Synthesis and characterization of carborane-appended biomolecules

Advisors: Narayan S. Hosmane.Committee members: Timothy J. Hagen; Lee S. Sunderlin.A multi-step organic synthetic methodology to attach multiple boron-containing carborane cages (boron source) to suitable biocompatible organic compounds (carriers) that can be used for boron neutron capture therapy (BNCT) applications has been established1. The method involves alkylation of the selected organic compounds followed by conjugation with a polyhedral carborane cage using a click reaction2, 3(see scheme 1). To date, carborane derivatives of 4-nitroimidazole, 2-nitroimidazole, phenothiazine, 1, 3, 4-thiadiazole-2, 5-dithiol, adenine, 6-chloropurine and 3', 5'-dihydroxyacetophenone have been successfully synthesized. In addition, different coumarin derivatives were successfully synthesized using click chemistry. All products were purified and isolated in good yields and characterized using Fourier-Transform Infrared Spectroscopy (FTIR), Nuclear Magnetic Resonance (NMR), elemental analysis and Mass Spectrometry (MS). These products could be made water soluble by decapitation of the carborane cage in order for their biological evaluation.M.S. (Master of Science