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

Abstract

AbstractWater‐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 withβ‐cyclodextrin. Herein, we synthesized two novel zinc phthalocyanine derivatives connected toβ‐cyclodextrin moieties through covalent Schiff base linkage (TFP‐ZnPc/AβCD). In this procedure, aldehyde substituted phthalocyanine and amino‐appendedβ‐cyclodextrins with different length amino side chains were used. The compounds were characterized using FT‐IR,1H NMR, MALDI‐TOF, and UV‐vis. The newly designed photosensitizers did not self‐assemble in water and generated significant singlet oxygenvia1,3‐DPBF (1,3‐diphenylisobenzofuran) bleaching. Simultaneously, longer amino side chains increase1O2production efficiency. The PDT activity of the new TFP‐ZnPc/AβCD complexes was then examined on human breast cancer (MDA‐MB‐231) and fibroblast cells.In vitroresults show that PDT is more effective against cancer cells than normal cells. The new TFP‐ZnPc/AβCD could be an effective PDT drug.