One of the main challenges with new pharmaceuticals is delivery. Many drugs that display high activity are lipophilic; however, to deliver these molecules, they must also be hydrophilic. One method to increase the aqueous solubility of pharmaceuticals is through the utilization of cyclic chlorophosphazenes as a drug delivery system. Cyclophosphazenes are a model system for this delivery for several reasons, one being the ease at which the phosphorus atoms of the ring structure can be substituted with a wide variety of side groups. We have synthesized a hydrophilic phosphazene-based system by substituting three equivalents of tetraethyleneglycol monomethyl ether (TEGME) onto the phosphazene trimer ring ([PCl<sub>2</sub>N]<sub>3</sub>). Following the addition of TEGME, the phosphazene rings system contains additional sites for further modification and substitution. These sites can be substituted with imaging agents, anti-cancer agents, and targeting moieties. We are currently investigating the efficacy of substituting targeting moieties (triphenylphosphonium cations) to the previously synthesized phosphazene system. Triphenylphosphonium-based compounds have demonstrated effectiveness in targeting mitochondria in cancer cells. By substituting triphenylphosphonium cations to the cyclophosphazene system, the efficacy of the compound may increase while also decreasing toxicity. The results of this study were characterized via multi-nuclear NMR studies.

Design and synthesis of cyclophosphazene drug delivery systems incorporating triphenylphosphonium cations as targeting moieties

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.