Study On Silicon-containing Organotin Complexes With Anticancer Activity

In recent years,researchers have synthesized many organotin compounds with biological activity.In order to further study the effects of silicone alkyl groups and ligand on the biological activities of organotin compounds,in this paper,eight triorganotin acetoacetate amino acid complexes and 12 diorganotin salicylaldehyde derivatives complexes containing silicon were designed and synthesized,like the following.Firstly,the amino acids reacted with acetic anhydride to produce acetyl amino acid,and then reacted with triorganotin salicylaldehyde derivatives with silicon trialkyl tin oxide in toluene at a ratio of 1:2 to get triorganotin acetoacetic amino acid complexes.The diorganotin salicylaldehyde derivatives complexes first formed Schiff bases with o-aminophenol through salicylaldehyde or its derivatives,and then reacted with silicon dialkyl tin dichloride in the presence of sodium methanol at a ratio of 1:1 to produce the target complexes.The structure of the complex was shown below.R=H,CH3,Ph R=Me3SiCH3,Ph R1=Me3SiCH2,Ph,Cy R2=Me3SiCH2,Ph X=H,NO2,CH3,Cl,Br Y=H,OCH3The complexes were characterized by IR,1H NMR,13C NMR and elemental analysis,test results showed that the Sn atom in the organotin acetyl amino acid complex didn’t coordinate with the carbonyl oxygen in O=CO,so the central Sn atom may be tetra-coordinated.The Sn-O bond and Sn-N bond were formed in the organotin salicylaldehyde derivative complex,and the central Sn atom may be five-coordinated,in addition,the five-and six-member ring were formed by the central Sn atom,N atom of CH=N and O atoms of two phenolic hydroxyl groups.All of these synthesized compounds were given the results of the test of biological activity in vitro by use of Anti-human osteosarcoma cells 143B and human lung cancer cells H1229.The results showed that all the complexes had good inhibitory activity and certain selectivity to both cells.According to IC50,the complex labeled 7a showed the highest activity to 143B cells,and when the IC50 value was 0.136 μmol/L,the complex labeled 7b showed the highest activity to H1229 cells,when the the IC50 value was 0.132 μmol/L,test results of normal cells showed that the complexes labeled la and 3a were less toxic.When IC50 value was 0.1 pmol/L,the inhibition rates of 1a and 3a was 1.75%and 6.18%,respectively,while the inhibition rates of 3a on tumor cells at this concentration were 45.52%.