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Temperature-sensitive molecularly imprinted microgels with esterase activity

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Abstract

Temperature-sensitive molecularly imprinted microgels (MIGs) exhibiting esterase activity were prepared by a reverse emulsion method using dialdehyde dextran-histidine conjugate (PAD-His) as the functional macromonomer and p-nitrophenyl phosphate (NPP) as the stable transition state analogue (TSA) as well as Co2+ as the coordination center. The catalytic activity of MIGs was greatly influenced by the amount of the template, and could be modulated by temperature. The hydrolysis kinetics of p-nitrophenyl acetate (NPA) in the presence of MIGs could be described by the Michaelis-Menten equation. The Michaelis-Menten constant and maximum velocity were found to be 2.2 × 10−5 mol/L and 2.04 × 10∞8 mol/h, respectively. In addition, the MIGs were found to have a high catalytic selectivity to NPA.

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References

  1. Carboni D, Flavin K, Servant A, Gouverneur V, Resmini M. The first example of molecularly imprinted nanogels with aldolase type I activity. Chem Eur J, 2008, 14: 7059–7065

    CAS  Google Scholar 

  2. Becker JJ, Gagne MR. Exploiting the synergy between coordination chemistry and molecular imprinting in the quest for new catalysts. Acc Chem Res, 2004, 37: 798–804

    Article  CAS  Google Scholar 

  3. Lettau K, Warsinke A, Laschewsky A, Mosbach K, Yilmaz E, Scheller FW. An esterolytic imprinted polymer prepared via a silica-supported transition state analogue. Chem Mater, 2004, 16: 2745–2749

    Article  CAS  Google Scholar 

  4. Sellergren B, Karmalkar RN, Shea KJ. Enantioselective ester hydrolysis catalyzed by imprinted polymers. J Org Chem, 2000, 65: 4009–4027

    Article  CAS  Google Scholar 

  5. Matsui J, Nicholls IA, Karube I, Mosbach K. Carbon-carbon bond formation using substrate selective catalytic polymers prepared by molecular imprinting: an artificial class II aldolase. J Org Chem, 1996, 61: 5414–5417

    Article  CAS  Google Scholar 

  6. Cheng ZY, Zhang LW, Li YZ. Synthesis of an enzyme-like imprinted polymer with the substrate as the template, and its catalytic properties under aqueous conditions. Chem Eur J, 2004, 10: 3555–3561

    Article  CAS  Google Scholar 

  7. Tada M, Sasaki T, Iwasawa Y. Design of a novel molecular-imprinted Rh-amine complex on SiO2 and its shape-selective catalysis for α-methylstyrene hydrogenation. J Phys Chem B, 2004, 108: 2918–2930

    Article  CAS  Google Scholar 

  8. Liu JQ, Wulff G. Functional mimicry of carboxypeptidase A by a combination of transition state stabilization and a defined orientation of catalytic moieties in molecularly imprinted polymers. J Am Chem Soc, 2008, 130: 8044–8054

    Article  CAS  Google Scholar 

  9. Shechter I, Ramon O, Portnaya I, Paz Y, Livney YD. Microcalorimetric study of the effects of a chaotropic salt, KSCN, on the lower critical solution temperature (LCST) of aqueous poly (N-isopropy-lacrylamide) (PNIPA) solutions. Macromolecules, 2009, 43: 480–487

    Article  CAS  Google Scholar 

  10. Puoci F, Iemma F, Picci N. Stimuli-responsive molecularly imprinted polymers for drug delivery: a review. Curr Drug Deliver, 2008, 5: 85–96

    Article  CAS  Google Scholar 

  11. Huynh DP, Nguyen MK, Kim BS, Lee DS. Molecular design of novel pH/temperature-sensitive hydrogels. Polymer, 2009, 50: 2565–2571

    Article  CAS  Google Scholar 

  12. Lee Y, Chung HJ, Yeo S, Ahn CH, Lee H, Messersmith PB, Park TG. Thermo-sensitive, injectable, and tissue adhesive sol-gel transition hyaluronic acid/pluronic composite hydrogels prepared from bio-inspired catechol-thiol reaction. Soft Matter, 2010, 6: 977–983

    Article  CAS  Google Scholar 

  13. Park TG. Stabilization of enzyme immobilized in temperature-sensitive hydrogels. Biotechnol Lett, 1993, 15: 57–60

    Article  CAS  Google Scholar 

  14. Alexander C, Davidson L, Hayes W. Imprinted polymers: artificial molecular recognition materials with applications in synthesis and catalysis. Tetrahedron, 2003, 59: 2025–2057

    Article  CAS  Google Scholar 

  15. Anderson CD, Shea KJ, Rychnovsky SD. Strategies for the generation of molecularly imprinted polymeric nitroxide catalysts. Org Lett, 2005, 7: 4879–4882

