Article
  • Synthesis of Molecularly Imprinted Polymers for Chiral (S)-Ibuprofen and Their Molecular Recognition Mechanism
  • Huangfu F, Wang B, Sun Y
  • 키랄(S)-이부푸로펜 함유 고분자의 합성과 제조된 고분자의 분자 인식 메카니즘
  • Huangfu F, Wang B, Sun Y
Abstract
A group of molecularly imprinted polymers (MIPs) with specific recognition for chiral (S)-ibuprofen were successfully prepared based on hydrogen bonds, utilizing α-methacrylic acid as a functional monomer. The IR analysis of MIPs showed that the blue- and red-shifted hydrogen bonds were formed between templates and functional monomers in the process of self-assembly imprinting and re-recognition, respectively. According to UV-Vis analysis, we found that the ratio of host-guest complexes between template molecule and functional monomer was 1:1. The effect of crosslinker's quantity on the polymerization was studied by transmission electron microscope (TEM). The adsorption selectivity experiments indicated that MIPs exhibited higher selectivity to (S)-ibuprofen than those to ketoprofen and (R)-ibuprofen, (S)-ibuprofen's structural analogs.

Keywords: (S)-ibuprofen; molecularly imprinted polymer; chiral separation; hydrogen bond; separation factor.

References
  • 1. Chen LX, Xu SF, Li JH, Chemical Society Reviews., 40, 2922 (2011)
  •  
  • 2. Jung YH, Lee JW, Yoo YT, Polym.(Korea), 36(4), 434 (2012)
  •  
  • 3. Shi HQ, Tsai WB, Garrison MD, Ferrari S, Ratner BD, Nature., 398, 593 (1999)
  •  
  • 4. Andersson LI, J. Chromatogr. B., 745, 3 (2000)
  •  
  • 5. Apodaca DC, Pernites RB, Ponnapati R, Del Mundo FR, Advincula RC, Macromolecules, 44(17), 6669 (2011)
  •  
  • 6. Alexander C, Andersson HS, Andersson LI, Ansell RJ, Kirsch N, Nicholls IA, O'Mahony J, Whitcombe MJ, J.Mol. Recognit., 19, 106 (2006)
  •  
  • 7. Ameli A, Alizadeh N, Anal. Biochem., 428, 99 (2012)
  •  
  • 8. Lin LQ, Li YC, Fu Q, He LC, Zhang J, Zhang QQ, Polymer, 47(11), 3792 (2006)
  •  
  • 9. Bowen WR, Nigmatullin RR, Sep. Sci. Technol., 37(14), 3227 (2002)
  •  
  • 10. Ebeshi BU, Oseni KE, Ahmadu AA, Oluwadiya JO, Afr. J. Pharm. Pharmacol., 3, 426 (2009)
  •  
  • 11. Ezzat T, van den Broek MAJ, Davies N, Dejong CHC, Bast A, Malago M, Dhar DK, Damink S, J. Surg. Oncol., 106, 72 (2012)
  •  
  • 12. Aitipamula S, Desiraju GR, Jaskolski M, Nangia A, Thaimattam R, Cryst. Eng. Comm., 5, 447 (2003)
  •  
  • 13. Kim Y, Chang JH, Polym.(Korea), 36(4), 478 (2012)
  •  
  • 14. Kim DK, Park SD, Oh JW, Kyoung JB, Polym.(Korea), 36(4), 413 (2012)
  •  
  • 15. Holland N, Frisby J, Owens E, Hughes H, Duggan P, McLoughlin P, Polymer, 51(7), 1578 (2010)
  •  
  • 16. Zhao KY, Cheng GX, Huang JJ, Ying XG, React.Funct. Polym., 68, 732 (2008)
  •  
  • 17. Del Blanco SG, Donato L, Drioli E, Sep. Purif. Technol., 87, 40 (2012)
  •  
  • 18. Gupta R, Kumar A, J. Sol-Gel Sci. Techn., 58, 182 (2011)
  •  
  • 19. Alabugin IV, Manoharan M, Peabody S, Weinhold F, J. Am. Chem. Soc., 125(19), 5973 (2003)
  •  
  • 20. Hermansson K, J. Phys. Chem. A, 106(18), 4695 (2002)
  •  
  • 21. Scheiner S, Kar T, J. Phys. Chem. A, 106(9), 1784 (2002)
  •  
  • Polymer(Korea) 폴리머
  • Frequency : Bimonthly(odd)
    ISSN 0379-153X(Print)
    ISSN 2234-8077(Online)
    Abbr. Polym. Korea
  • 2022 Impact Factor : 0.4
  • Indexed in SCIE

This Article

  • 2013; 37(3): 288-293

    Published online May 25, 2013

  • Received on Sep 6, 2012
  • Accepted on Dec 2, 2012