Synthesis of 4-((4-(4-nitrophenoxy)phenyl)diazenyl)benzene-1,3-benzoate:Experimental, DFT and, DNA binding investigation through spectral and molecular docking studies

Pharmacists and other researchers have always been fascinated by the DNA sensing evaluation. This piece of work emphasizes on the synthesis, characterization and DNA sensing of a novel azo ester (N = N, -COO) molecule. The product (1A) was synthesized employing a typical esterification reaction between previously reported resorcinol coupled azo dye and Benzoyl chloride. The structural interpretation of the synthesized ester was done by FT-IR (Fourier transform infrared), NMR (Nuclear magnetic resonance), UV/VIS (ultraviolet–visible spectroscopy), and single crystal X-ray diffraction studies. XRD analysis elucidated the Ester 1A to be in the Monoclinic system with P21/n space group. The DFT simulation experiments were also examined to investigate the structural implications of the resulting product. The higher softness (S), electrophilicity index (ω) and electronegativity (χ) values demonstrated greater polarizability and reactive nature of the compound. Further, wet and silico binding methods were employed to examine the DNA sensing ability of the synthesized molecule with SS-DNA. UV/VIS spectroscopy and hydrodynamic measurements (Viscosity) suggested Groove binding mode of interaction with a moderate value of binding constant, which was further confirmed by molecular docking techniques.