    Article  CAS  Google Scholar 

  16. Volkmann A, Bruggemann O. Catalysis of an ester hydrolysis applying molecularly imprinted polymer shells based on an immobilized chiral template. Reac & Funct Polym, 2006, 66: 1725–1733

    Article  CAS  Google Scholar 

  17. Visnjevski A, Schomacker R, Yilmaz E, Bruggemann O. Catalysis of a Diels-Alder cycloaddition with differently fabricated molecularly imprinted polymers. Catal Commun, 2005, 6: 601–606

    Article  CAS  Google Scholar 

  18. Cheng ZY, Li YZ. The role of molecular recognition in regulating the catalytic activity of peroxidase-like polymers imprinted by a reductant substrate. J Mol Catal A: Chem, 2006, 256: 9–15

    Article  CAS  Google Scholar 

  19. Svenson J, Zheng N, Nicholls IA. A molecularly imprinted polymer-based synthetic transaminase. J Am Chem Soc, 2004, 126: 8554–8560

    Article  CAS  Google Scholar 

  20. Stewart JD, Liotta LJ, Benkovic SJ. Reaction mechanisms displayed by catalytic antibodies. Acc Chem Res, 1993, 26: 396–404

    Article  CAS  Google Scholar 

  21. Tong KJ, Xiao S, Li SJ, Wang J. Molecular recognition and catalysis by molecularly imprinted polymer catalysts: thermodynamic and kinetic surveys on the specific behaviors. J Inorg Organomet Polym, 2008, 18: 426–433

    Article  CAS  Google Scholar 

  22. Kawanami Y, Yunoki T, Nakamura A, Fujii K, Umano K, Yamauchi H, Masuda K. Imprinted polymer catalysts for the hydrolysis of p-nitrophenyl acetate. J Mol Catal A: Chem, 1999, 145: 107–110

    Article  CAS  Google Scholar 

  23. Agarwal A, Gupta U, Asthana A, Jain NK. Dextran conjugated dendritic nanoconstructs as potential vectors for anti-cancer agent. Biomaterials, 2009, 30: 3588–3596

    Article  CAS  Google Scholar 

  24. Bruneel D, Schacht E. Chemical modification of pullulan: 1. Periodate oxidation. Polymer, 1993, 34: 2628–2632

    CAS  Google Scholar 

  25. Cheung RY, Ying YM, Rauth AM, Marcon N, Wu XY. Biodegradable dextran-based microspheres for delivery of anticancer drug mitomycin C. Biomaterials, 2005, 26: 5375–5385

    Article  CAS  Google Scholar 

  26. Brunel F, Veron L, David L, Domard A, Delair T. A novel synthesis of chitosan nanoparticles in reverse emulsion. Langmuir, 2008, 24: 11370–11377

    Article  CAS  Google Scholar 

  27. Emgenbroich M, Wulff G. A new enzyme model for enantioselective esterases based on molecularly imprinted polymers. Chem Eur J, 2003, 9: 4106–4117

    Article  CAS  Google Scholar 

  28. Say R, Erdem M, Ersoez A, Tuerk H, Denizli A. Biomimetic catalysis of an organophosphate by molecularly surface imprinted polymers. Appl Catal A: Gen, 2005, 286: 221–225

    Article  CAS  Google Scholar 

  29. Ma XM, Xi JY, Huang XB, Zhao X, Tang XZ. Novel hydrophobically modified temperature-sensitive microgels with tunable volume-phase transition temperature. Mater Lett, 2004, 58: 3400–3404

    Article  CAS  Google Scholar 

  30. Li SJ, Pilla S, Gong SQ. Modulated molecular recognition by a temperature-sensitive molecularly-imprinted polymer. J Polym Sci: Part A, 2009, 47: 2352–2360

    Article  CAS  Google Scholar 

  31. Pauling L. Molecular architecture and biological reactions. Chem & Eng News, 1946, 24: 1375–1377

    Article  CAS  Google Scholar 

  32. Lerner RA, Benkovic SJ, Schultz PG. At the crossroads of chemistry and immunology: catalytic antibodies. Science, 1991, 252: 659–667

    Article  CAS  Google Scholar 

  33. Schultz PG. Antibodies as catalysts. Angew Chem, 1989, 101: 1336–1348

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Key Laboratory for Designed Synthesis and Application of Polymer Materials, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, 510275, China

    HongFei Wang, Hao Yang & LiMing Zhang

  2. Key Laboratory for Polymer Composite and Functional Materials, Ministry of Education, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, 510275, China

    HongFei Wang & LiMing Zhang

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  1. HongFei Wang
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  2. Hao Yang
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  3. LiMing Zhang
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Correspondence to LiMing Zhang.

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Wang, H., Yang, H. & Zhang, L. Temperature-sensitive molecularly imprinted microgels with esterase activity. Sci. China Chem. 54, 515–520 (2011). https://doi.org/10.1007/s11426-010-4200-z

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  • DOI: https://doi.org/10.1007/s11426-010-4200-z

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