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Synthesis and characterization of 3-indolylmethanol imprinted polymers

Dorota J. Klejn ,  Piotr Luliński ,  Dorota Maciejewska 

Medical University of Warsaw, Faculty of Pharmacy, Department of Organic Chemistry (WUM), Banacha 1, Warsaw 02-097, Poland

Abstract

Molecularly impinted polymers (MIPs) are modern materials specifically designed for selective and specific recognition of target analytes. MIPs are primarily used as sorbents in bioanalysis and medical diagnostics, as microreactors in organic chemistry, and as carriers used in modern drug delivery systems [1,2].

The synthesis of MIPs involves formation of polymer by combining the template, the functional monomer and solving them in porogenic system prior to copolymerisation that occurs in the presence of cross-linking agent. Once the polymer is formed, the template molecule is then removed from the polymer matrix to create three dimentional cavities that are complementary in shape to the template [1].

3-indolylmethanol (I3C) is a phytochemical that naturally occurs in cruciferous vegetables. After oral administration I3C undergoes dimerization in stomach acid to 3,3'-diindolylmethane (DIM). Both I3C and DIM display multidirectional antitumor activity and are used as a dietary supplements in prevention of tumors [3].

The aim of our work is to produce and characterize 3-indolylmethanol imprinted polymers suitable for selective recognition of I3C. The conducted research will provide a significant contribution to the characterization of imprinting materials of compounds containing indole structure as well as allows selective separation of I3C from biological matrix.

The polymers were prepared by the radical bulk thermal polymerisation. The impact of functional monomer and porogenic solvent was investigated. As functional monomers, we examined acidic monomers (methacrylic acid), basic monomers (allylamine, 4-vinylpyridine), neutral monomers (1,1,1,3,3,3-hexafluoroisopropyl methacrylate).

Our preliminary results show that the highest selectivity (imprinting factor) was achieved for the polymers prepared from 1,1,1,3,3,3-hexafluoroisopropyl methacrylate as well as from allylamine as the functional monomers in carbon tetrachloride as the porogenic solvent. The full set of results and physico-chemical characterization of selected polymers will be presented during the conference.

References:

  1. Luliński P., Polimery (2010), 11–12, 799–805
  2. Luliński P., Polimery (2011), 1, 3–10
  3. Anderton M. et al.,Clin Cancer Res (2004), 10: 5233-5241
 

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Related papers

Presentation: Poster at IX Multidyscyplinarna Konferencja Nauki o Leku, by Dorota J. Klejn
See On-line Journal of IX Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2014-03-15 15:20
Revised:   2014-05-02 11:14