Electrochemically initiated release: exploring new modalities for controlled drug release

Abstract

A series of naphthoquinone-aminophenol derivatives have been synthesized on the basis that their conjugation with a suitable drug candidate could provide a means through which the latter could be released upon the imposition of an appropriate oxidation potential. The approach is based on a three component assembly in which the naphthoquinone redox centre serves as a reporter unit allowing electrochemical interrogation without release of the drug. The central aminophenol serves as the tether to which the drug is linked via an ether bond. Upon oxidation of the aminophenol - ether component, transition of the latter to quinone imine results in the release of the drug. The electrochemical properties of the model system are investigated and the impact of the release process on the functional groups intrinsic to the drug component is critically considered.