咔唑基近红外亚硫酸氢根荧光探针及其在水样和生物成像中的应用  

Carbazole-based Near-infrared Bisulfite Fluorescent Probe and Its Applications in Water Sample and Bioimaging

作　　者：周金涛 朱天翔 尚主业 张志强[1] 孟庆涛[1] ZHOU Jintao;ZHU Tianxiang;SHAG Zhuye;ZHANG Zhiqiang;MENG Qingtao(School of Chemical Engineering,University of Science and Technology Liaoning,Anshan 114051,China)

机构地区：[1]辽宁科技大学化学工程学院,辽宁鞍山114051

出　　处：《发光学报》2024年第12期2066-2073,共8页Chinese Journal of Luminescence

基　　金：辽宁科技大学省级重点实验室开放课题基金(2024KFKT-10)。

摘　　要：亚硫酸氢盐(HSO_(3)^(-))作为一种重要的食品添加剂,在日常生活中被广泛使用,但过量的使用和滥用会对生物和环境造成有害影响。同时,HSO_(3)^(-)作为体内信号分子(SO_(2))的衍生物,在正常生理活动中发挥着巨大的作用,但体内HSO_(3)^(-)的异常表达和过量摄入会导致一些疾病的发生。因此,对于体内和环境中HSO_(3)^(-)的特异性和敏感性检测和监测具有重要意义。为此本文选用N-乙基-咔唑作为电子供体基团,2-氧代-4-苯基-2,5-二氢-3-呋喃甲腈作为电子受体基团,通过羟醛缩合反应合成了具有D-π-A结构的近红外HSO_(3)^(-)荧光探针(CL)。探针CL识别HSO_(3)^(-)后其近红外荧光下降且波长发生蓝移。通过高分辨质谱(HR-MS)和理论计算验证了探针CL对HSO_(3)^(-)的亲核加成传感机制。探针CL具有近红外发射(λ_(em)=685 nm)、较大的Stokes位移(195 nm)、良好的选择性以及高灵敏度(49 nmol/L)等优点。另外,探针CL已被制备成试纸,并与智能手机连用实现了水样中HSO_(3)^(-)的现场快速检测。最重要的是,该探针已成功应用于活鼠体内HSO_(3)^(-)的荧光成像。Bisulfite(HSO_(3)^(-))as an important food additive,is widely used in daily life.But excessive use and abuse can cause harmful effects on organisms and the environment.Concurrently,HSO_(3)^(-)as a derivative of the signal-ing molecule(SO_(2))in the body,plays a huge role in normal physiological activities.But the abnormal expression and excessive intake of HSO_(3)^(-)in the body can lead to a number of diseases.Therefore,it is of great significance to detect and monitor HSO_(3)^(-)in vivo and in the environment with the specificity and sensitivity.Herein,a near-infrared HSO_(3)^(-)fluorescent probe(CL)with D-π-A structure was synthesized by condensation reaction using N-ethylcarbazole as electron donor group and 2-oxo-4-phenyl-2,5-dihydro3-furanonitrile as electron acceptor group.The near-infrared fluorescence was declined and the wavelength was blue-shifted after the probe CL recognizes HSO_(3)^(-).The nucleophil-ic addition sensing mechanism of probe CL to HSO_(3)^(-)was verified by high resolution mass spectrometry(HR-MS)and theoretical calculation.The probe CL has the advantages of near-infrared emission(λ_(em)=685 nm),large Stokes shift(195 nm),high selectivity and sensitivity(49 nmol/L).In addition,probe CL has been prepared into a test paper and the on-site and rapid detection of HSO_(3)^(-)in water samples is realized by connection with smartphones.Most im-portantly,the probe has been successfully applied to fluorescence imaging of HSO_(3)^(-)in living mice.

关 键 词：亚硫酸氢盐 荧光探针 咔唑衍生物 环境水样 活体成像 

分 类 号：O482.31[理学—固体物理]