Encapsulation of glycosylated porphyrins in silica nanoparticles to enhance the efficacy of cancer photodynamic therapy

Encapsulation of glycosylated porphyrins in silica nanoparticles enhanced the efficacy of cancer photodynamic therapy compared with the free porphyrins.

Convenient Approach to Access Octa-Glycosylated Porphyrins via “Click Chemistry”

Easy, quantitative, and one-pot introduction of eight β-lactoside-modules onto a porphyrin-core was achieved through Cu+-catalyzed chemoselective coupling (click chemistry) between a porphyrin carrying eight alkyne-terminals and β-lactosyl azides. The obtained porphyrin-based glycocluster shows not only good water-solubility but also strong/specific lectin-affinity.

Synthesis of glycosylated cationic porphyrins as potential agents in photodynamic therapy

Trisalkylpyridinium porphyrins substituted by one glycosyl (glucosyl, maltosyl, and lactosyl) moiety have been prepared in acceptable yields. These glycosylated cationic porphyrins have been synthesized from pyrrole condensed with 4-pyridinecarboxaldehyde, and suitable ortho- or para peracetylglycosyloxybenzaldehyde derivatives in refluxing propionic acid –Ac2O followed by action of alkyliodide in DMF. Deprotection of the glycosylated moieties led to a new class of representative glycosylated porphyrins. Key words: porphyrins, cationic, glycosylated; phototherapy, cancer.