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Selective recognition in molecularly imprinted polymer and its chromatographic characterization for cinchonine

  • Zhong Shi-an Email author
  • Huang Ke-long 
  • Lei Qi-fu 
  • Xiang Hai-yan 
Mineral Processing, Metallurgy And Chemistry

Abstract

A molecularly imprinting polymer (MIP) was synthesized via bulk polymerization under different conditions using anti-ague drug cinchonine (CN) as template. Infrared spectra (IR) results show that the template CN and functional monomer α-methyl acrylic acid (MAA) formed complexes before polymerization and the structure of complexes was simulated by Hyperchem. The results indicate that there are hydrogen bond or ionic bond between functional monomer and template molecule in acetonitrile solution. The MIP made in cold-initiated photo-polymerization has higher separation performance than that in the therm-initiated polymerization. The separation of the isomers CN and cinchonidine (CD) can be successfully obtained when its separate factor α reaches 1.82. Scatchard analysis suggests that the MIP recognizing CN with two classes of binding sites. The partition coefficient Kd, 1 and apparent maximum number nmax, 1 of binding sites with high affinity are 131.43 µmol/L and 58.90 µmol/g, respectively, while Kd, 2 and nmax, 2 of binding sites with low affinity are 2.32 mmol/L and 169.08 mmol/g, respectively.

Key words

molecular imprinting cinchonine chiral separation HPLC 

CLC number

O657. 72 

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References

  1. [1]
    Mosback K, Ramston O. The emerging technique of molecular imprinting and its future impact on biotechnology[J]. Biotechnology, 1996, 14: 163–170.Google Scholar
  2. [2]
    MENG Zi-hui, WANG Jin-fang, ZHOU liang-mo, et al. Progress of molecule imprinting technique[J]. Progress in Chemistry, 1999, 11(4): 358–366. (in Chinese)Google Scholar
  3. [3]
    Hirayama K, Sakai Y, Kameoka K, et al. Preparation of a sensor device with specific recognition sites for acetaldehyde by molecular imprinting technique[J]. Sensors and Actuators B, 2002, 86: 20–25.CrossRefGoogle Scholar
  4. [4]
    Toorisaka E, Uezu K, Goto M, et al. A molecular imprinted polymer that shows enzymatic activity[J]. Biochemical Engineering Journal, 2003, 14: 85–91.CrossRefGoogle Scholar
  5. [5]
    MENG Ling-zhi, YU Zhao-ju, YUAN Liang-jie. Preparation and recognition of dyes molecular imprinting silicone(I)[J]. J Wuhan Univ (Nat Sci ED), 2002, 48(2): 147–150. (in Chinese)Google Scholar
  6. [6]
    Theodoridis G, Manesiotis P. Selective solid-phase extraction sorbent for caffeine made by molecular imprinting[J]. Journal of Chromatography A, 2002, 948: 163–169.CrossRefGoogle Scholar
  7. [7]
    Hentze H P, Antoniett M. Porous polymers and resins for biotechnological and biomedical applications[J]. Reviews in Molecular Biotechnology, 2002, 90: 27–53.CrossRefGoogle Scholar
  8. [8]
    WANG Jin-fang, ZHOU Liang-mo, LIU Xue-liang, et al. Simultaneous chiralseparation of two pairs of enantiomers using series column of molecular imprinted phase[J]. Journal of Analytical Chemistry, 2000, 28(9):1096–1098. (in Chinese)Google Scholar
  9. [9]
    LU Yan, LI Chen-xi, ZHANG He-sheng, et al. Study on the mechanism of chiral recognition with molecularly imprinted polymers[J]. Analytica Chimica Acta, 2003, 489:33–43.CrossRefGoogle Scholar
  10. [10]
    Reddy P S, Kobayashi T, Abe M, et al. Molecular imprinted nylon-6 as a recognition material of amino acids[J]. European Polymer Journal, 2002, 38:521–529.CrossRefGoogle Scholar
  11. [11]
    Coutinho D, Acevedo A O, Dieckmann G R, et al. Molecular imprinting of mesoporous SBA-15 with chiral ruthenium complexes[J]. Microporous and Mesoporous Materials, 2002, 54: 249–255.CrossRefGoogle Scholar
  12. [12]
    SUN Rui-feng, LUO Hui, SUI Hong-yan, et al. Application of stoichiometric displacement model for retention to the chromatographic separation by molecular imprinting polymer[J]. Journal of Progress Engineering, 2003, 3(2): 165–170. (in Chinese)Google Scholar
  13. [13]
    DU Xiao-yan, PENG Tao, LI Jun-suo. Preparation and binding characteristics of molecularly imprinted polymer for sarafloxacin[J]. Journal of Analytical Chemistry, 2003, 31(6): 720–722. (in Chinese)Google Scholar
  14. [14]
    Theodoridis G, Kantifes A, Manesiotis P, et al. Preparation of a molecularly imprinted polymer for the solid-phase extraction of scopolamine with yoscyamine as a dummy template molecule[J]. Journal of Chromatography A, 2003, 987: 103–109.CrossRefGoogle Scholar
  15. [15]
    LI Ping, SHEN Xun-wei, XIE Yi-bing, et al. Synthesis of molecular imprinting polymer and its application in chiral separation for phenylalanine etnylesters[J]. Journal of Analysis Laboratory, 2002, 21(2): 12–14. (in Chinese)Google Scholar

Copyright information

© Central South University 2005

Authors and Affiliations

  • Zhong Shi-an 
    • 1
    Email author
  • Huang Ke-long 
    • 1
  • Lei Qi-fu 
    • 1
  • Xiang Hai-yan 
    • 1
  1. 1.School of Chemistry and Chemical EngineeringCentral South UniversityChangshaChina

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