Evaluation of singlet oxygen generators of novel water-soluble perylene diimide photosensitizers

Abstract

In this study, novel photosensitizers using three water-soluble green perylene diimide (PDI)-based ligands were synthesized, which can be used as photosensitizing drugs in photodynamic cancer therapy (PDT). These three efficient singlet oxygen generators were prepared via reactions of three newly designed molecules, namely 1,7-di-3-morpholine propylamine-N,N '-(l-valine-t-butylester)-3,4:9,10-perylyne diimide, 1,7-dimorpholine-N,N '-(O-t-butyl-l-serine-t-butylester)-3,4:9,10-perylene diimide and 1,7-dimorpholine-N,N '-(l-alanine t-butylester)-3,4:9,10-perylene diimide. Although there have been numerous photosensitizers, most of them have a limited useable range of solvent conditions or low photostability. These sensitizers have demonstrated strong absorption and red-light excitation. The singlet oxygen production of the newly synthesized compounds was investigated using a chemical method with 1,3-diphenyl-iso-benzofuran as a trap molecule. In addition, they do not have any dark toxicity at the active concentrations. Owing to these remarkable properties, we demonstrate the singlet oxygen generation of these novel water-soluble green perylene diimide (PDI) photosensitizers with substituent groups at the 1 and 7 positions of the PDI material, which are promising for PDT.