Molecularly imprinted polymers as receptor mimics for selective cell recognition

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Abstract

Molecularly imprinted polymers are now approaching the perfection of natural receptors, e.g., the ability to interact with or recognize cells.

Abstract

Molecularly imprinted polymers (MIPs) have now earned the reputation as “artificial receptors” or “plastic antibodies”. As the mimics of natural receptors, MIPs are reminiscent of some basic functions of natural receptors in living systems, e.g., the ability to interact with or recognize cells. The latest decade has witnessed a great advance in MIPs from simple molecular extraction to efficient cell recognition, implying that MIP-based synthetic receptors are approaching to be perfectly functioning replicates of their natural counterparts. With the most emerging development in molecular imprinting, MIP-mediated cell recognition has now shown great promise in cell biology research, theranostics and regenerative medicine. This tutorial review provides a panoramic view of current MIPs for both microorganism and mammalian cell recognition. The most representative developments of MIP-mediated cell recognition, from initial imprinting strategies to eventual bio-related applications, are highlighted.

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Molecular recognition in chemical and biological systems.

Elke Persch, Oliver Dumele, François Diederich (2015)

Structure-based ligand design in medicinal chemistry and crop protection relies on the identification and quantification of weak noncovalent interactions and understanding the role of water. Small-molecule and protein structural database searches are important tools to retrieve existing knowledge. Thermodynamic profiling, combined with X-ray structural and computational studies, is the key to elucidate the energetics of the replacement of water by ligands. Biological receptor sites vary greatly in shape, conformational dynamics, and polarity, and require different ligand-design strategies, as shown for various case studies. Interactions between dipoles have become a central theme of molecular recognition. Orthogonal interactions, halogen bonding, and amide⋅⋅⋅π stacking provide new tools for innovative lead optimization. The combination of synthetic models and biological complexation studies is required to gather reliable information on weak noncovalent interactions and the role of water.

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Sialic Acid-Imprinted Fluorescent Core-Shell Particles for Selective Labeling of Cell Surface Glycans.

Sudhirkumar Shinde, Zahra El-schich, Atena Malakpour … (2015)

The expression of cell surface glycans terminating with sialic acid (SA) residues has been found to correlate with various disease states there among cancer. We here report a novel strategy for specific fluorescence labeling of such motifs. This is based on sialic acid-imprinted core-shell nanoparticles equipped with nitrobenzoxadiazole (NBD) fluorescent reporter groups allowing environmentally sensitive fluorescence detection at convenient excitation and emission wavelengths. Imprinting was achieved exploiting a hybrid approach combining reversible boronate ester formation between p-vinylphenylboronic acid and SA, the introduction of cationic amine functionalities, and the use of an NBD-appended urea-monomer as a binary hydrogen-bond donor targeting the SA carboxylic acid and OH functionalities. The monomers were grafted from 200 nm RAFT-modified silica core particles using ethylene glycol dimethacrylate (EGDMA) as cross-linker resulting in a shell thickness of ca. 10 nm. The particles displayed strong affinity for SA in methanol/water mixtures (K = 6.6 × 10(5) M(-1) in 2% water, 5.9 × 10(3) M(-1) in 98% water, B(max) ≈ 10 μmol g(-1)), whereas binding of the competitor glucuronic acid (GA) and other monosaccharides was considerably weaker (K (GA) = 1.8 × 10(3) M(-1) in 98% water). In cell imaging experiments, the particles selectively stained different cell lines in correlation with the SA expression level. This was further verified by enzymatic cleavage of SA and by staining using a FITC labeled SA selective lectin.