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Analytical and Bioanalytical Chemistry

, Volume 406, Issue 3, pp 831–839 | Cite as

Preparation of magnetic dummy molecularly imprinted polymers for selective extraction and analysis of salicylic acid in Actinidia chinensis

  • Qing-Ping You
  • Mi-Jun Peng
  • Yu-Ping Zhang
  • Jun-Fang Guo
  • Shu-Yun ShiEmail author
Research Paper

Abstract

Compounds with strong intramolecular hydrogen bonds (e.g., salicylic acid) have weak intermolecular hydrogen bonding interactions between them and functional monomers in the imprinting process. Consequently, the corresponding molecularly imprinted polymers (MIPs) have no specific adsorption ability. Here, the first magnetic dummy MIPs (MDMIPs) based on benzonic acid as dummy template are successfully developed and evaluated with respect to the applications in selective enrichment and analysis of salicylic acid from complex mixtures. Various parameters affecting absorption/desorption were evaluated for achieving optimal recovery and reducing nonspecific interactions. The prepared MDMIPs showed high adsorption capacity, good selectivity, rapid kinetic binding (40 min) and magnetic separation (5 s), high reproducibility (RSD< 4 % for batch-to-batch evaluation), and stability (only 4 % decrease after 6 cycles). Owing to the efficacy in specific binding and removal of interference, trace level salicylic acid was quantified (0.2 μg/g of fresh mass) in Actinidia chinensis by high-performance liquid chromatography.

Keywords

Molecularly imprinted polymers Magnetic separation Salicylic acid Actinidia chinensis 

Notes

Acknowledgments

This project was supported by the National Natural Science Foundation of China (21275163, 21005089), the Science and Technology Program of Hunan Province, China (2012FJ2006), the Postdoctoral Science Foundation of Central South University, the Shenghua Yuying project of Central South University, and aid program for Science and Technology Innovative Research Team (Chemicals of Forestry Resources and Development of Forest Products) in Higher Educational Institutions of Hunan Province.

