Water‐Soluble Molecularly Imprinted Nanoparticles (MINPs) with Tailored, Functionalized, Modifiable Binding Pockets

Abstract

Construction of receptors with binding sites of specific size, shape, and functional groups is important to both chemistry and biology. Covalent imprinting of a photocleavable template within surface-core doubly cross-linked micelles yielded carboxylic acid-containing hydrophobic pockets within the water-soluble molecularly imprinted nanoparticles. The functionalized binding pockets were characterized by their binding of amine- and acid-functionalized guests under different pH values. The nanoparticles, on average, contained one binding site per particle and displayed highly selective binding among structural analogues. The binding sites could be modified further by covalent chemistry to modulate their binding properties.

Imprinted micelles for chiral recognition in water: shape, depth, and number of recognition sites

“…30–32, 34 For example, 1 H NMR allowed us to monitor the surface- and core-cross-linking (ESI). Dynamic light scattering (DLS) afforded the size of the nanoparticles, as well as their average molecular weights.…”

“…Because the binding took place in water, hydrophobic interactions have been shown to dominate the binding of MINPs according to our recent studies. 30–32, 34 For compounds 4 and 5 , the two benzoyl groups are obvious points of interactions as a result of hydrophobic imprinting. The third interaction, most likely, comes from the carboxylate, which could ion-pair with a nearby ammonium headgroup of the cross-linked 1 .…”

“…30–32, 34 There are two considerations for the choice. First, the incorporation of a hydrophobic anionic template into the cationic micelle of 1 is favored by both electrostatic and hydrophobic interactions.…”

Molecularly Responsive Binding through Co-occupation of Binding Space: A Lock–Key Story

“…In the final step of the preparation, we cleaved the ortho -nitrobenzyl ester bond by photolysis to remove the template, creating a template-complementary binding pocket within the doubly cross-linked micelle (Scheme 1). 7 …”

“…7 An important feature of the MINP receptors is the controllable number of binding sites on the nanoparticle. Since each SCM contains ca.…”