New azo-acridine derivatives as inhibitors of AGS cell line: Synthesis, coordination chemistry, cytotoxicity, and molecular modeling studies

Acridines are notable heterocyclic compounds characterized by three fused six-membered rings, contributing to a planar aromatic structure. This study focuses on synthesizing the ligand ۶,۶'-((۱E,۱'E)-acridine-۳,۶-diylbis(diazene-۲,۱-diyl))bis(۲,۴-dimethoxybenzoic acid) through key steps involving diazonium salt formation. The synthesis begins with dissolving ۳,۶-diamino acridine in hydrochloric acid and water, cooled to stabilize the diazonium salt. Sodium nitrite is added for diazotization, followed by ۲,۴-dimethoxybenzoic acid in an alkaline medium to yield the ligand, which is then purified. Metal complexes were formed by dissolving the ligand in ethanol and adding metal chloride salts such as PdCl₂, H₂PtCl۶.۶H۲O, and HAuCl۴⋅۴H۲O under controlled conditions suitable for various applications. They confirmed by thermal analysis, ۱H and ۱۳C-NMR, UV-Vis, FT-IR, mass, elemental analysis, atomic absorption, and molar conductance. X-ray diffraction and FESEM techniques were employed to analyze the crystallographic structure and surface morphology of the compounds, revealing significant differences among them. Molecular docking studies indicated that the Au(III) complex exhibits strong binding affinity with the RhoA protein, a potential target in gastric cancer therapy. The MTT assay was utilized to evaluate the cytotoxicity of ligand and Au(III)-Complex against human adenocarcinoma of the stomach (AGS) cells and normal line cells (Hs ۷۳۸.St/Int), highlighting their potential effectiveness in cancer treatment.

کلیدواژه ها:

۵JHH ، Acridine ، AGS cell line ، Cytotoxicity ، RhoA protein