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Abstract: A molecularly imprinted polymer (MIP) enantioselective receptor for the (R)-thalidomide enantiomer was synthesized and evaluated for its ability to deliver the drug to cancer cells. Polymer networks with precisely engineered binding sites were built into the assembled nanoparticles by a self-organizing template in the prepolymerized mixture using methacrylic acid, a fluorescently active 2,6-bis(acrylamido)pyridine and N,N' methylene-bis-acrylamide, via both a covalent approach and a physical approach. The fine-tuning of particle diameters was carried out by changes to the polymerizing synthesis method, the type of solvent and the amount of the poloxamer that led to an optimal formulation of the nanoparticles with sizes as small as 100 nm. Data from the 1H-nuclear magnetic resonance spectroscopy revealed the important structural motifs of an (R)-thalidomide-selective cavity for two different polymerization processes. We have investigated their ability for enantiomer recognition and the potential ability to protect the chiral MIP with a self-assembled poloxamer structure. Moreover, the effect of the smaller molecular size can not only enable favorable imaging properties but also facilitate enhanced green fluorescence intensity for the deposited MIP and the (R)-thalidomide in the poloxamer nanoparticles in a cell-line in which the grafted MIP being higher than the deposited one. It was also demonstrated that the deposited MIP nanoparticles had the potential to make the drug effective for attacking multidrug-resistant cells. Thus, the poloxamer nanoparticles containing a thermoresponsive MIP could maximize the release of the nontoxic (R)-thalidomide at the tumor tissue, with the help of a proper temperature shift at the site. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 41930
Template and target information: (R)-thalidomide, thalidomide
Author keywords: biomimetic, molecular recognition, self-assembly, stimuli-sensitive polymers