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/AβCD). 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, 1H NMR, MALDITOF, 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 1O2 production efficiency. The PDT activity of the new TFP-ZnPc/AβCD complexes was then examined on human breast cancer (MDAMB- 231) and fibroblast cells. In vitro results show that PDT is more effective against cancer cells than normal cells. The new TFP-ZnPc/AβCD could be an effective PDT drug.
