A Route to Water-Soluble Molecularly Templated Nanoparticles Using Click Chemistry and Alkyne-Functionalized Hyperbranched Polyglycerol

Cored polymeric nanoparticles were prepared using an adenosine template and allylated hyperbranched polyglycerols (HPGs). The HPGs contained a single alkyne that was capable of 1,3-dipolar cycloaddition with a decaazido adenosine template to facilitate the rapid synthesis of HPGs containing a large number of allyl end-groups. Ring closing metathesis (RCM) mediated cross-linking at high dilution using a Hoveyda–Grubbs catalyst produced single polymer nanoparticles containing a single template. These particles were rendered water-soluble through treatment with osmium tetroxide and NMO co-oxidant. After hydrolytic removal of the template, the nanoparticles were tested for their ability to bind a variety of nucleosides and nucleobases and showed a preference for purine bases over pyrimidine bases. This is the first reported use of hyperbranched polymers for the synthesis of monomolecularly imprinted polymers (mMIPs) as well as the first time monomolecular imprinting has been applied to a homogeneous aqueous system.