Synthesis of Novel Meso-Tetraphenyltetrabenzoporphyrins and Evaluation of Their Photodynamic Anticancer Activities.

To discover a potential anticancer photosensitizer drug, a series of meso-tetraphenyltetrabenzoporphyrins (m-Ph₄TBPs) with four carboxyl groups were afforded through a multistep reaction starting from cyclohexene. These new m-Ph₄TBPs demonstrated favorable antiaggregation properties and exhibited obvious absorption in the phototherapeutic window (600-800 nm). Additionally, m-Ph₄TBPs 1-5 displayed notable reactive oxygen species generation ability and obvious photodamage effectiveness against Eca-109 cells. Furthermore, m-Ph₄TBP 4 was able to inhibit tumor growth in mice bearing Eca-109 cells and demonstrated superior biosafety toward the kidney and liver both in vitro and in vivo. These results indicated that compound 4 could be considered a promising candidate for further studies in photodynamic therapy.