Benzoquinone-based tripartite prodrug delivery systems have been developed to selectively release an active drug under biological conditions. The make-up of the'tripartita delivery asystem is a trigger moiety (quinone) attached to a linker unit (propanoic acid) This is then attached to the active drug via an ester (or amide) link effectively rendering the drug inactive. The aim of this work was to design, synthesise and evaluate a select ct series of prodrug systems and to ascertain whether varying the substituents on the quinone and linker units would enhance the activation of the prodrug and the release of the active ive species following chemical or enzymatic activation.