基于激发态分子内质子转移机制的3-羟基黄酮探针用于检测生物硫醇

3-Hydroxyflavone-Based Excited State Intramolecular Proton Transfer Probe for Detection of Biothiols

生物硫醇在细胞的新陈代谢、生长分化和氧化还原平衡过程中扮演着十分重要的作用。本文以4-二甲氨基苯甲醛为起始原料设计合成了一个新的“关-开”型荧光探针HF-DBS。该探针可被生物硫醇选择性地催化水解,生成具有强荧光发射的3-羟基黄酮荧光团(HF),HF特有的激发态分子内质子转移(ESIPT)性质使其具有较大的斯托克斯位移。该探针显示出高选择性、高灵敏度、良好的生物相容性和抗干扰能力,且在生理条件下响应良好,可成功应用于细胞内的生物硫醇检测和活细胞成像。另外,该探针能够做成试纸对半胱氨酸进行快速检测。

Biothiols play an important role in cell growth and differentiation,metabolism and redox balance.In this paper,a new“off-on”fluorescent probe,HF-DBS,was designed and synthesized from the starting material 4-dimethylaminobenzaldehyde.The probe can be selectively hydrolyzed by biothiols to produce the 3-hydroxyflavone fluorophore(HF)with strong fluorescence emission,which has the property of excited state intramolecular proton transfer(ESIPT)and therefore has a large Stokes shift.In addition,the probe has high selectivity,high sensitivity,good biocompatibility and anti-interference ability,it can be used under physiological conditions.Thus,this probe has been successfully applied to intracellular biothiols detection and live cell imaging.In addition,the probe can be made into test paper for rapid cysteine detection.