Synthesis, characterization, and biological properties of a fullerene triphenylphosphonium salt

A monofunctionalised fullerene triphenylphosphonium salt has been synthesised to investigate the potential for adaptation of fullerenes for biological application. The redox properties of fullerenes make them effective radical scavengers and consequently they are potential antioxidants in biological systems. The triphenylphosphonium moiety was chosen because this lipophilic cation increases both the solubility and membrane permeability of attached compounds, and has been used as a delivery agent in biological systems in other contexts. Furthermore, the triphenylphosphonium moiety binds tightly to cognate antibodies, facilitating linkage of attached molecules to proteins. Here we report on the interaction of a triphenylphosphonium fullerene salt with biological systems and its binding of antibodies against the triphenylphosponium moiety.