Synthesis, characterization, antioxidant activity, docking and simulation of potential anticancer agents of azo dye for pyridyl and its palladium(II) complex

Abstract

Herein, we describe the preparation and characterization of a novel azo dye of pyridyl, namely, (E)-N-(4-hydroxy-3-(pyridin-3-yldiazenyl)phenyl)acetamide (EHPYPA) and its palladium(II) complex. The palladium(II) complex bears the formulation [Pd(EHPYPA)Cl], which is reported by electrospray ionization mass spectrometry, CHN analysis, FT-IR, UV–Vis, ¹HNMR spectroscopies, molecular docking and simulation. The synthesis and structural properties of the azo dye and its palladium(II) complex are reported. The EHPYPA ligand showed important changes in the colours and spectra at different values of acidity, which permit to use of it as an indicator in analytical chemistry. The EHPYPA ligand behaves as N,O-bidentate donor ligand forming chelates. The ligand and palladium complex have been screened against the SKOV-3 cell line using the MTT method. Furthermore, the docking results indicate favourable docking with scores were -7.3 kcal/mol, -7.8 kcal/mol, and        -11.2 kcal/mol for the ligand, palladium complex and Co-crystal. RMSD values for the prepared compounds indicate stability while PSA, MolSA and SASA values indicate favorable drug-like potentials for the ligands. The palladium complex has been investigated as an anticancer agent where the activity data had shown that the palladium metal complex has to be a more potent anticancer than the parent azo ligand, suggesting that metalation increases the anticancer activity of the azo ligand of pyridyl.

KEY WORDS: Cell line, Palladium, Azo, Complex, Indicator, Molecular docking

Bull. Chem. Soc. Ethiop. 2025, 39(2), 287-300.                                                              

DOI: https://dx.doi.org/10.4314/bcse.v39i2.8