Doctor of Philosophy (PhD)



Document Type



The goal of the research presented in this dissertation is to develop novel water soluble carboranylporphyrins that can deliver therapeutic dosage of boron specifically to tumors for application in boron neutron capture therapy. In order to accomplish this goal novel water soluble tetra(nido-carboranyl)porphyrin and the octa(nido-carboranyl)porphyrin with high boron contents are synthesized by the condensation of the carborane substituted benzaldehyde with the pyrrole under acidic conditions. These porphyrins are made water soluble by the deboronation of the closo-carboranes to afford the corresponding amphiphilic nido-carborane cages. The low cytotoxicity, high cellular uptake and intracellular localization of these carboranylporphyrins in tumor cells are accomplished. The synthesis of the tetra(4-nido-carboranylphenyl)porphyrin is also accomplished and the comparative biological evaluation of the tetra(4-nido-carboranylphenyl)porphyrin and the tetra(carboranylphenyl)tetrabenzoporphyrin in the tumor cells show lower toxicity and better uptakes of these porphyrins in the cells. These porphyrins also show low toxicity in the mice. The syntheses of various novel neutral water soluble carboranylporphyrins is accomplished. These novel carboranylporphyrins synthesized are water-soluble by the functionalization of the carboranes with water-solubilizing groups such a polyethylene glycol, hydroxyl and amine groups. The synthesis of novel carboranylsapphyrins is attempted. Sapphyrins are penta pyrrolic macrocycles and various methods for the synthesis of these macro cycles are attempted and reported.



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Committee Chair

M. Graca H. Vicente

Included in

Chemistry Commons