We studied a panel of thermally sensitive amino-esters and amino-carbonates to evaluate their cyclization rates on heating.  After analyzing the influence of chain length, steric factors, gem-dimethylation and additional functionalities, we have determined which ester and carbonate configurations are well-suited to undergo intramolecular nucleophilic attack by pendant amines.  In this event, the formation of the lactam or cyclic carbamate product releases an alcohol substrate, and this step is of interest as a potential drug delivery mechanism.  Since Fe3O4 nanoparticles (NPs) readily heat when placed in an alternating magnetic field (AMF), we examined whether this magnetic field-induced heat could be used to trigger the aforementioned ring-closures.  We present here our efforts to covalently attach the amino-substrates to NPs and the results of AMF exposure on the loaded NPs.

Thermally labile amino-ester and amino-carbonate linkers for AMF-induced drug release from iron oxide nanoparticles

246th National Meeting (2013)

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