Synthesis, characterization, preliminary biological screening, and interaction studies of the bis(pyridinium)amine compound, 4,4'-[(2-aminophenyl)azanediyl]bis(1-methylpyridin-1-ium)triflate with biological macromolecules

Abstract

Bis(pyridinium)amine 4,4'-[(2-aminophenyl)azanediyl]bis(1-methylpyridin-1-ium)triflate ([H₂L][TfO]₂) was synthesized and characterized by elemental analysis, UV–Vis, fluorescence, FT-IR, ¹H, and ¹³C NMR spectroscopies, mass spectrometry, and a single crystal X-ray structure analysis. The potential of the title compound to interact with calf thymus DNA (CT-DNA) and bovine serum albumin (BSA) was investigated with the help of UV–Vis, florescence and docking studies. UV–Vis spectroscopy indicated that the binding of [H₂L][TfO]₂ with CT–DNA took place via a groove binding mode. [H₂L][TfO]₂–BSA was characterized by moderate binding constant, electrostatic interaction and spontaneous association. [H₂L][TfO]₂ Displayed excellent enzyme inhibition activity with Trypsin and acetylcholine esterase. [H₂L][TfO]₂ was found to be an efficient antioxidant, scavenging the radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) in a dose dependent manner. [H₂L][TfO]₂ exhibited activity against six microbes selected for the study.