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. 2018;30(11):929-939.
doi: 10.1080/10610278.2018.1489540. Epub 2018 Jul 20.

Surface Ligands in the Imprinting and Binding of Molecularly Imprinted Cross-Linked Micelles

M D Arifuzzaman  1 , Wei Zhao  1 , Yan Zhao  1
Affiliations

Surface Ligands in the Imprinting and Binding of Molecularly Imprinted Cross-Linked Micelles

M D Arifuzzaman et al. Supramol Chem. 2018.

Abstract

Molecular recognition in water is challenging but water-soluble molecularly imprinted nanoparticle (MINP) receptors were produced readily by double cross-linking of surfactant micelles in the presence of suitable template molecules. When the micellar surface was decorated with different polyhydroxylated ligands, significant interactions could be introduced between the surface ligands and the template. Flexible surface ligands worked better than rigid ones to interact with the polar moiety of the template, especially for those template molecules whose water-exposed surface is not properly solvated by water. The importance of these hydrophilic interactions was examined in the context of different substrates, density of the surface ligands, and surface-cross-linking density of the MINP. Together with the hydrophobic interactions in the core, the surface hydrophilic interactions can be used to enhance the binding of guest molecules in water.

Keywords: binding; cross-linking; micelle; molecular imprinting; nanoparticle.

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Figures

Figure 1.
Figure 1.
(a) Emission spectra of compound 7 in the presence of 0–1.7 μM of MINP3(7) in Millipore water. [7] = 0.5 μM. λex = 340 nm. (b) Nonlinear least squares curve fitting of the fluorescence intensity at 491 nm to a 1:1 binding isotherm.
Figure 2.
Figure 2.
ITC curve obtained at 298 K from titration of MINP3(7) with 7 in Millipore water. MINP3(7) = 10 μM in the cell. The concentration of 7 in the syringe was 0.20 mM.
Figure 3.
Figure 3.
Proposed binding of template 7 by MINP3(7), with possible hydrogen bonds between the surface ligand and the hydrophilic groups of the template, possibly also mediated by water molecules.
Figure 4.
Figure 4.
Schematic representation of the cross-linking and surface ligands in MINP3,2 (a) and MINP3,10 (b).
Scheme 1.
Scheme 1.
Preparation of MINP by surface-cross-linking of the micelle of 1, surface decoration of the alkynyl-surface-cross-linked micelle (alkynyl-SCM) by ligand 3, and core-cross-linking of the resulting material.
Scheme 2.
Scheme 2.
Synthesis of cross-linker 10 containing a sugar-derived group.
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