References

  1. 1.
    Du QZ, Xu YJ, Li L, Zhao Y, Jerz G, Winterhalter P (2006) Antioxidant constituents in the fruits of Luffa cylindrica (L.) Roem. J Agric Food Chem 54:4186–4190CrossRefGoogle Scholar
  2. 2.
    González-Curbelo MA, Herrera-Herrera AV, Ravelo-Pérez LM, Hernández-Borges J (2013) Sample-preparation methods for pesticide-residue analysis in cereals and derivatives. Trends Anal Chem 38:32–51CrossRefGoogle Scholar
  3. 3.
    Martín-Esteban A (2013) Molecularly-imprinted polymers as a versatile, highly selective tool in sample preparation. Trends Anal Chem 45:169–181CrossRefGoogle Scholar
  4. 4.
    Maldim IM, Souza MCD, Souza JCJD, Figueiredo EC, Martins I (2012) Application of the molecularly imprinted solid-phase extraction to the organophosphate residues determination in strawberries. Anal Bioanal Chem 404:6–7Google Scholar
  5. 5.
    Zhan J, Fang GZ, Yan Z, Pan MF, Liu CC, Wang S (2013) Preparation of a semicovalent, molecularly surface imprinted polymer for the rapid determination of trace acid orange II in food and environmental samples. Anal Bioanal Chem 405:6353–6363CrossRefGoogle Scholar
  6. 6.
    Liu SS, Chen HM, Lu XH, Deng CH, Zhang XM, Yang PY (2010) Facile synthesis of copper(II) immobilized on magnetic mesoporous silica microspheres for selective enrichment of peptides for mass spectrometry analysis. Angew Chem Int Ed 49:7557–7561CrossRefGoogle Scholar
  7. 7.
    Madrakian T, Afkhami A, Mahmood-Kashani H, Ahmadi M (2013) Superparamagnetic surface molecularly imprinted nanoparticles for sensitive solid-phase extraction of tramadol from urine samples. Talanta 105:255–261CrossRefGoogle Scholar
  8. 8.
    Liu WF, Zhao HJ, Yang YZ, Liu XG, Xu BS (2013) Reactive carbon microspheres prepared by surface-grafting 4-(chloromethyl)phenyltrimethoxysilane for preparing molecularly imprinted polymer. Appl Surf Sci 277:146–154CrossRefGoogle Scholar
  9. 9.
    Yang WM, Liu LK, Zhou ZP, Liu H, Xie BZ, Xu WZ (2013) Rational preparation of dibenzothiophene-imprinted polymers by surface imprinting technique combined with atom transfer radical polymerization. Appl Surf Sci 282:809–819CrossRefGoogle Scholar
  10. 10.
    Xiao DL, Dramou P, Xiong NQ, He H, Yuan DH, Dai H, Li H, He XM, Peng J, Li N (2013) Preparation of molecularly imprinted polymers on the surface of magnetic carbon nanotubes with a pseudo template for rapid simultaneous extraction of four fluoroquinolones in egg samples. Analyst 138:3287–3296CrossRefGoogle Scholar
  11. 11.
    Shen XT, Zhu LH, Liu GX, Yu HW, Tang HQ (2008) Enhanced photocatalyticdegradation and selective removal of nitrophenols by using surface molecular imprinted titania. Environ Sci Technol 42:1687–1692CrossRefGoogle Scholar
  12. 12.
    Barahona F, Turiel E, Martín-Esteban A (2011) Molecularly imprinted polymer grafted to porous polyethylene frits: a new selective solid-phase extraction format. J Chromatogr A 1218:7065–7070CrossRefGoogle Scholar
  13. 13.
    Lin ZK, Cheng WJ, Li YY, Liu ZR, Chen XP, Huang CJ (2012) A novel superparamagnetic surface molecularly imprinted nanoparticle adopting dummy template: an efficient solid-phase extraction adsorbent for bisphenol A. Anal Chim Acta 720:71–76CrossRefGoogle Scholar
  14. 14.
    Yan HY, Cheng XL, Sun N (2013) Synthesis of multi-core–shell magnetic molecularly imprinted microspheres for rapid recognition of dicofol in tea. J Agric Food Chem 61:2896–2901CrossRefGoogle Scholar
  15. 15.
    Zhang TL, Liu F, Chen W, Wang J, Li KA (2001) Influence of intramolecular hydrogen bond of templates on molecular recognition of molecularly imprinted polymers. Anal Chim Acta 450:53–61CrossRefGoogle Scholar
  16. 16.
    Koeber R, Fleischer C, Lanza F, Boos KS, Sellergren B, Barceló D (2001) Evaluation of a multidimensional solid-phase extraction platform for highly selective on-line cleanup and high-throughput LC-MS analysis of triazines in river water samples using molecularly imprinted polymers. Anal Chem 73:2437–2444CrossRefGoogle Scholar
  17. 17.
    Matsui J, Fujiwara K, Takeuchi T (2000) Atrazine-selective polymers prepared by molecular imprinting of trialkylmelamines as dummy template species of atrazine. Anal Chem 72:1810–1813CrossRefGoogle Scholar
  18. 18.
    Matsui J, Fujiwara K, Ugata S, Takeuchi T (2000) Solid-phase extraction with a dibutylmelamine-imprinted polymer as triazine herbicide-selective sorbent. J Chromatogr A 889:25–31CrossRefGoogle Scholar
  19. 19.
    Quaglia M, Chenon K, Hall J, De Lorenzi E, Sellergren B (2001) Target analogue imprinted polymers with affinity for folic acid and related compounds. J Am Chem Soc 123:2146–2154Google Scholar
  20. 20.
    Rozhon W, Petutschnig E, Wrzaczek M, Jonak C (2005) Quantification of free and total salicylic acid in plants by solid-phase extraction and isocratic high-performance anion-exchange chromatography. Anal Bioanal Chem 382:1620–1627CrossRefGoogle Scholar
  21. 21.
    Klessig DF, Malamy J (1994) The salicylic acid signal in plants. Plant Mol Biol 26:1439–1458CrossRefGoogle Scholar
  22. 22.
    Raskin I (1992) Role of salicylic acid in plants. Plant Mol Biol 43:439–463Google Scholar
  23. 23.
    Liu LL, Shi SY, Chen XQ, Peng MJ (2013) Analysis of tyrosinase binders from Glycyrrhiza uralensis root: evaluation and comparison of tyrosinase immobilized magnetic fishing-HPLC and reverse ultrafiltration-HPLC. J Chromatogr B 932:19–25CrossRefGoogle Scholar
