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Molecularly imprinted polymers for histamine recognition in aqueous environment

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Abstract

Molecularly imprinted polymers (MIP) for histamine using methacrylic acid were developed and recognition mechanisms were thoroughly characterized for the first time in this study. The binding affinity of imprinted polymer with structurally related compounds was studied in organic and aqueous media, at various conditions. In organic media, MIP was found to bind histamine two and six times more than ranitidine and fluoxetine, respectively, whereas higher selectivity was observed in the case of dimentidene or disodium cromoglycate. The specific binding sites of MIP recognized histamine over l-histidine in aqueous conditions, while higher affinity for histamine compared to ranitidine, disodium cromoglycate, putrescine and to a putrescine analogue was observed. A combination of NMR and UV spectroscopy analyses for investigation of imprinting and recognition properties revealed that strong specific interactions between the functional monomer and histamine in the prepolymerization and in the aqueous solutions were probably responsible for histamine recognition. The preparation of histamine MIPs and elucidation of imprinting and recognition mechanism may serve as useful insight for future application of MIPs.

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Abbreviations

L-His:

l-Histidine

MIP:

Molecularly imprinted polymer

REF:

Reference polymer

PUT:

Putrescine

HI:

Histamine

SPMD:

Spermidine

SPM:

Spermine

MAA:

Methacrylic acid

EDMA:

Ethylene glycol dimethacrylate

TRIM:

Trimethylolpropane trimethacrylate

SPE:

Solid phase extraction

MISPE:

Molecularly imprinted solid phase extraction

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Acknowledgments

This work was supported by the European Union program: Nanoimprinting Technologies for Selective Recognition and Separation, Contract no.: NMP4-CT-2005-516981. This work was part of the EU COST Action BM0806: recent advances in histamine receptor H4R research. F. A. Trikka was a recipient of the Erasmus fellowships. The authors like to thank Professor D. Papaioannou, University of Patras, Greece, for providing the cyclic analogue of putrescine.

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Authors and Affiliations

  1. Laboratory of Biochemistry, Department of Chemistry, Aristotle University of Thessaloniki, 54124, Thessaloniki, Greece

    Foteini A. Trikka & Dimitrios A. Kyriakidis

  2. Pure and Applied Biochemistry, Chemical Center, Lund University, Box 124, 221 00, Lund, Sweden

    Keiichi Yoshimatsu & Lei Ye

Authors
  1. Foteini A. Trikka
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  2. Keiichi Yoshimatsu
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  3. Lei Ye
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  4. Dimitrios A. Kyriakidis
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Correspondence to Dimitrios A. Kyriakidis.

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Trikka, F.A., Yoshimatsu, K., Ye, L. et al. Molecularly imprinted polymers for histamine recognition in aqueous environment. Amino Acids 43, 2113–2124 (2012). https://doi.org/10.1007/s00726-012-1297-8

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  • DOI: https://doi.org/10.1007/s00726-012-1297-8

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