The Facile Synthesis of a Far-Red ER-Targeting BODIPY Dye Capable of Light Induced Reactive Oxygen Species Generation

Date of Award

5-1-2025

Degree Name

M.S. in Chemistry

Department

Department of Chemistry

Advisor/Chair

Shawn Swavey

Abstract

Photodynamic therapy (PDT) is an exciting and emerging field of cancer treatment that acts in a much more selective manner via targeted cellular localization and localized irradiation to activate a photosensitizing drug in order to generate reactive oxygen species (ROS) that ultimately lead to cell death. Evidence has suggested that the endoplasmic reticulum (ER), one of the largest and most important cellular organelles, could be an important target in PDT. Interested in that idea, and to the ends of creating new photosensitizers (PS) that might accomplish this goal, a new far-red light activated iodo-substituted boron dipyrromethene (BODIPY) fluorescent dye capable of subcellular localization within the ER, producing high quantum yields of ROS is herein reported. As such, the following research has found that the generation of reactive oxygen species within the ER, caused by this BODIPY (BDP-1I) evokes oxidative stress, which in turn causes immunogenic cell death. The synthesis, characterization, spectroscopic properties, and cellular studies are thoroughly presented. The ability of this BODIPY dye, and its congener (BDP-1), to act as a PDT agent in breast cancer cells suggests promising organelle-targeted therapeutics that could help push the field of PDT to new heights.

Keywords

Chemistry

Rights Statement

Copyright 2025, author.

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