Synthesis, spectroscopic characterization and biological activities as an anticancer and antioxidant of the Pd(II) and Pt(IV) complexes with a new azo dye ligand derived from 5-methyl imidazole

Abstract

Pd(II) and Pt(IV) metal complexes with new heterocyclic azo dye as ligand 2′-[2′-(1-Hydroxy-4-methyl phenyl) azo]-5-methyl imidazole (HPA-5-MeI) were prepared by reacting a diazonium chloride salt solution of 2-amino-4-methyl phenol with 5-methyl imidazole in an alkaline ethanolic solution. Differing spectral techniques have been used to study the structures of the azo dye ligand (HPA-5-MeI) and chelate complexes such as elemental analysis (C.H.N), Mass spectrum, 1H-NMR, 13C-NMR, FT-IR, UV-Vis, XRD, thermal analysis (TGA/DTA), FE-SEM, and magnetic measurements. The molar conductivity indicates that the Pd(II) complex is not an electrolyte and does not contain conductive species, while the Pt(IV)-complex is the electrolyte because it contains chloride outside the coordination sphere. The results confirmed that the ligand (N, N, O) behaves as a tridentate and coordinates with the metal ion via the nitrogen atom of the azomethine group (C=N) of heterocyclic imidazole molecules, the nitrogen atom of the azo group (N=N), which is the farthest from the imidazole ring, and the oxygen atom of the phenolic ring. Antioxidant studies of synthesized compounds were also performed by measuring the DPPH radical scavenging assay. DPPH radical scavenging was used to measure the antioxidant activity and compare the produced compounds with ascorbic acid, a known antioxidant. However, MTT cytotoxicity assay was used to assess the anticancer and toxicity of ligand (HPA-5-MeI) and Pt(IV)-complex against breast cancer cell line (MCF-7). Furthermore, molecular docking studies have been conducted on the potent compounds that have several crucial interactions with (2XA0) proteins.