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Preparation and characterization of novel thermosensitive magnetic molecularly imprinted polymers for selective recognition of norfloxacin

  • Weihong Huang
  • Yu Kong
  • Wenming Yang
  • Xiaoni Ni
  • Ningwei Wang
  • Yi Lu
  • Wanzhen Xu
Article

Abstract

Novel norfloxacin (NOR) thermosensitive magnetic molecularly imprinted polymers (T-MMIPs) were prepared with functional monomer methacrylic acid (MAA), temperature-response monomer N-isopropylacrylamide (NIPAM) and cross-linking agent N,N′-methylenebisacrylamide (MBA) by the surface imprinting technique. The silica layer and imprinted polymers layer coated on the surface of Fe3O4 nanoparticles, forming double-shell structure. The morphology and composition of the thermosensitive magnetic molecularly imprinted polymers were investigated by transmission electronmicroscope (TEM), Fourier transform infrared spectrometry (FT-IR), thermogravimetic (TGA), vibrating sample magnetometer (VSM), powder X-ray diffraction (XRD) and nitrogen adsorption analysis. The phase behavior and thermosensitivity of T-MMIPs were studied by swelling experiments and adsorption tests at different temperatures. And the adsorption performance of T-MMIPs at 35 °C were evaluated by adsorption experiments, including kinetic, isotherm and selectivity tests. The maximum capacity of T-MMIPs at 35 °C was 52.85 mg g−1. In selective recognition tests, the T-MMIPs showed the highest selectivity for NOR among four components while the T-MNIPs showed similarly adsorption for all components. The prepared T-MMIPs have great potential in the detection and separation of norfloxacin due to the good temperature response, adsorption capacity, selectivity and reusability.

Keywords

Molecularly imprinted polymers Norfloxacin Thermosensitive Selective 

Notes

Acknowledgments

This work was supported by the Jiangsu Natural Science Foundation of China (contract grant numbers BK20141287, BK20151323 and BK20151337), Postdoctoral Science Foundation of China (contract grant numbers 2014 M560405 and 2015 T80515), Postdoctoral Science Foundation of Jiangsu Province (contract grant number 1401012 A), Jiangsu Collaborative Innovation Center of Technology and Material of Water Treatment, Social Development Fund of Jiangsu Province (contract grant number SH2014020).

