In photodynamic therapy (PDT), a photosensitizer, light, and oxygen are used to photochemically induce cell death.  Historically, PDT has been used to treat different types of cancers because of the largely selective retention of photosensitizers by malignant tissue.In addition to its use in the treatment of different types of solid cancers of the head, neck, brain, breast and prostate, recently PDT has also been exploited to kill bacterial, fungal and viral infections.  Unfortunately, the limited solubility of most photosensitizers in biological and aqueous media results in the poor delivery of the photosensitizer to the tumor sites. Additionally, most photosensitizers are not entirely selective, a drawback which results in the undesired death of healthy cells.These undesirable properties necessitate the synthesis of new photosensitizers with more ideal properties.  Here we present the modular synthesis of a carbohydrate-porphyrin conjugate that addresses the aforementioned challenges.  In addition to imparting solubility, our current target addresses the selectivity issue by targeting a unique carbohydrate-carbohydrate interaction between Gg3 and GM3 on melanoma cells.  The total synthesis of this conjugate will be discussed as well as future biological applications.

Exploring the use of carbohydrate-carbohydrate interactions in photodynamic therapy using carbohydrate-porphyrin conjugates

247th National Meeting (2014)

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