Synthesis And Properties Of Fatty Acyl-Indigo Compounds

In the series of"Indigo"anti-cancer draug,Indirubin and its derivatives have plane or approximate plane struct and extensive conjuated system. They can be inserted bet- ween two base pair of DNA or RNA and take place the interaction, then wide range restrain many kinds of tumor. After research of QSAR of Indirubin and Indigo, we found Indigo have the necessary condition of insert into the interstice of Nucleic Acid molecule to combine with DNA or RNA.Then,the Indigo derivatives be Nitrogen substituted,will reduce the chance of engender the hydrogen bond, and will incress the chance of effect between the carbon-based oxygen atom and DNA.The molecule sturct of Indigo includes conjuated system, acquired the condition of engen- der the fluorescence.Through a mass of experiment, find the fatty acyl-Indigo compunds, not only have latency anti-cancer active but also novel small-molecule fluoresent compounds.This paper designed and synthesised nine fatty acyl-Indigo compounds. Through UV and FL spectra to ascertain their fluoresence properties, and choice some of the compounds for experiment exploration in vitro anti-cancer activity test and fluoresen- ce application. The main contents are as follows:Took glacial Acetic acid, Metacetonic acid, n-Butyric acid, Isobutyric acid, Cyclopropane Carboxylic acid and dichloro sulfoxide to prepare corresponding fat chloride. Then took these fat chloride and Indigo to synthesis five N-substituted fatty acyl-Indigo compounds.These compounds, structure be confirmed by IR,1HNMR, MS, HR-MS. Mensurated with UV and FL spectra we found these compounds have highly Stokes offset value. These indicated that these compounds are molecular compounds with fluorescence properties. Otherwise, through the experiments of vitro activity of cell-based screening, found these compounds have potential anti-cancer activity.Took fat chloride and Indigo as material to synthesis four N,N'-disubstituted fatty acyl-Indigo compounds.These compounds, structure be confirmed by IR,1HNMR, MS, HR-MS. Mensurated with UV and FL spectra we found these compounds have highly Stokes offset value. These indicated these compounds are small molecular compounds with fluorescence properties. Otherwise, through the experiments of vitro activity of cell-based screening, found these compounds have potential anti-cancer activity.We Chose some of the compounds as fluorescent probe.To mensurate CMC value of surfactant CTAB .Found the actual value is close to the CMC value which measured by us.