Cellular internalization, cytotoxicity and DNA binding property of 2,3-diaminophenazine, synthesized using Jeanbandyite, a heterogeneous catalyst

Abstract

In recent years, the development of novel chemistry routes for the synthesis of organic compounds has attracted special attention. 2,3-Diaminophenazine (DAP), a derivative of Phenazine, is a large group of nitrogen-containing heterocyclic compound with diverse chemical structure and various biological activities, such as antibacterial, antimicrobial, anti-inflammatory, and anticancer activities. Phenazine is a fluorescent molecule with wide range of biological properties. Therefore, a novel chemical methodology is required for effective synthesis of this product. Numerous oxidants can easily oxidize ortho-phenylenediamine (OPD) to create luminous DAP. This article discusses a simple, sustainable, and safe way to synthesize DAP using water as a green solvent and Jeanbandyite as a catalyst. Mass spectrometry, ¹H-NMR and ¹³C-NMR were used to characterize the molecule, and the catalytic efficacy of Jeanbandyite was assessed. The cellular uptake and cytotoxicity of DAP were investigated to determine whether DAP can be used as a bioprobe in bioapplications. Finally, DAP binding to DNA was methodically performed and confirmed using molecular docking.

Keywords: Catalysis; Cellular internalization; Green chemistry; Jeanbandyite; Phenazine.