Publication Date


Document Type


First Advisor

Hosmane, Narayan S.

Degree Name

M.S. (Master of Science)

Legacy Department

Department of Chemistry and Biochemistry


A multi-step organic synthetic method to attach carborane cages to biocompatible organic compounds for application in Boron Neutron Capture Therapy (BNCT) was conducted. Boron Neutron Capture Therapy is a form of radiation therapy that promises a new and effective form of cancer treatment that involves the destruction of tumor cells using an isotope of boron (10B). The effectiveness of this therapy depends on the boron content accumulated in cancerous tissue. Carboranes are boron-rich clusters that possess unique physical and chemical properties making them suitable for a wide range of applications including medicinal chemistry. Because of their high boron content, carborane-appended molecules have been synthesized for BNCT application. Levodopa (L-DOPA) is a large neutral amino acid derived from tyrosine and a precursor for catecholamines such as dopamine, norepinephrine, and epinephrine. This amino acid possesses the ability to cross the blood-brain barrier and great biocompatibility. L-DOPA also contains the necessary functional groups found in prostate membrane receptors. Prostate-Specific Membrane Antigen (PSMA) is a membrane expressed in prostate tissue, including carcinoma, and can, therefore, be targeted by using L-DOPA containing PSMA receptor site ligands, followed by the addition of carborane cages. These characteristics of L-DOPA make it a promising carrier molecule for BNCT studies, including the possible treatment of prostate cancer.For this project, an organic synthetic method has been conducted to couple carborane cages to L-DOPA carrier molecules via substitution and click reactions. 1-methyl-o-carborane was used as the boron source compound and attach to L-DOPA to synthesize carborane-appended L-DOPA, as well as carborane-appended L-DOPA conjugated PSMA for BNCT application in the possible brain and prostate cancer treatments, respectively.


62 pages




Northern Illinois University

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