Study on synthesis, characterization and biological activity of some new nitrogen heterocycle porphyrins

Abstract

Seven new nitrogen heterocycle porphyrins, 5,10,15,20-tetra[4-( N-pyrrolidinyl)phenyl]porphine (TBPPH 2), 5,10,15,20-tetra[4-(4′-ethylpiperazinyl)phenyl]porphine (TEPPH 2), 5,10,15,20-tetra [4-(4′-butylpiperazinyl)phenyl]porphine (TUPPH 2), 5,10,15,20-tetra[4-(4′-heptylpiperazinyl) phenyl]porphine (THPPH 2), 5-[4-(4′-ethylpiperazinyl)phenyl]-10,15,20-triphenylporphine (MEPPH 2), 5-[4-(4′-buthylpiperazinyl)phenyl]-10,15,20-triphenylporphine (MUPPH 2) and piperazine bridge porphine dimer N, N′-di(5,10,15,20-tetraphenylporphinato)piperazine (DiPPH 2) have been synthesized by the direct condensation of nitrogen heterocycle substituted benzaldehydes with pyrrole. Each porphine bears one or four substituted pyrrolidine or piperazine moieties that have been used as drugs. Their structures were characterized by elementary analysis, MS, 1H NMR, IR and UV–vis. These nitrogen heterocycle porphyrins aggregates in water and THF solution were studied by the spectrophotofluorimetry. The anticancer activity of these porphines for the liver cancer cells, the stomach tumor cells and the nasopharyngeal carcinoma cancer cells were tested by the MTT assay. Compared with cis-platinum ( cis-Pt) and 5-Fluorouracil (5-Fu), the nitrogen heterocycle porphyrins have the better biological activity and might have potential application in medicine.