Efficient Synthesis of Peptide Conjugated Perylene Diimide Bola-Amphiphile using 2-Chlorotrityl Chloride Resin and its Application to Photodynamic Therapy

Abstract

Perylene-3,4,9,10-tetra carboxylic diimide (PDI) has remarkable features as a photosensitizer in Photodynamic Therapy. However, PDIs poor solubility in aqueous condition limits its use. So it is commonly functionalized by various substituents on imide positions where two nitrogen groups comprised with imide moiety. However, there has been a technical limitation to conjugate them with proper amine gorups such as amino acids or peptides having pi-electron system. To overcome this problem, solid-phase peptide synthesis (SPPS) method has been utilized to conjugate peptides having diverse pi-electron functional molecules. But still other problems appeared such as low yield with harsh reaction condition. Therefore, a new method was designed to overcome such disadvantages of conventional SPPS method. For this, reaction times, loading level, and solvent system were optimized. In this research, RGD sequence was conjugated as a substituent on imide position. The RGD sequence is well known as a cell attachment component. Thus, we could develope very useful materials which has both strong cell adhesion ability and photosensitizer for photodynamic therapy.