Synthesis, structural characterization and cytotoxicity of a new proton transfer compound based on 2,4-diamino-1,3,5-triazine: an experimental and computational study

Abstract

In the present study, a new water-soluble proton transfer cytotoxic compound (dpp)(dapt).H₂O (Dx) (where dpp = diphenylphosphinate and dapt = 2,6-diamino-4-phenyl-1,3,5-triazin-1-ium) was synthesized and characterized by IR and NMR spectroscopy. Its crystal structure was determined, and the non-covalent interactions responsible for extending its supramolecular network were characterized. Density functional theory (DFT) and natural bond orbital (NBO) calculations were used to analyze the non-covalent interactions in Dx. The main non-covalent intermolecular interactions were also studied by Hirshfeld surface analysis and fingerprint plots. Finally, the anticancer and growth inhibitory activities of the synthesized proton transfer compound were investigated against human breast cancer cell line MDA-MB-231 after an incubation time of 24 and 48 hours using MTT assay. The in vitro result showed a time- and dose-dependent cytotoxic effect of Dx in cells. This result was supported by a molecular docking study where a binding energy value of −13.76 kcal mol⁻¹ clearly indicated the high affinity of Dx for interaction with DNA.