具有生物活性的芳基咪唑并邻菲啰啉衍生物的合成及用作pH荧光传感探针

Synthesis of Bioactive Aryl Imidazole Derivatives and Their Applications for the pH-Induced Luminescence Sensing Probe

以1,10-邻菲啰啉为基本骨架设计合成了6种咪唑[4,5-f][1,10]邻菲啰啉的衍生物(3a^3f);研究了目标化合物对蛋白酪氨酸磷酸酶1B(PTP1B)的抑制作用,其最高抑制率可达(84.56±1.78)%,是潜在的PTP1B的抑制剂药物;基于1,10-邻菲啰啉优良的光学性能,通过荧光测试研究了不同pH对化合物3a^3f的影响,探讨了化合物在Britton-Robison(B-R)缓冲溶液中的质子化和去质子化现象;以硫酸奎宁为参比,计算了相应的荧光量子产率.结果表明,目标化合物均有较高的荧光量子产率,最高可达0.53.

Six kinds of imidazo[4,5-f][1,10]phenanthroline derivatives（3a-3f） were designed and synthe-sized based on [1,10]phenanthroline skeleton. The inhibition of the target compounds on PTP1B was studied and the highest inhibition rate could be up to （ 84.56＆#177;1.78 ）%. The results indicated that the target com-pounds could be used as the potential PTP1 B inhibitors and provide important therapy reference for the modernII diabetes and obesity. Owing to the excellent optical performance of 1,10-phenanthroline, the effects of pH on the luminescence properties of the target products（3a-3f） were also studied and the phenomenon of the protonation and deprotonation in the B-R buffer solution were explored. Taking quinine bisulphate as a refe-rence, the highest luminescence quantum yield of compounds 3 was 0.53. With the increase in pH value, the luminescence intensity of compounds 3 increased. In the range of pH=6-8, compounds 3 gave a strong and steady luminescence. However, the luminescence intensity of compounds 3 reduced when pH value was higher than 8. As a result, compounds 3 could be used as pH luminescence sensing probe.