References

  1. 1.
    Martinez M, McDermott P, Walker R (2006) Pharmacology of the fluoroquinolones: A perspective for the use in domestic animals. Vet J 172:10–28CrossRefGoogle Scholar
  2. 2.
    Appelbaum PC, Hunter PA (2000) The fluoroquinolone antibacterials: past, present and future perspectives. Int J Antimicrob Agents 16:5–15CrossRefGoogle Scholar
  3. 3.
    Batt AL, Bruce IB, Aga DS (2006) Evaluating the vulnerability of surface waters to antibiotic contamination from varying wastewater treatment plant discharges. Environ Pollut 142:295–302CrossRefGoogle Scholar
  4. 4.
    Gulkowska A, Leung HW, So MK, et al. (2008) Removal of antibiotics from wastewater by sewage treatment facilities in Hong Kong and Shenzhen. China, Water Res 42:395–403CrossRefGoogle Scholar
  5. 5.
    Pedersen K, Wedderkopp A (2003) Resistance to quinolones in campylobacter jejuni and campylobacter coli from Danish broilers at farm level. J Appl Microbiol 94:111–119CrossRefGoogle Scholar
  6. 6.
    Carlucci G (1998) Analysis of fluoroquinolones in biological fluids by high-performance liquid chromatography. J Chromatogr A 812:343–367CrossRefGoogle Scholar
  7. 7.
    Andreu V, Blasco C, Picó Y (2007) Analytical strategies to determine quinolone residues in food and the environment. Trac-Trends Anal Chem 26:534–556CrossRefGoogle Scholar
  8. 8.
    Phan TPH, Managaki S, Nakada N, et al. (2011) Antibiotic contamination and occurrence of antibiotic-resistant bacteria in aquatic environments of Northern Vietnam. Sci Total Environ 409:2894–2901CrossRefGoogle Scholar
  9. 9.
    Oberlé K, Capdeville MJ, Berthe T, Budzinski H, Petit F (2012) Evidence for a complex relationship between antibiotics and antibiotic-resistant Escherichia coli: from medical center patients to a receiving environment. Environ Sci Technol 46:1859–1868CrossRefGoogle Scholar
  10. 10.
    Boree AL, Arnold WA, McNeil K (2004) Photochemical fate of sulfa drugs in the aquatic environment: sulfa drugs containing five-membered heterocycylic groups. Environ Sci Technol 38:3933–3940CrossRefGoogle Scholar
  11. 11.
    Hoshino Y, Koide H, Urakami T, et al. (2010) Recognition, neutralization, and clearance of Target peptides in the bloodstream of living mice by molecularly imprinted polymer nanoparticles: A plastic antibody. J Am Chem Soc 132:6644–6645CrossRefGoogle Scholar
  12. 12.
    Wulff G (2002) Enzyme-like catalysis by molecularly imprinted polymers. Chem Rev 102:1–27CrossRefGoogle Scholar
  13. 13.
    Zimmerman SC, Lemcoff NG, Synthetic hosts via molecular imprinting—are universal synthetic antibodies realistically possible. Chem Commun 1:5–14Google Scholar
  14. 14.
    Cheong WJ, Yang SH, Ali F (2013) Molecular imprinted polymers for separation science: A review of reviews. J Sep Sci 36:609–628CrossRefGoogle Scholar
  15. 15.
    Lasaková M, Jandera P (2009) Molecularly imprinted polymers and their application in solid phase extraction. J Sep Sci 32:799–812CrossRefGoogle Scholar
  16. 16.
    Trojanowicz M (2014) Enantioselective electrochemical sensors and biosensors: a mini-review. Electrochem Commun 38:47–52CrossRefGoogle Scholar
  17. 17.
    Turiel E, Martín-Esteban A (2010) Molecularly imprinted polymers for sample preparation: a review. Anal Chim Acta 668:87–99CrossRefGoogle Scholar
  18. 18.
    Martín-Esteban A (2013) Molecularly-imprinted polymers as a versatile, highly selective tool in sample preparation. TrAC Trends Anal Chem 45:169–181CrossRefGoogle Scholar
  19. 19.
    Zhu R, Zhao W, Zhai M, et al. (2010) Molecularly imprinted layer-coated silica nanoparticles for selective solid-phase extraction of bisphenol A from chemical cleansing and cosmetics samples. Anal Chim Acta 658:209–216CrossRefGoogle Scholar
  20. 20.
    Li H, Li G, Li ZP, et al. (2013) Surface imprinting on nano-TiO2 as sacrificial material for the preparation of hollow chlorogenic acid imprinted polymer and its recognition behavior. Appl Surf Sci 264:644–652CrossRefGoogle Scholar
  21. 21.
    Zhang M, Huang J, 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
  22. 22.
    Hua ZD, Zhou S, Zhao MP (2009) Fabrication of a surface imprinted hydrogel shell over silica microspheres using bovine serum albumin as a model protein template. Biosens Bioelectron 25:615–622CrossRefGoogle Scholar
  23. 23.
    Zhou WH, Lu CH, Guo XC, et al. (2010) Mussel-inspired molecularly imprinted polymer coating superparamagnetic nanoparticles for protein recognition. J Mater Chem 20:880–883CrossRefGoogle Scholar
  24. 24.
    Ma ML, Zhang QY, Dou JB, et al. (2012) Fabrication of one-dimensional Fe3O4/P(GMA–DVB) nanochains by magnetic-field-induced precipitation polymerization. J Colloid Interface Sci 374:339–344CrossRefGoogle Scholar
  25. 25.
    Lu Y, Yin Y, Mayers BT, Xia Y (2002) Modifying the surface properties of superparamagnetic iron oxide nanoparticles through a sol-gel approach. Nano Lett 2:183–186CrossRefGoogle Scholar
  26. 26.
    Yang D, Hu JH, Fu SK (2009) Controlled synthesis of magnetite − silica nanocomposites via a Seeded Sol − gel approach. J Phys Chem C 113:7646–7651CrossRefGoogle Scholar
  27. 27.
    Li LF, Chen L, Liu WF, Yang YZ, Liu XG, Chen YK (2015) Preparation and characterization of 5-fluorouracil surface-imprinted thermosensitive magnetic microspheres. J Polym Res 146:441–447Google Scholar
  28. 28.
