Novel organotin complexes derived from 2,2′-selenodiacetic acid: synthesis and biological evaluation

摘要

The reactions of 2,2′-selenodiacetic acid and the corresponding organotin( IV ) chloride with sodium ethoxide in ethanol, or via a solvothermal synthetic route, have afforded four organotin polymers, namely, [(Me _(3) Sn) _(2) Se(CH _(2) COO) _(2) ] _( n ) ( 1 ), [(Me _(2) Sn) _(2) Se(CH _(2) COO) _(2) (μ _(3) -O)] _( n ) ( 2 ), [(Bu _(3) Sn) _(2) Se(CH _(2) COO) _(2) ] _( n ) ( 3 ), and [(Bu _(2) Sn)Se(CH _(2) COO) _(2) ] _( n ) ( 4 ). All the complexes were fully characterized by elemental analysis, FT-IR, NMR ( ~(1) H, ~(13) C, and ~(119) Sn) spectroscopy and single crystal X-ray diffraction analysis. The structural analysis reveals that complex 1 is a 2D-polymer containing interconnected 24-membered (Sn _(4) O _(8) C _(10) Se _(2) ) macrocyclic rings. Unlike complex 1 , the 2D polymer structure of complex 2 is made up of the typical ladder tetraorganodistannoxane unit containing 32-membered (Sn _(4) O _(8) C _(16) Se _(4) ) macrocyclic rings. Complex 3 is a 3D corrugated polymeric structure in which the deprotonated dicarboxylic acid acts as a tetradentate ligand by four oxygen atoms. Complex 4 is a 1D zigzag coordination polymer and the tin coordination geometry is described as skewed-trapezoidal bipyramidal. In particular, preliminary cytotoxic assessments of the involvement of complex 4 in the apoptotic death of MDA cells were conducted, and the results revealed that the antiproliferative and proapoptotic effect of complex 4 in MDA cells prominently contributed to the overload of intracellular ROS levels and the dysfunctional depolarization of mitochondrial membranes.