Synthesis biological screening and molecular docking studies of some tin (IV) Schiff base adducts

J Photochem Photobiol B. 2016 Nov:164:65-72. doi: 10.1016/j.jphotobiol.2016.09.018. Epub 2016 Sep 13.

Abstract

The search for an alternative to platinum anticancer agents is a major motivation for continuing investigations concerning the antitumor properties of other transition metal-based compounds. Keeping this in view, synthesis, antitumor and antimicrobial activity of diorganotin (IV) complexes was studied. A novel series of diorganotin (IV) complexes of the Schiff base ligand derived from 7-methoxy-2-hydroxy-1-naphthaldehyde, 1,2-phenylenediamine, Salicylaldehyde were synthesized. Physical and spectral examination was done through various techniques using elemental analyses, IR, 1H, 13C, 119Sn NMR, and 119mSn Mössbauer techniques respectively. The results obtained are in good agreement with 1:1:1 stoichiometry of Schiff base and 2:1 stoichiometry of the complexes. Octahedral geometry was assigned to all the synthesized complexes within six (6) coordination number around the tin. Antitumor activity was screened against human oral epidermoid carcinoma (KB) cell line. The diethyltin (IV) complex 2 showed the most promising cytotoxic results (IC50=0.35μM) against the cell line which is comparable with cisplatin (IC50=0.37μM). Docking studies revealed that these complexes can bind favorably within cisplatin binding site and the binding energy of complex 2 is more than that of cisplatin. Furthermore, binding of these complexes on human topoisomerase IIα enzyme and revealed that these complexes intercalating within the inter-strand of DNA showing interactions with DNA as well as protein that may results in DNA damage and cell death.

Keywords: Antitumor activity; Cisplatin; Organotin; Schiff base; Topoisomerases.

MeSH terms

  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Docking Simulation*
  • Schiff Bases / chemistry*
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Tin / chemistry*

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Schiff Bases
  • Tin