Construction and Characterization of Azo-Metal Chelates Based on the Prepared 5-((4-aminophenyl)diazenyl)pyrimidine-2,4,6(1H,3H,5H)-trione Ligand as Antimicrobial and Anticancer Agents Against Hepatocellular Carcinoma
摘要
Azo-metal chelates have attracted increasing attention due to their notable biological activities, including antimicrobial and anticancer effects, driven by their ability to interact with cellular targets through metal coordination. In this study, a novel azo ligand based on barbituric acid and p-phenylenediamine was synthesized and reacted with various metal ions—Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Fe(III), and Ag(I)—to form stable metal chelates. The synthesized compounds were structurally characterized using elemental analysis, FT-IR, UV–Vis, ¹H NMR, mass spectrometry, thermal analysis (TG/DTG), magnetic susceptibility, and XRD. Spectroscopic data confirmed that coordination was ocurred through azo- nitrogen and carbonyl -oxygen atoms, and most chelates exhibited either tetrahedral or octahedral geometry with nanoscale crystallinity and high thermal stability. Biological assays revealed a significant enhancement in both anticancer and antimicrobial activities for the metal chelates compared to the free ligand. The Ag(I) complex displayed the most potent cytotoxic effect against Hep-G2 liver cancer cells, with an IC₅₀ of 14 µg/mL compared to 80 µg/mL for the ligand. Additionally, molecular docking studies demonstrated strong interactions of selected chelates—particularly Fe(III) and Cu(II)—with the FGFR4 kinase domain, supporting their potential therapeutic value. These findings suggest that such metal–azo systems could serve as promising scaffolds for future drug development in the fields of cancer and infectious disease treatment.