Abstract:
Trimethyl-lock (TML) quinone acids are able to be functionalised with various compounds, for
example, antibodies, via amide, ester, or thioester bonds, and those attached compounds can be
released from TML molecules at a fast rate under selected conditions, for instance, when the
quinones are electro-reduced. This ability to quickly release compounds has attracted researchers’
attentions to use these molecules for various applications. One application is to attach functionalised
TML quinones to an electric conductive surface, then releasing the bound compounds by applying
reductive potential. Conventional preparation of TML quinone acids, which use chemical oxidants
such as N-bromosuccinimide, were found to be unreliable, which this has severely hindered the
further applications of these molecules.
To overcome this drawback, an alternative TML quinone acid production method, using electrooxidation
(EO), was developed in this project, allowing multiple TML quinone acids to be
successfully synthesised from TML lactones.
Using this developed EO method, it was found that, when these TML were attached on an indium
tin oxide (ITO) surface, the reusability of these molecules was significantly improved.
It was also found that, when this functionalised ITO material is used, the desired release of
compounds is achieved in less harsh conditions and in shorter times, compared to previous methods.
TML molecules were also attached to an electro spun conductive polymer coated fibre mat. Electroreduction
release of molecules from these TML functionalised fibres can be achieved but the release
rate is affected by interactions with the polymer substrate. It was found that the release rate from
these materials can be modified using different solvents and these findings allow the possibility of
using this TML-containing-materials for controlled release of compounds of interest.