Synthesis, Crystal Structures, and Cytotoxicity of Thiophene-2-carbaldehyde N(4)-Cyclohexylthiosemicarbazone and Its Diorganotin(IV) Complex

Abstract

Thiophene-2-carbaldehyde N(4)-cyclohexylthiosemicarbazone C₁₂H₁₇N₃S₂ (HL) and diorganotin(IV) complex [Ph₂Sn(L)Cl] (1) have been synthesized and characterized by elemental analysis, IR, and single-crystal X-ray diffraction. Complex 1 contains mononuclear neutral molecule composed of one five-coordinated diorganotin(IV) ion, one NS bidentate anionic thiosemicarbazone ligand, one chloridion, and two phenyl group, respectively. In vitro biological studies have indicated that coupling of HL with Ph₂Sn(IV) leads to an enhancement of the cytotoxicity of the free ligand. Importantly, complex 1 could distinguish the human liver hepatocellular carcinoma HepG-2 cells from normal hepatocyte QSG7701 cells.

Keywords:

• crystal structure
• cytotoxicity
• diorganotin(IV) complex
• thiosemicarbazone

Supplementary Materials

Crystallographic data for the structural analyses reported in this article have been deposited with the Cambridge Crystallographic Data Centre with CCDC 920560 and 920559, respectively. Copies of this information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (Fax: t44 1223 336033; E-mail: [email protected]).

Additional information

Funding

This work was supported by the National Natural Science Foundation of China (21071043) and the Natural Science Foundation of Henan Province (132300410146).