Research in my group is centered around the synthesis and properties of macrocycles related to porphyrins, calixarenes and the enediyne anti-tumor antibiotics. We are interested in fine-tuning the properties of porphyrins and calixarenes by developing synthetic methods to systematically replace the bridging carbon atoms in these macrocycles with nitrogen atoms. This substitution can have a profound effect on the electronic and physical properties of these macrocylces and offer new motifs for their functionalization. We are also currently developing synthetic strategies to utilize porphyrin macrocylces to deliver and activate enediyne pro-drugs towards Bergman cyclization. The connection of a porphyrin macrocycle with an enediyne pro-drug, generating a family of compounds we refer to as porphyrenediynes, introduces a number of advantages for drug delivery such as water solubility, DNA binding, tumor selectivity and improved photo-activation through substituents on the porphyrin. Some of the compounds we are working on in the laboratory are shown below. For a complete description of these research projects see our research group page.
