喹啉酮荧光探针的合成及性能研究

通过乙酰乙酸乙酯与间苯二胺反应制得4-甲基-7-氨基-2-喹啉酮(3),进一步与氨三乙酸反应制得新的喹啉酮酰胺衍生物5,其结构经红外、核磁氢谱、质谱等表征。5与La(NO3)3配位得到新的配合物6。元素分析、红外、质谱、热重-差热分析和摩尔电导等确定配合物6的分子式为La(C16H15N3O6)NO3]·4H2O。荧光测试表明,化合物5与稀土金属La配位后,荧光发光强度明显增加,荧光区间变窄。此外,化合物5与不同浓度鲱鱼精DNA作用的荧光变化情况表明:化合物5与鲱鱼精DNA有较强的相互作用,荧光光谱变化明显;鲱鱼精DNA对化合物5有荧光增强作用,DNA浓度为4.02×10-6mol/L时,增幅最大可达40%。实验结果表明,化合物5在DNA检测或疾病防治等方面有潜在的应用价值。

Studies on the Synthesis and Properties of Quinolinone-based Fluorescent Probe

7-Amino-4-methyl-2(1H)-quinolinone was synthesized by the reaction of m-phenylenediamine with ethyl acetoacetate (3), which was further reacted with nitrilotriacetic acid and produced a new amide compound 5. The chemical structure of compound 5 was characterized by IR, 1H NMR, and MS analyses. Coordination of compound 5 with La(NO₃)₃ produced a new La complex 6 with a molecular formula of ［La(C₁₆H₁₅N₃ O₆)NO₃］·4H₂O, which was analyzed by IR, MS, TG-DTA, elemental analysis, and molar conductivity. The result of fluorescence analysis showed that the La complex had a stronger fluorescence and narrower frequency-domain. The interaction of compound 5 with herring DNA solution was also studied by fluorescent spectroscopy at different concentrations. An obvious change of the fluorescent spectroscopy was observed, showing that there is a strong interaction between the DNA and compound 5. Addition of herring DNA could effectively enhance the luminescence intensity, and an intensity increased to 40% was observed at a DNA concentration of 4.02×10^-6 mol/L. Therefore, compound 5 has potential applications in DNA analysis and/or prevention and treatment of diseases.