Synthesis, Structure And Properties Of Aromatic Phthalic Acid Organotin Compounds

Recent years, the application of organotin compounds extends continuously under the study of synthesis especially in property industry and agriculture as stabilizer, catalyst, stain-proof paint, insecticide, wood preservatives etc. It's worth pointing out that the organotin compounds have attracted people's attention and concern for the application in medicine and pharmacology in recent years. The study about the structure-function relationship between structural patterns and biological activity of organotin compounds is the one of hot area of research.Tellurium is located in the sixth group in the periodic and is the fourth most abundant trace element in the human body after iron, zinc, rubidium. Tellurium and its compounds have a broad application value in metallurgical, chemical, electrical and electronic, solar batteries, glass colorant, new infrared detection materials, semiconductor materials and other fields. Recent studies proved that the beneficial pleiotropic activities of organotellurium compounds have been described due to their pharmacological properties, such as anti-oxidative, anti-inflammatory, immune-modulatory activities, anti-tumor, anti-leukemia cell effect. Some tellurium-containing compounds have used in clinic treatment, and some have been in the clinic study, due to their low toxicity.In order to design and synthesize the novelty organotin compounds, we choose aryltelluronic acid with different substituent groups as ligand and react with alkyl tin choride, based on the synergy effects. So, we synthesized some new aryltelluronic organotin complexes and embarked on an investigation of these organotin devatives. The main work as follows:1. Fluorine-containing aryltelluronic acid(3-fluorobenzenetelluronic acid, 3,4-difluorobenzenetelluronic acid, 3,4,5-trifluorobenzenetelluronic acid, 3,5-difluorobenzenetelluronic acid, 3,5-bis(trifluoromethyl)benzenetelluronic acid) were synthesized, and their reactions with triorganotin chloride were researched. Ten organotin compounds were obtained through reaction. These compounds were characterized by used of the element analysis, IR and NMR. Nine of their crystals were gained. Results showed that(1) when the 3-fluorobenzenetelluronic acid, 3,4-difluorobenzenetelluronic acid, 3,4,5-trifluoro- benzenetelluronic acid react with triorganotin chloride respectively, the product are dimeric structure with four tin atoms core and Te2O2 four-membered-ring. Besides, one hydroxyl group in each tellurium atom was not involved in reaction. The central tellurium atoms are all six coordinational distorted octahedron configuration, while the tin atom in four coordinated tetrahedron structures.(2) When the 3,5-difluorobenzenetelluronic acid, 3,5-Bis(trifluoromethyl)benzenetelluronic acid react with triorganotin chloride respectively, the product is monomer structure with four tin atoms core. Part of these complexes shows one-dimensional chain or two-dimensional network supramolecular structure by intermolecular C-H???F or C-H???O interactions.2. 4-ethoxybenzenetelluronic acid, 4-Bromobenzenetelluronic acid and 2-methyl-pyridine-5-telluronic acid were synthesized, and their reactions with triorganotin chloride wree researched. Seven organotin compounds were obtained through reaction. The element analysis, these compounds were characterized by used of the element analysis, IR and NMR. Finally, we got five of their crystals. Results showed that the compounds obtained through the reaction of triorganotin chloride and arenetelluronic acids are dimeric structure with four tin atoms in the central. That is similar with the structures described above.3. Antitumor activities in vitro of part of new synthesized compounds were tested based on the analyses of structures of these, which show that the majority of these complexes showed significant antitumor activity against human lung a denocarcinma cell line(A549) and human cervical carcinoma cell line(Hela). We make a summing up of structure-activity relationship. For example, triphenyltin complexes show more effective activities against the tumor cells A549 and Hela than trimethyltin complexes.4. The interaction between aryltelluronic organotin esters with Calf Thymus DNA(CT-DNA) had been studied by fluorescence spectrometry. Experimental results showed that the fluorescence intensity of EB-DNA system decreased with increasing concentration of these complexes, and a dose-response phenomenon is observed, illustrated that these compounds could quench the fluorescence of DNA. From the Stern-Volmer plots of the fluorescence titration of the complexes with CT-DNA, the values of the quenching constant can be calculated. The strength of the interaction with DNA can be seen from its numerical size. From the linear relation, the interaction mode between complexes and CT-DNA can be defined as intercalative mode or more complicated interactions.5. The interaction between aryltelluronic organotin esters with bovine serum albumin(BSA) had been studied by fluorescence spectrometry. The analysis of the binding of these complexes to BSA is monitored by examining its fluorescence spectra. Experimental results showed that the intrinsic fluorescence of BSA was quenched by majority of these complexes. We studied the characteristics of the fluorescence quench spectroscopy between aryltelluronic organotin esters with BSA and the result is dynamic quenching. According to the Stern-Volmer equation, we calculate the quenching constants, the constant and the binding points, which show that strong binding between these complexes with BSA. The conformational and micro-environmental changes occured in BSA in the presence of aryltelluronic organotin esters had been studied by synchronous fluorescence spectra Results of synchronous fluorescence spectra show that the intensity of emission corresponding to tryptophan and the tyrosine obviously decrease, and the conformational and micro-environmental changes occur in BSA in the presence of aryltelluronic organotin esters.