选择性识别果糖的二硼酸荧光探针的合成及初步活性研究

Synthesis and preliminary activity study of bisboronic acid fluorescent sensors for selective recognition of fructose

通过以2-(4-二羟基硼烷)苯基喹啉-4-羧酸(PBAQA)和羧酸苯硼酸作为功能单体,哌嗪作为连接片,在甲醇溶液中经过进行两次酰胺缩合,得到具有双结合位点的新型水溶性二硼酸化合物.初步的荧光活性实验证明,果糖能够显著性地增强化合物11,12的荧光强度,结合常数显著高于其他糖类.加入75 mmol·L^(-1)果糖后,荧光强度增加12倍.因此,化合物11,12适合用作果糖选择性识别和检测的荧光探针.本文合成具有双结合位点的新型二硼酸化合物水溶性好,这对寻找新型水溶性硼酸荧光探针,提高探针分子在食品和医药中对果糖识别能力具有重要意义.

Using 2-(4-dihydroxyborane)phenylquinoline-4-carboxylic acid(PBAQA)and carboxyl phenylboronic acid as functional monomers,and piperazine as a linker,two novel bisboronic acid compounds were obtained after two amide condensation reactions.Preliminary fluorescence binding studies showed that binding constants of these two sensors to fructose are higher than other sugars.Fluorescence intensity increased 12 fold after adding 75 mmol·L^-1 fructose.Therefore,compound 11,12 are promising fluorescent sensors to selectively recognize and detect fructose.It is worth mentioning that these two novel bisboronic acid compounds are well water-soluble.It is of great significance for developing novel water-soluble boronic acid fluorescent sensors and improving the ability of sensor molecules to recognize fructose in food and medicine.