild JR (2005) Nanoparticle-based optical biosensors for the direct detection of organophosphate chemical warfare agents and pesticides. Anal Chim Acta 534:69–77

    Article  CAS  Google Scholar 

  10. Solanki PR, Prabhakar N, Pandey MK, Malhotra BD (2008) Self-assembled monolayer for toxicant detection using nucleic acid sensor based on surface plasmon resonance technique. Biomed Mircrodevies 10:757–767

    Article  CAS  Google Scholar 

  11. Viswanathan S, Radecka H, Radecki J (2009) Electrochemical biosensor for pesticides based on acetylcholinesterase immobilized on polyaniline deposited on vertically assembled carbon nanotubes wrapped with ssDNA. Biosens Bioelectron 24:2772–2777

    Article  CAS  Google Scholar 

  12. Zhao LX, Sun L, Chu XG (2009) Chemiluminescence immunoassay. Trends Anal Chem 28:404–415

    Article  CAS  Google Scholar 

  13. Knopp D (2006) Immunoassay development for environmental analysis. Anal Bioanal Chem 385:425–427

    Article  CAS  Google Scholar 

  14. Lin JM, Yamada M (2002) Chemiluminescence reaction of fluorescent organic compounds with KHSO5 using cobalt (II) as catalyst and its first application to molecular imprinting. Anal Chem 72:1148–1155

    Article  Google Scholar 

  15. He YH, Lu JR, Zhang HG, Du JX (2005) Molecular imprinting-chemiluminescence determination of norfloxacin using a norfloxacin-imprinted polymer as the recognition material. Microchim Acta 149:239–244

    Article  CAS  Google Scholar 

  16. Yang CY, Zhang ZJ, Chen SM, Yang F (2007) Molecularly imprinted on-line solid-phase extraction combined with chemiluminescence for the determination of pazufloxacin mesilate. Microchim Acta 159:299–304

    Article  CAS  Google Scholar 

  17. Lin JM, Yamada M (2000) Chemiluminescence reaction of fluorescent organic compounds with KHSO5 using cobalt (II) as catalyst and its first application to molecular imprinting. Anal Chem 72:1148–1155

    Article  CAS  Google Scholar 

  18. Surugiu I, Svitel J, Ye L, Haupt K, Danielsson B (2001) Development of a flow injection capillary chemiluminescent ELISA using an imprinted polymer instead of the antibody. Anal Chem 73:4388–4392

    Article  CAS  Google Scholar 

  19. Xie CG, Zhou HK, Gao S, Li HF (2010) Molecular imprinting method for on-line enrichment and chemiluminescence detection of the organophosphate pesticide triazophos. Microchim Acta 171:355–362

    Article  CAS  Google Scholar 

  20. Feng QZ, Zhao LX, Yan W, Ji F, Wei YL, Lin JM (2008) Molecularly imprinted solid-phase extraction and flow-injection chemiluminescence for trace analysis of 2,4-dichlorophenol in water samples. Anal Bioanal Chem 391:1073–1079

    Article  CAS  Google Scholar 

  21. Moreira FTC, Freitas VAP, Sales MGF (2011) Biomimetic norfloxacin sensors made of molecularly-imprinted materials for potentiometric transduction. Microchim Acta 172:15–23

    Article  CAS  Google Scholar 

  22. Xie CG, Liu BH, Wang ZY, Gao DM, Guan GJ, Zhang ZP (2008) Molecular imprinting at walls of silica nanotubes for TNT recognition. Anal Chem 80:437–443

    Article  CAS  Google Scholar 

  23. Xie CG, Zhang ZP, Wang DP, Guan GJ, Gao DM, Liu JH (2006) Surface molecular self-assembly strategy for TNT imprinting of polymer nanowire/nanotube arrays. Anal Chem 78:8339–8346

    Article  CAS  Google Scholar 

  24. Wang HF, He Y, Ji TR, Yan XP (2009) Surface molecular mmprinting on Mn-doped ZnS quantum dots for room-temperature phosphorescence optosensing of pentachlorophenol in Water. Anal Chem 81:1615–1621

