Synthesis, characterization, biological screenings and interaction with calf thymus DNA as well as electrochemical studies of adducts formed by azomethine [2-((3,5-dimethylphenylimino)methyl)phenol] and organotin(IV) chlorides

Novel azomethine adducts of Sn(IV) have been synthesized by the reaction of RnSnCl4−n (n = 1–3, R = CH3, n-C4H9, C6H5, C6H11) with 2-((3,5-dimethylphenylimino)methyl)phenol (HL). The products were characterized by elemental analysis, FT-IR, 1H, 13C and 119Sn NMR spectroscopy. Triphenyltin(IV) chloride [2-((3,5-dimethylphenylimino)methyl)phenol] (3) was also characterized by single crystal analysis. Spectroscopic and crystal data suggest that in all the complexes the ligand acts as a monodentate neutral molecule and is coordinated through oxygen to the tin atom forming pentacoordinated tin species. The phenolic hydrogen within the ligand is transferred to the imine nitrogen atom due to the coordination of oxygen with tin after complex formation. The ligand and its complexes have been screened for their biological activities, including DNA interaction, enzymatic, antibacterial, antifungal and cytotoxicity studies. Moreover, the electrochemical behavior of the synthesized compounds was also studied and the results obtained evidenced their irreversible oxidation.

Graphical abstractThe synthezed ligand and its organotin(IV) derivatives interact with CTDNA via intercalation mode of interaction and insert themselves into the base pairs of DNA. The compound-DNA complex is stabilised by π–π stacking.Figure optionsDownload full-size imageDownload as PowerPoint slide