Chemistry and Biochemistry
Dr. Thomas Hagan
Porphyrins are macrocyclic compounds that can be synthesized and used in photodynamic therapy (PDT), a noninvasive and selective method designed to eliminate diseased tissue (such as cancer) without killing healthy tissue. PDT involves the following three steps. A photosensitizer enters a cancerous cell, is excited by electromagnetic radiation, and transfers the energy to molecular oxygen which is then converted into singlet oxygen, which triggers cellular apoptosis. However, for a porphyrin to be utilized as a therapeutic in PDT, it must satisfy the following two criteria: the porphyrin needs to possess the correct solubility to pass through the cell membrane and absorb the specific wavelength of electromagnetic radiation that penetrates through human tissue, approximately 620 - 730 nm. The focus of our studies revolves around synthesizing a porphyrin species that meets the two parameters mentioned above. Porphyrins exhibit absorbance in this redlight range due to their structure, however, to achieve the required solubility to transverse the lipid bilayer, a fatty acid like molecule will be coupled to the porphyrin. The 5,10,15-Triphenyl-20-[4-(carboxy)phenyl] porphyrin, Isomer 1, is ideal for this experiment because there is only one position where the attachment can occur.
Davis, William J., "Synthesis of Asymmetrically-Substituted Tetraphenyl-Class Porphyrins" (2022). Summer Scholarship, Creative Arts and Research Projects (SCARP). 46.
Scholarship, Creative Arts, and Research Project (SCARP)