In VitroPhotodynamic Activities of Amphiphilic Phthalocyanine‐Amino Appendedβ‐Cyclodextrin Conjugates as Efficient Schiff Base Photosensitizer

Abstract Water‐soluble phthalocyanine has been considered as a potential photosensitizer for photodynamic therapy (PDT) applications. To achieve the best efficiency of phthalocyanine in PDT, amphiphilic zinc phthalocyanine was purposely designed and synthesized by conjugation with β ‐cyclodextrin. Herein, we synthesized two novel zinc phthalocyanine derivatives connected to β ‐cyclodextrin moieties through covalent Schiff base linkage (TFP‐ZnPc/A β CD). In this procedure, aldehyde substituted phthalocyanine and amino‐appended β ‐cyclodextrins with different length amino side chains were used. The compounds were characterized using FT‐IR, 1 H NMR, MALDI‐TOF, and UV‐vis. The newly designed photosensitizers did not self‐assemble in water and generated significant singlet oxygen via 1,3‐DPBF (1,3‐diphenylisobenzofuran) bleaching. Simultaneously, longer amino side chains increase 1 O 2 production efficiency. The PDT activity of the new TFP‐ZnPc/A β CD complexes was then examined on human breast cancer (MDA‐MB‐231) and fibroblast cells. In vitro results show that PDT is more effective against cancer cells than normal cells. The new TFP‐ZnPc/A β CD could be an effective PDT drug.