    Holtz JH, Asher SA (1997) Polymerized colloidal crystal hydrogel films as intelligent chemical sensing materials. Nature 389:829–831CrossRefGoogle Scholar
  29. 29.
    Smithe DW, Kang MS, Gupta VK (2001) Telechelic poly (N-isopropylacrylamide): polymerization and chain aggregation in solution. Macromolecules 3:8503–8511CrossRefGoogle Scholar
  30. 30.
    Torres-Lugo M, Peppas NA (1999) Molecular design and in vitro studies of novel pH-sensitive hydrogels for the oral delivery of calcitonin. Macromolecules 32:6646–6651CrossRefGoogle Scholar
  31. 31.
    Sun X, Zhao CY, Wang XH, Huang YP, Liu ZS (2014) Thermoresponsive ketoprofen-imprinted monolith prepared in ionic liquid. J Polym Res 406:5359–5367Google Scholar
  32. 32.
    Wang HW, Liu YQ, Wei SL, Yao S, Zhang JL, Huang HC (2016) Selective extraction and determination of fluoroquinolones in bovine milk samples with montmorillonite magnetic molecularly imprinted polymers and capillary electrophoresis. J Polym Res 408:589–598Google Scholar
  33. 33.
    Schild HG (1992) Poly (N-isopropylacrylamide): experiment, theory and application. Prog Polym Sci 17:163–249CrossRefGoogle Scholar
  34. 34.
    Fang LJ, Fang SJ, Guo XZ, et al. (2012) Azobenzene-containing molecularly imprinted polymer microspheres with photo- and thermoresponsive template binding properties in Pure Aqueous Media by atom transfer radical polymerization. Langmuir 28:9767–9777CrossRefGoogle Scholar
  35. 35.
    Li SJ, Li S, Gong SQ (2009) Modulated molecular recognition by a temperature-sensitive molecularly- imprinted polymer. J Polym Sci Part A: Polym Chem 47:2352–2360CrossRefGoogle Scholar
  36. 36.
    Pan GQ, Zhang Y, Guo XZ, et al. (2010) An efficient approach to obtaining water-compatible and stimuli-responsive molecularly imprinted polymers by the facile surface-grafting of functional polymer brushes via RAFT polymerization. Biosens Bioelectron 26:976–982CrossRefGoogle Scholar
  37. 37.
    Turiel E, Martin-Esteban A, Tadeo JL (2007) Molecular imprinting-based separation methods for selective analysis of fluoroquinolones in soils. J Chromatogr A 1172:97–104CrossRefGoogle Scholar
  38. 38.
    Wang JP, Pan MF, Fang GZ, Wang S (2009) Preparation of a novel molecularly imprinted polymer by a sol-gel process for on-line solid-phase extraction coupled with high performance liquid chromatography to detect trace enrofloxacin in fish and chicken samples. Microchim Acta 166:295–302CrossRefGoogle Scholar
  39. 39.
    Zhang D, Lv YK, Chen R, Shi CC (2013) Preparation and evaluation of a molecularly imprinted Sol-Gel Hybrid material for selective solid-phase extraction of sarafloxacin in milk. Asian J Chem 25:3922–3926Google Scholar
  40. 40.
    Lv YK, Wang LM, Yang L, et al. (2012) Synthesis and application of molecularly imprinted poly(methacrylic acid)–silica hybrid composite material for selective solid-phase extraction and high-performance liquid chromatography determination of oxytetracycline residues in milk. J Chromatogr A 1227:48–53CrossRefGoogle Scholar
  41. 41.
    Deng H, Li X, Peng Q, et al. (2005) Monodisperse magnetic single-Crystal Ferrite Microspheres. Angew Chem Int Ed 44:2782–2785CrossRefGoogle Scholar
  42. 42.
    Stöber W, Fink A, Bohn E (1968) Controlled growth of monodisperse silica spheres in the micron size range. J Colloid Interface Sci 26:62–69CrossRefGoogle Scholar
  43. 43.
    Jing T, Du HR, Dai Q, et al. (2010) Magnetic molecularly imprinted nanoparticles for recognition of lysozyme. Biosens Bioelectron 26:301–306CrossRefGoogle Scholar
  44. 44.
    Ma PF, Zhou ZP, Yang WM, et al. (2015) Preparation and application of sulfadiazine surface molecularly imprinted polymers with temperature-responsive properties. J Appl Polym Sci 132:41769–41770Google Scholar
  45. 45.
    Zhang BL, Zhang HP, Fan XL, et al. (2013) Preparation of thermoresponsive Fe3O4/P(acrylic acid–methyl methacrylate–N-isopropylacrylamide) magnetic composite microspheres with controlled shell thickness and its releasing property for phenolphthalein. J Colloid Interf Sci 398:51–58CrossRefGoogle Scholar
  46. 46.
    Lagergren S, Sven K (1898) Vetenskapsakad. Zur Theorie Der Sogenannten Adsorption Geloster Stoffe Handl 24:1–39Google Scholar
  47. 47.
    Ho YS, Mckay G (1999) Pseudo-second order model for sorption processes. Process Biochem 34:451–465CrossRefGoogle Scholar
  48. 48.
    Baydenmir G, Andac M, Bereli N, Say R, Denizli A (2007) Selective removal ofbilirubin from human plasma with bilirubin-imprinted particles. Ind Eng Chem Res 46:2843–2852CrossRefGoogle Scholar
  49. 49.
    Cao Y, Liu LK, Xu WZ, et al. (2013) Surface molecularly imprinted polymer prepared by reverse atom transfer radical polymerization for selective adsorption indole. J Appl Polym Sci 131:40473–40474Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2016

Authors and Affiliations

  • Weihong Huang
    • 1
  • Yu Kong
    • 1
  • Wenming Yang
    • 2
  • Xiaoni Ni
    • 3
  • Ningwei Wang
    • 4
  • Yi Lu
    • 4
  • Wanzhen Xu
    • 1
  1. 1.School of Environment and Safety EngineeringJiangsu UniversityZhenjiangChina
  2. 2.School of Materials Science and EngineeringJiangsu UniversityZhenjiangChina
  3. 3.Zhenjiang Institute for Drug Control of Jiangsu ProvinceZhenjiangChina
  4. 4.Zhenjiang Entry-Exit Inspection Quarantine BureauZhenjiangPeople’s Republic of China

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