Synthesis of Novel Porphyrin Derivatives and Their Cytotoxic Activities against A431 Cells.

Three novel porphyrins, including two Schiff-bases porphyrins, 5,10,15-triphenyl-20-[4-(2-(4-formyl)phenoxy)ethoxy]phenyl porphyrin ( H₂Pp( 1)), 5,10,15-triphenyl-20-[4-(2-(4-hydroxyimino)phenoxy)ethoxy]phenyl porphyrin ( H₂Pp( 2)) and 5,10,15-triphenyl-20-[4-(2-(4- m-hydroxyanilinodeneformyl)phenoxy)ethoxy]phenyl porphyrin ( H₂Pp( 3)), as well as three metalloporphyrins ( CuPp ( 1a), ZnPp ( 1b), and CoPp ( 1c)) of porphyrin H₂Pp( 1) were synthesized. Their molecular structures were characterized by ¹H-NMR, MS, UV/VIS, and FT-IR spectra. Furthermore, they were evaluated by their cytotoxicities against human epidermal squamous cell carcinoma cell (A431) and normal human horn cells (HaCaT) in vitro with MTT assay. Interestingly, these porphyrins and metalloporphyrins, which had a negligible cytotoxicity to HaCaT cells, showed highly cytotoxicity against A431 cells with IC₅₀ values in the range of 6.6-9.8 μ M, and metalloporphyrins exhibited higher cytotoxicity than that of metal-free porphyrins. [ABSTRACT FROM AUTHOR]