Phthalocyanines, porphyrins, and bacteriochlorin’s are heterocyclic macrocycles that generate cytotoxic reactive oxygen species when exposed to specific wavelengths of light. Such compounds have proven useful as phototherapeutics in the treatment of bacterial infections and cancer. However, research in this area has been hindered by the hydrophobicity of these compounds, which limits their solubility in biological (aqueous) fluids, and their lack of specificity, which can lead to the unwanted death of healthy cells. In our efforts to address these challenges, we are currently synthesizing carbohydrate phthalocyanine conjugates (CPcC’s). The carbohydrate component, which naturally imparts solubility, can also be designed to impart specificity. The phthalocyanine component serves as a near infrared (NIR) theranostic for diagnosis and photodynamic therapy (PDT) treatment. Here we present our novel modular two-step method for the synthesis of CPcC’s using a Cu-catalyzed 1,3-dipolar cycloaddition reaction, or “click” reaction, as the key step.

Synthesis of carbohydrate phthalocyanine conjugates

251st National Meeting (2016)

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