Guiding Molecularly Imprinted Polymer Design by Pharmacophore Modeling

Wiebke Derz; Melita Fleischmann; Paul W Elsinghorst

doi:10.3390/molecules26165101

Guiding Molecularly Imprinted Polymer Design by Pharmacophore Modeling

Molecules. 2021 Aug 23;26(16):5101. doi: 10.3390/molecules26165101.

Authors

Wiebke Derz^{1

2}, Melita Fleischmann^{1

3}, Paul W Elsinghorst^{1

2

4}

Affiliations

¹ Central Institute of the Bundeswehr Medical Service Munich, 85748 Garching, Germany.
² Institute of Nutrition and Food Sciences, University of Bonn, 53115 Bonn, Germany.
³ Food Technology & Nutrition, Management Center Innsbruck, 6020 Innsbruck, Austria.
⁴ Pharmaceutical Chemistry I, Pharmaceutical Institute, University of Bonn, 53121 Bonn, Germany.

Abstract

Molecularly imprinted polymers (MIP) combine the selectivity of immunoaffinity chromatography with the robustness of common solid-phase extraction in what is referred to as molecularly imprinted solid-phase extraction (MISPE). This contribution shows how MIP design may be guided by pharmacophore modeling for the example of citrinin, which is an emerging mycotoxin from cereals. The obtained pharmacophore model allowed searching public databases for a set of citrinin-mimicking molecular surrogates. Imprinted and non-imprinted polymers were subsequently obtained through bulk and core-shell polymerization in the presence of these surrogates. Evaluation of their binding ability for citrinin and structurally related ochratoxin A revealed a promising MIP derived from rhodizonic acid. A protocol for MISPE of citrinin from cereals was subsequently developed and compared to immunoaffinity chromatography with respect to clean-up efficiency and recovery.

Keywords: MIP; MISPE; citrinin; core-shell polymers; molecularly imprinted polymers; mycotoxins; pharmacophore modeling.