Photosensitizers for photodynamic therapy: One-pot heterogeneous catalytic transfer reduction of porphyrins

Abstract

A number of new porphyrin-based photosensitizers have been developed for Photodynamic Therapy (PDT) in recent years. Chlorins, which are a reduced form of porphyrins, show better potential of application since they have a stronger absorption band on the red region of the visible spectrum and, hence, a deeper penetration into tissues. We found that by using heterogeneous catalytic transfer reduction (CTR), meso-tetraphenylporphyrin (TPP) could be hydrogenated, although in modest yields, to meso-tetraphenylchlorin (TPC) in a single reaction step. Best reaction conditions were attained using formic acid or sodium phosphinate/water as hydrogen donors, tetrahydrofuran (THF) or toluene as solvent and 10% palladium on charcoal as catalyst.

Keywords

• Catalytic transfer reduction
• hydrogenation
• meso-tetraphenylchlorin
• meso-tetraphenylporphyrin
• photosensitizers