Organotin(IV) 4-nitrophenylethanoates: Synthesis, structural characteristics and intercalative mode of interaction with DNA

Four new organotin(IV) carboxylates, [Bu2SnL2] (1), [Et2SnL2] (2), [Bu3SnL]n(3), [Me3SnL]n(4), where L = 4-nitrophenylethanoates, were synthesized and characterized by elemental analysis, FT-IR and multinuclear NMR (1H and 13C). Spectroscopic results authenticated the coordination of ligand to the organotin moiety via COO group while X-ray single crystal analysis revealed bidentate chelating mode of coordination of ligand in complex 2 and a bridging behavior in complexes 3 and 4. Cyclic voltammetric (CV) technique was used to evaluate the electrochemical, kinetic and thermodynamic parameters of complexes 1-4, interacting with DNA. The linearity of the plots between the peak current (I) and the square root of the scan rate (ν1/2) indicated the electrochemical processes to be diffusion controlled. The diffusion coefficients of the free (Df) and DNA bound forms (Db), standard rate constants (ks) and charge transfer coefficients (α) were determined by the application of Randle–Sevcik, Nicholson and Kochi equations. Furthermore, the binding constants evaluated from voltammetric data revealed the following increasing order of binding strength: 2 < 1 < 4 < 3. For 1 and 2, the activity against prostate cancer cell lines (PC-3) was found consistent with the order obtained from voltammetric behavior.

Graphical abstractFour novel Organotin(IV) complexes of 4-Nitrophenyl ethanoic acid have been synthesized, and characterized by elemental analysis FT-IR, multinuclear NMR (1H, 13C) and X-ray single crystal analysis. Cyclic voltammetric technique was used to evaluate the electrochemical, kinetic and thermodynamic parameters of these complexes interacting with DNA.Figure optionsDownload full-size imageDownload as PowerPoint slide