Abstract
In this work, super-paramagnetic interface molecularly imprinted microspheres (MIMIMs) were prepared using an immunostimulating hexapeptide as template via photo-initiated Pickering emulsion polymerization by the self-assembly of the template-immobilized silica nanoparticles at the oil–water interface under room temperature. The whole experiment process was tracked and analyzed by various characterization methods. Results manifest that the obtained MIMIMs showed excellent recognition property and rapid-efficiency separation for template peptide due to their accessible imprinted sites and desired magnetic susceptibility. Moreover, MIMIMs were used in competitive rebinding and reusability tests, which demonstrated their potential application in the enrichment of IHH and sustainable performance in resource-saving.
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Whitcombe M, Chianella I, Larcombe L, Piletsky S, Noble J, Porter R, Horgan A (2011) The rational development of molecularly imprinted polymer-based sensors for protein detection. Chem Soc Rev 40:1547–1571
De Strooper B, Vassar R, Golde T (2010) The secretases: enzymes with therapeutic potential in Alzheimer disease. Nat Rev Neurol 6:99–107
Erdmann K, Cheung B, Schröder H (2008) The possible roles of food-derived bioactive peptides in reducing the risk of cardiovascular disease. J Nutr Biochem 19:643–654
Jaziri M, Migliore-Samour D, Casabianca-Pignède M, Keddad K, Morgat J, Jollès P (1992) Specific binding sites on human phagocytic blood cells for Gly–Leu–Phe and Val–Glu–Pro–Ile–Pro–Tyr, immunostimulating peptides from human milk proteins. BBA-Protein Struct Mol Enzymol 1160:251–261
Sharma P, Singh N, Garg R, Haq W, Dube A (2004) Efficacy of human β-casein fragment (54–59) and its synthetic analogue compound 89/215 against Leishmania donovani in hamsters. Peptides 25:1873–188111
Thakur D, Saxena R, Singh V, Haq W, Katti S, Singh B, Tripathi R (2012) Human beta casein fragment (54–59) modulates M. bovis BCG survival and basic transcription factor 3 (BTF3) expression in THP-1 cell line. PLoS ONE 7:e45905
Gattegno L, Migliore-Samour D, Saffar L, Jolles P (1988) Enhancement of phagocytic activity of human monocytic-macrophagic cells by immunostimulating peptides from human casein. Immunol Lett 18:27–31
Brantl V, Teschemacher H, Henschen A, Lottspeich F (1979) Novel opioid peptides derived from casein (β-casomorphins) I Isolation from bovine casein peptone. Hoppe–Seyler´s Z Physiol Chem 360:1211–1224
Wulff G, Sarhan A (1972) Use of polymers with enzyme-analogous structures for resolution of racemates. Angew Chem Int Ed 11:341–345
Arshady R, Mosbach K (1981) Synthesis of substrate-selective polymers by host-guest polymerization. Die Makromol Chem 182:687–692
Whitcombe M, Rodriguez M, Villar P, Vulfson E (1995) A new method for the introduction of recognition site functionality into polymers prepared by molecular imprinting: synthesis and characterization of polymeric receptors for cholesterol. J Am ChemSoc 117:7105–7111
Whitcombe M, Kirsch N, Nicholls I (2014) Molecular imprinting science and technology: a survey of the literature for the years 2004–2011. J Mol Recognit 6:297–401
Hu J, Mao X, Cao S, Yuan X (2010) Recognition of proteins and peptides: rational development of molecular imprinting technology. Polym Sci Ser A 52:328–339
Du C, Hu X, Guan P, Guo L, Qian L, Li J, Song R, Tang Y (2015) Synthesis of water-compatible surface-imprinted composite microspheres with core–shell structure for selective recognition of thymopentin from aqueous solution. J Mater Sci 50:427–438. doi:10.1007/s10853-014-8602-8
Guo L, Hu X, Guan P, Du C, Wang D, Song D, Song R (2015) Facile preparation of superparamagnetic surface-imprinted microspheres using amino acid as template for specific capture of thymopentin. Appl Surf Sci 357:1490–1498
Wang Y, Li D, He X, Li W, Zhang Y (2015) Epitope imprinted polymer nanoparticles containing fluorescent quantum dots for specific recognition of human serum albumin. Microchim Acta 182:1465–1472
Schrade A, Landfester K, Ziener U (2013) Pickering-type stabilized nanoparticles by heterophase polymerization. Chem Soc Rev 42:6823–6839
Shen X, Ye L (2011) Interfacial molecular imprinting in nanoparticle-stabilized emulsions. Macromolecules 44:5631–5637
Shen X, Svensson Bonde J, Kamra T, Bülow L, Leo J, Linke D, Ye L (2014) Bacterial imprinting at Pickering emulsion interfaces. Angew Chem Int Ed 53:10687–10690
Zhou T, Zhang K, Kamra T, Bülow L, Ye L (2015) Preparation of protein imprinted polymer beads by Pickering emulsion polymerization. J Mater Chem B 3:1254–1260
