Polymeric Nanoparticle Receptors as Synthetic Antibodies for Nonsteroidal Anti-Inflammatory Drugs (NSAIDs)

Abstract

The wide usage and subsequent leakage of nonsteroidal anti-inflammatory drugs (NSAIDs) into the environment present an urgent need to create materials for selective binding of NSAID drugs, which are highly similar to one another in structure and functionality. Surface-core double-cross-linking of cationic micelles containing Naproxen or Indomethacin as the template yielded molecularly imprinted nanoparticles (MINPs) for these drugs. The nanoparticle receptors resembled water-soluble proteins in their hydrophilic exterior and hydrophobic core with guest-tailored binding pockets. Their binding selectivity for their templates over other NSAID analogues rivaled that of antibodies prepared through much lengthier procedures. ABSTRACT: The wide usage and subsequent leakage of nonsteroidal anti-inflammatory drugs (NSAIDs) into the environment present an urgent need to create materials for selective binding of NSAID drugs, which are highly similar to one another in structure and functionality. Surface−core double-cross-linking of cationic micelles containing Naproxen or Indomethacin as the template yielded molecularly imprinted nanoparticles (MINPs) for these drugs. The nanoparticle receptors resembled water-soluble proteins in their hydrophilic exterior and hydrophobic core with guesttailored binding pockets. Their binding selectivity for their templates over other NSAID analogues rivaled that of antibodies prepared through much lengthier procedures.

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.…”

“…We have confirmed in many studies that binding constants obtained by ITC agreed with those by other methods such as fluorescence titration. 30–34 …”

“…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.…”

“…Although the micelles are highly cross-linked, because polymerization and cross-linking are confined within the micellar boundary, MINPs are fully soluble in water due to their hydrophobic/hydrophilic core–shell morphology and nanodimension (4–5 nm). Using this technique, we have created strong and selective receptors for a number of different guests including bile salt derivatives, 30 aromatic carboxylates and sulfonates, 31–33 nonsteroidal anti-inflammatory drugs (NSAIDs), 34 carbohydrates, 35, 36 and oligopeptides. 37 …”