Date of Award

4-16-2021

Document Type

Thesis

Department

Chemistry

First Reader

Dr. Joseph Bradshaw

Second Reader

Dr. Tim Hayes

Third Reader

Dr. Amy Sonheim

Abstract

Triple-Negative Breast Cancer (TNBC) accounts for upwards of 15% of reported breast cancer cases. This subtype of breast cancer poses a greater threat to those diagnosed as compared to other types of breast cancer due to the lack of treatment options available. Additionally, TNBC grows and spreads faster, tends to be more aggressive, and has a greater chance of recurrence than its counterparts. Altogether, TNBC cases generally have a worse prognosis over other types of breast cancer. Photodynamic therapy (PDT) is currently being researched as a way to treat TNBC. Photodynamic therapy agents are light-activated materials used for localized disease treatment. The compounds known as porphyrins are notable examples of photosensitive agents. Through this project, the novel, water-soluble porphyrin derivative H2TPP-MorphMeOH was synthesized from the starting materials, H2TPPC and the amine morpholin-2-yl methanol. Following the synthesis, the compound was purified through liquid chromatography, and then characterized using infrared (IR), nuclear magnetic resonance (NMR), and UV-Vis spectroscopies, and High-Performance Liquid Chromatography (HPLC). Lastly, to determine its utility as a PDT agent, the cytotoxicity of H2TPP-MorphMeOH was determined using an MTT assay on MDA-MB-231 TNBC cells in the presence and absence of white light.

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