Synthesis and Antitumor Activity of Photosensitizer Eugenol Porphyrin Derivatives: A Combination Therapy of Chemotherapy and Photodynamic Therapy

Photodynamic therapy (PDT) is a promising treatment for cancer. At present, the development of photosensitizers has become a hot spot for research at home and abroad. In this study, 20 porphyrin-butylphenol compounds were synthesized, and the structures of the target compounds were analyzed by means of 1H NMR, IR, mass spectrometry, and other analytical methods. The quantum yield of the target compound as a photosensitizer for the production of singlet oxygen was determined by using a DPBF reactive oxygen probe (1,3-diphenylisobenzofuran). The anticancer activity of the synthesized target compounds was studied using HepG2 cells and A549 cells. The results of the singlet oxygen experiments showed that the Zn metal chelated compound had better singlet oxygen production than the free-base porphyrin. The cellular activity assays showed that the metal-chelated compounds exhibited better in vitro antitumor activity. This article mainly synthesized 20 porphyrin eugenol derivatives, which have certain anti-cancer activity against HepG2 and A549 cells, and the activity of metalloporphyrins is superior to that of non-metallic porphyrins.image