The synthesis, photophysical properties, and cell uptake of glycosylated porphyrins, phthalocyanines, and other dyes will be reported.  The per-fluorinated derivatives of these macrocycles facilitates appending  non-hydrolysable thio-sugars in one step and in high yield via nucleophilic aromatic substitution reactions.  Tuning of the photo physical properties is achieve by choice of porphyrinoid dye, by exocyclic moieties, and by the nature of the chelated metal ion.  The photophysical properties, in turn, determine the potential applications as diagnostics, imaging agents, and as therapeutics.  The number of sugars, the amphipathicity, and the degree of aggregation are properties that effect cell uptake. One advantage of several of the reported systems is that they do not readily bleach, therefore can be more effective in these applications. These systems serve as core platforms for the development of multifunctional materials for biomedical applications in that almost any primary nucleophile can be used as a reagent.

Glycosylated porphyrins, phthalocyanines, and related systems for therapies, diagnostics, and imaging

244th National Meeting (2012)

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