    Article  CAS  Google Scholar 

  25. Xie CG, Li HF, Li SQ, Wu J, Zhang ZP (2010) Surface molecular self-assembly for organophosphate pesticide imprinting in electropolymerized poly(p-aminothiophenol) membranes on a gold nanoparticle modified glassy carbon electrode. Anal Chem 82:241–249

    Article  CAS  Google Scholar 

  26. Lu C, Zhou W, Han B, Yang H, Chen X, Wang X (2007) Surface-imprinted core-shell nanoparticles for sorbent assays. Anal Chem 79:5457–5461

    Article  CAS  Google Scholar 

  27. Gao DM, Zhang ZP, Wu MH, Xie CG, Guan GJ, Wang DP (2007) A surface functional monomer-directing strategy for highly dense imprinting of TNT at surface of silica nanoparticles. J Am Chem Soc 129:7859–7866

    Article  CAS  Google Scholar 

  28. Titirici MM, Sellergren B (2006) Thin molecularly imprinted polymer films via reversible addition-fragmentation chain transfer polymerization. Chem Mater 18:1773–1779

    Article  CAS  Google Scholar 

  29. Stöber W, Finker A, Bohn E (1968) Controlled growth of monodisperse silica spheres in the micron size range. J Colloid Interface Sci 26:62–69

    Article  Google Scholar 

  30. Philipse AP, Vrij AJ (1989) Preparation and properties of nonaqueous model dispersions of chemically modified, charged silica spheres. J Colloid Interface Sci 128:121–135

    Article  CAS  Google Scholar 

  31. Yilmaz E, Ramstrom O, Möller P, Sanchez D, Mosbach K (2002) A facile method preparing molecularly imprinted polymer spheres using spherical silica templates. J Mater Chem 12:1577–1581

    Article  CAS  Google Scholar 

  32. Surugiu I, Danielsson B, Ye L, Mosbach K, Haupt K (2001) Chemiluminscence imaging ELISA using an imprinted polymer as the recognition element instead of an antibody. Anal Chem 73:487–491

    Article  CAS  Google Scholar 

  33. Sabatani E, Gafni Y, Rubinstein I (1995) Morphology control in electrochemically grown conducting polymer films. 3. A comparative study of polyaniline films on bare gold pretreated with p-aminothiophenol. J Phys Chem 99:12305–12311

    Article  CAS  Google Scholar 

  34. Easton PM, Aimmonds AC, Rakishev A, Egorov AM, Candeias LP (1996) Quantitative model of the enhancement of peroxidase-induced luminol luminescence. J Am Chem Soc 118:6619–6624

    Article  CAS  Google Scholar 

  35. Diaz AN, Sanchez FG, Garcia JAG (1994) Nonlinear multicomponent kinetic analysis for the simultaneous stopped-flow determination of chemiluminescence enhancers. Anal Chem 66:988–993

    Article  Google Scholar 

  36. Wang JN, Zhang C, Wang HX, Yang FZ, Zhang XR (2001) Development of a luminol-based chemiluminescence flow-injection method for the determination of dichlorvos pesticide. Talanta 54:1185–1193

    Article  CAS  Google Scholar 

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Acknowledgments

This work was supported by the National Natural Science Foundation of the People’s Republic of China (No. 20875070).

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Authors and Affiliations

  1. Anhui Provincial Laboratory of Biomimetic Sensor and Detecting Technology, School of Materials and Chemical Engineering, West Anhui University, Lu’an, Anhui, 237012, People’s Republic of China

    Chenggen Xie, Huaifen Li, Shanqi Li & Shan Gao

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  1. Chenggen Xie
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  2. Huaifen Li
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  3. Shanqi Li
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  4. Shan Gao
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Correspondence to Chenggen Xie.

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Xie, C., Li, H., Li, S. et al. Surface molecular imprinting for chemiluminescence detection of the organophosphate pesticide chlorpyrifos. Microchim Acta 174, 311–320 (2011). https://doi.org/10.1007/s00604-011-0626-z

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  • DOI: https://doi.org/10.1007/s00604-011-0626-z

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