  24. 24.
    Yan F, Li J, Fu R, Lu Z, Yang WS (2009) Facile preparation of superparamagnetic Fe3O4/poly(St-co-MPS)/SiO2 composite particles with high magnetization by introduction of silanol groups. J Nanosci Nanotechnol 9:5874–5879CrossRefGoogle Scholar
  25. 25.
    Jing T, Du HR, Dai Q, Xia H, Niu JW, Hao QL, Mei SR, Zhou YK (2010) Magnetic molecularly imprinted nanoparticles for recognition of lysozyme. Biosens Bioelectron 26:301–306CrossRefGoogle Scholar
  26. 26.
    Kong X, Gao RX, He XW, Chen LX, Zhang YK (2012) Synthesis and characterization of the core–shell magnetic molecularly imprinted polymers (Fe3O4@MIPs) adsorbents for effective extraction and determination of sulfonamides in the poultry feed. J Chromatogr A 1245:8–16CrossRefGoogle Scholar
  27. 27.
    Zhang ZM, Tan W, Hu YL, Li GK (2011) Simultaneous determination of trace sterols in complicated biological samples by gas chromatography–mass spectrometry coupled with extraction using β-sitosterol magnetic molecularly imprinted polymer beads. J Chromatogr A 1218:4275–4283CrossRefGoogle Scholar
  28. 28.
    Chen FF, Xie XY, Shi YP (2013) Preparation of magnetic molecularly imprinted polymer for selective recognition of resveratrol in wine. J Chromatogr A 1300:112–118CrossRefGoogle Scholar
  29. 29.
    Park HJ, McConnell JT, Boddohi S, Kipper MJ, Johnson PA (2011) Synthesis and characterization of enzyme–magnetic nanoparticle complexes: effect of size on activity and recovery. Colloids Surf B 83:198–203CrossRefGoogle Scholar
  30. 30.
    Gao RX, Kong X, Wang X, He XW, Chen LX, Zhang YK (2011) Preparation and characterization of uniformly sized molecularly imprinted polymers functionalized with core–shell magnetic nanoparticles for the recognition and enrichment of protein. J Mater Chem 21:17863–17871CrossRefGoogle Scholar
  31. 31.
    Luo XB, Deng F, Luo SL, Tu XM, Yang LX (2011) Grafting of molecularly imprinted polymers from the surface of Fe3O4 nanoparticles containing double bond via suspension polymerization in aqueous environment: a selective sorbent for theophylline. J Appl Polym Sci 121:1930–1937CrossRefGoogle Scholar
  32. 32.
    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 78:8339–8346CrossRefGoogle Scholar
  33. 33.
    Yan HY, Liu ST, Gao MM, Sun N (2013) Ionic liquids modified dummy molecularly imprinted microspheres as solid phase extraction materials for the determination of clenbuterol and clorprenaline in urine. J Chromatogr A 1294:10–16CrossRefGoogle Scholar
  34. 34.
    Haupt K, Dzgoev A, Mosbach K (1998) Assay system for the herbicide 2,4-dichlorophenoxyacetic acid using a molecularly imprinted polymer as an artificial recognition element. Anal Chem 70:628–631CrossRefGoogle Scholar
  35. 35.
    Chen LX, Xu SF, Li JH (2011) Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. Chem Soc Res 40:2922–2942CrossRefGoogle Scholar
  36. 36.
    Yuan Y, Wang YZ, Huang MD, Xu R, Zeng H, Nie C, Kong JH (2011) Development and characterization of molecularly imprinted polymers for the selective enrichment of podophyllotoxin from traditional Chinese medicines. Anal Chim Acta 695:63–72CrossRefGoogle Scholar
  37. 37.
    Zhang MS, Huang JR, Yu P, Chen X (2010) Preparation and characteristics of protein molecularly imprinted membranes on the surface of multiwalled carbon nanotubes. Talanta 81:162–166CrossRefGoogle Scholar
  38. 38.
    Chen FF, Xie XY, Shi YP (2012) Magnetic molecularly imprinted polymer for the detection of rhaponticin in Chinese patent medicines. J Chromatogr A 1252:8–14CrossRefGoogle Scholar
  39. 39.
    Zhang H, Dramou P, He H, Tan SH, Pham-Huy C, Pan HJ (2012) Molecularly imprinted stationary phase prepared by reverse micro-emulsion polymerization for selective recognition of gatifloxacin in aqueous media. J Chromatogr Sci 50:499–508CrossRefGoogle Scholar
  40. 40.
    Peng L, Wang YZ, Zeng H, Yuan Y (2011) Molecularly imprinted polymer for solid-phase extraction of rutin in complicated traditional Chinese medicines. Analyst 136:756–763CrossRefGoogle Scholar
  41. 41.
    Hayat Q, Hayat S, Irfan M, Ahmad A (2010) Effect of exogenous salicylic acid under changing environment: a review. Environ Exp Bot 68:14–25CrossRefGoogle Scholar
  42. 42.
    Zhang Y, Chen KS, Zhang SL (2004) Extraction and determination of endogenous salicylic acid from kiwifruit and its application to postharvest research. J Chin Inst Food Sci Technol 4:6–9Google Scholar
  43. 43.
    Montefiori M, McGhie TK, Costa G, Ferguson AR (2005) Pigments in the fruit of red-fleshed kiwifruit (Actinidia chinensis and Actinidia deliciosa). J Agric Food Chem 53:9526–9530CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  • Qing-Ping You
    • 1
  • Mi-Jun Peng
    • 1
    • 2
  • Yu-Ping Zhang
    • 1
  • Jun-Fang Guo
    • 1
  • Shu-Yun Shi
    • 1
    • 3
    Email author
  1. 1.School of Chemistry and Chemical EngineeringCentral South UniversityChangshaChina
  2. 2.Key Laboratory of Hunan Forest Products and Chemical Industry EngineeringJishou UniversityZhangjiajieChina
  3. 3.Key Laboratory of Resources Chemistry of Nonferrous MetalsCentral South UniversityChangshaChina

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