4-(2-Amino-1-hydroxyethyl)phenol (octopamine) is a biogenic amine, gained well importance as neuromodulator. This amine plays a certain role in various human disorders such hepatic encephalopathy, schizophrenia, and renal diseases. Due to its stimulating properties, octopamine has been prohibited in elite sports by the World Anti-Doping Agency (WADA) as a specified substance, and several adverse analytical findings (AAFs) of octopamine in doping control samples have been reported during recent years [1]. The determination of octopamine is very difficult because of its presence in very low concentrations in complex samples (plasma or urine).

Molecular imprinting is a synthetic procedure that become an increasingly important technique for the construction of new polymeric materials to selective adsorption of biogenic amines. During this process cavities which are complementary to the template structure are produced. The molecularly imprinted polymers have a great variety of applications in analytical technology (chromatography, solid phase extraction, sensors), drug delivery systems, and organic synthesis.

In presented experiment, 2-amino-1-phenylethanol was selected as the structural analogue of the target analyte, octopamine in the polymerization process. The strategy that used structural analogues during imprinting process is very useful because it enable to avoid the bleeding of target analyte from the polymer matrix during the analysis, what could be the source of overestimated results [2]. We synthetized ten imprinted polymers using different functional monomers. After preliminary estimation of the affinity factors towards octopamine we have chosen polymer with the highest affinity factor for the further analysis. The main part of our experiments were the selectivity measurements using eight different biogenic compounds: octopamine, synephrine, tyramine, N-methyltyramine, hordenine, serotonine, tryptamine, L-tyrosine.   

In the theoretical analysis we have created the model of 2-amino-1-phenylethanol  imprinted polymer cavity using DFT, molecular mechanics and molecular dynamics methods. Next we have analyzed binding energies between eight different analytes  and the polymer matrix to get insight into the selectivity of obtained polymer matrix.

We have obtained good correlation between theoretical (binding energies) and experimental (affinity factors) values. The model of polymer cavity can be used to evaluate recognition properties of the polymer matrix. The proposed procedure could be a very useful theoretical tool for screening the molecularly imprinted systems in the experiment-free way.

References:

[1] MT Thevis, A. Koch, G. Sigmund, A. Thomas, W. Schanzer, Biomed. Chromatogr. 26 (2012) 610-615.

[2] P. Luliński, M. Dana, D. Maciejewska, Talanta 119 (2014) 632-631.

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