Azo Dye Derivatives As Dual-Application Materials: Anti-Prostate Cancer And Nonlinear Optical Properties Investigation

Abstract

In this study, three azo dyes derived from 2-naphthol, 2-aminobenzoic acid, 3-aminobenzoic acid, and 4-aminobenzoic acid were prepared. They were designated 2A, 3A, and 4A, respectively. The prepared compounds were characterized spectroscopically using mass, FT-IR, ¹HNMR, and ¹³CNMR spectroscopy. Density functional theory (DFT) calculations via B3LYP/6-311++G(d,p) provided understanding of the electronic structures. The calculated energy gaps of the 2A-4A at 3.0901, 3.3760 and 3.2524 eV, respectively, show that the ortho carboxylic substituted azo dye (2A)  has lower energy gap. The potential activity of the prepared azo dyes as potential cancer inhibitors, particularly for prostate cancer, was also theoretically investigated using molecular docking against the 1GS4 protein receptor. Molecular docking simulation demonstrated good affinity of the prepared azo dyes at -8.4, -7.2 and -7.7 kcal/mol, respectively,  recant was associated with four hydrogen bonds in 2A. The cytotoxicity of the prepared azo dyes was then tested using the MTT assay against  human prostate cancer cell line LNCaP. The calculated IC50 values were (46.97 ± 0.02), (71.11 ±  1.15), and (64.61 ± 0.06) µg/mol for azo dyes 2A-4A, respectively after 24 h of incubation after applying the azo dyes 2A-4A. The results of molecular docking were compared with the efficacy and cytotoxicity results of the prepared compounds and showed good agreement. The nonlinear optical properties of the prepared azo dyes 2A–4A are investigated using the diffraction pattern (DPs) method with 473 nm laser beam. The nonlinear refractive index values for azo dyes 2A is found to be 3.205 × 10⁻⁷ cm²/W. These high NLRI values make azo dyes 2A promising candidates for use in optical devices.