Synthesis, spectroscopic characterization, X-ray structure and biological screenings of organotin(IV) 3-[(3,5-dichlorophenylamido)]propanoates

Six new organotin(IV) complexes with general formula R3SnL/R2SnL2 where R = CH3 (1, 4), n-C4H9 (2, 5), C6H5 (3) or C8H17 (6) and L = 3-[(3,5-dichlorophenylamido)]propanoic acid were synthesized and structurally characterized by elemental analyses, FT-IR, NMR (1H and 13C) spectral studies, and mass spectrometry. Spectroscopic results suggest that the ligand coordinate through oxygen atom of the carboxylate groups. Crystal structure of complex (2) exhibits distorted trigonal-bipyrimidal geometry around the tin atom while that of complex (3) exhibits tetrahedral geometry around the tin atom. Complexes (1–6) were screened for their antifungal and antibacterial studies and the results showed that the triorganotin(IV) complexes have higher activity against these microbes than the diorganotin(IV) complexes. The complexes bind to DNA via electrostatic interaction of Sn(IV)+ moiety with the negatively charged oxygen of phosphate group of DNA resulting in hyperchromism.

The synthesized compounds interact with DNA via intercalative mode of interaction in which the compounds insert itself into the base pair of DNA.Figure optionsDownload as PowerPoint slideHighlights
► Synthesis of di/tri-organotin(IV) of 3-[(3′,5′-dimethylphenylamido)]propanoic acid.
► Interaction with SS-DNA via electrostatic mode.
► Antimicrobial activity.