Ramos J, Forcada J (2011) Surfactant-free miniemulsion polymerization as a simple synthetic route to a successful encapsulation of magnetite nanoparticles. Langmuir 27:7222–7230
Yang S, Zhang X, Zhao W, Sun L, Luo A (2015) Preparation and evaluation of Fe3O4 nanoparticles incorporated molecularly imprinted polymers for protein separation. J Mater Sci 51:937–949. doi:10.1007/s10853-015-9423-0
You Q, Peng M, Zhang Y, Guo J, Shi S (2014) Preparation of magnetic dummy molecularly imprinted polymers for selective extraction and analysis of salicylic acid in actinidia chinensis. Anal Bioanal Chem 406:831–839
Huang H, Wang X, Ge H, Xu M (2016) Multifunctional magnetic cellulose surface-imprinted microspheres for highly selective adsorption of artesunate. ACS Sustain Chem Eng 4:3334–3343
Yuet K, Hwang D, Haghgooie R, Doyle P (2009) Multifunctional superparamagnetic Janus particles. Langmuir 26:4281–4287
Lattuada M, Hatton T (2007) Preparation and controlled self-assembly of Janus magnetic nanoparticles. J Am Chem Soc 129:12878–12889
Chen K, Zhu Y, Zhang Y, Li L, Lu Y, Guo X (2011) Synthesis of magnetic spherical polyelectrolyte brushes. Macromolecules 44:632–639
Chakraborty S, Jähnichen K, Komber H, Basfar A, Voit B (2014) Synthesis of magnetic polystyrene nanoparticles using amphiphilic ionic liquid stabilized RAFT mediated miniemulsion polymerization. Macromolecules 47:4186–4198
Vashist S, Lam E, Hrapovic S, Male K, Luong J (2014) Immobilization of antibodies and enzymes on 3-aminopropyltriethoxysilane-functionalized bioanalytical platforms for biosensors and diagnostics. Chem Rev 114:11083–11130
Tan C, Chua H, Ker K, Tong Y (2008) Preparation of bovine serum albumin surface-imprinted submicrometer particles with magnetic susceptibility through core-shell miniemulsion polymerization. Anal Chem 80:683–692
Stöber W, Fink A, Bohn E (1968) Controlled growth of monodisperse silica spheres in the micron size range. J Colloid Interface Sci 26:62–69
Du C, Hu X, Guan P, Gao X, Song R, Li J, Guo L (2016) Preparation of surface-imprinted microspheres effectively controlled by orientated template immobilization using highly cross-linked raspberry-like microspheres for the selective recognition of an immunostimulating peptide. J Mater Chem B 4:1510–1519
Böhmler J, Ploux L, Ball V, Anselme K, Ponche A (2011) Necessity of a thorough characterization of functionalized silicon wafers before biointerface studies. J Phys Chem C 115:11102–11111
Libertino S, Giannazzo F, Aiello V, Scandurra A, Sinatra F, Renis M, Fichera M (2008) XPS and AFM characterization of the enzyme glucose oxidase immobilized on SiO2 surfaces. Langmuir 24:1965–1972
Iwahashi T, Nishi T, Yamane H, Miyamae T, Kanai K, Seki K, Ouchi Y (2009) Surface structural study on ionic liquids using metastable atom electron spectroscopy. J Phys Chem C 113:19237–19243
Du C, Hu X, Guan P, Guo L, Qian L, Song R, Wang C (2015) Water-compatible surface-imprinted microspheres for high adsorption and selective recognition of peptide drug from aqueous media. J Mater Chem B 3:3044–3053
Moulder J, Stickle W, Sobol P, Bomben K (1992) Handbook of X-ray photoelectron spectroscopy ed J Chastain (Eden Prairie, MN: Perkin-Elmer Corporation) chap. 2, pp 42–43
Cottenye N, Teixeira F, Ponche A, Reiter G, Anselme K, Meier W, Ploux L, Vebert-Nardin C (2008) Oligonucleotide nanostructured surfaces: effect on Escherichia coli curli expression. Macromol Biosci 8:1161–1172
Lofgreen J, Ozin G (2014) Controlling morphology and porosity to improve performance of molecularly imprinted sol–gel silica. Chem Soc Rev 43:911–933
Yu C, Mosbach K (1997) Molecular imprinting utilizing an amide functional group for hydrogen bonding leading to highly efficient polymers. J Org Chem 62:4057–4064
Yoshimatsu K, LeJeune J, Spivak D, Ye L (2009) Peptide-imprinted polymer microspheres prepared by precipitation polymerization using a single bi-functional monomer. Analyst 134:719–724
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The authors are grateful for the financial support provided by the National Natural Science Foundation of China (Grant No. 51433008), and the Graduate Starting Seed Fund of Northwestern Polytechnical University (Grant No. Z2016034).
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Zhang, X., Hu, X., Guan, P. et al. Immunostimulating peptide interfacial imprinted magnetic microspheres synthesized via Pickering emulsion polymerization. J Mater Sci 52, 4713–4726 (2017). https://doi.org/10.1007/s10853-016-0714-x
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DOI: https://doi.org/10.1007/s10853-016-0714-x