Photodynamic therapy (PDT) is a cancer treatment inspired by the photosensitive qualities of large aromatic molecules in the tetrapyrrole family. Currently, porphyrins, such as Photofrin, are the most widely used PDT photosensitizer for cancer treatment, though the structure of the molecule creates limitations in its clinical use. Bacteriochlorins have been explored as possible photosensitizers for PDT since they more closely meet the desired traits of an optimal PDT agent, such as deeper tissue penetration, lower photosensitivity, and intense absorption in the near infrared wavelength range. However, a drawback of using bacteriochlorins is that, relative to porphyrins, the synthesis is lengthy and complicated. Thus, one focus of our research was to evaluate several published methods for alkynylated bacteriochlorin synthesis; the most successful of which was utilized in our subsequent research. The ultimate goal of our research was the synthesis of an azido-carbohydrate glycoconjugated bacteriochlorin via a 1,3-dipolar cycloaddition reaction, otherwise known as a “click reaction”. Click reactions lead to the formation of an aromatic triazole ring, which could shift the absorbance wavelength of the bacteriochlorin to a higher, even more desirable wavelength in the near infrared. In the end, glycoconjugated bacteriochlorins with mono- and di-saccharides were successfully synthesized and characterized.

Developing methods for the synthesis of bacteriochlorin-glycoconjugates

2019 Spring National Meeting

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