一种基于苯并噻唑衍生物的高选择性比率型高半胱氨酸荧光探针及生物成像  

A Benzothiazole-Based Ratiometric Fluorescent Probe for Highly Selective Detection of Homocysteine and Its Bioimaging Application

作　　者：申有名[1] 谷标 刘歆 唐裕才 李海涛[3] Shen Youming;Gu Biao;Liu Xin;Tang Yucai;Li Haitao(Hunan Provincial Key Laboratory of Water Treatment Functional Materials,Hunan University of Arts and Science,Changde,Hunan 415000;College of Chemistry and Materials Science,Hengyang Normal University,Hengyang,Hunan 421008;College of Chemistry and Chemical Engineering,Hunan Normal University,Changsha 410081)

机构地区：[1]湖南文理学院水处理功能材料湖南省重点实验室,湖南常德415000 [2]衡阳师范学院化学与材料工程学院,湖南衡阳421008 [3]湖南师范大学化学与化工学院,长沙410081

出　　处：《有机化学》2020年第8期2442-2449,共8页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21907026);湖南省自然科学基金(No.2019JJ50009);湖南省教育厅优秀青年基金(No.18B369);衡阳师范学院环境监测与评价中心(No.KYJG1803)资助项目.

摘　　要：高半胱氨酸(Hcy)被认为是血管和肾脏疾病的危险因素.因此,开发Hcy特异性荧光探针,特别是比率荧光探针具有重要的意义.基于邻羟基醛基化的苯并噻唑,合成了一种用于Hcy高选择性检测的比率荧光探针3-(苯并噻唑-2-基)-2-羟基-5-甲基苯甲醛(BA).相对于其他测试物种(包括半胱氨酸和谷胱甘肽),该探针BA对Hcy表现性出良好的选择性.探针BA自身显示出绿色荧光(544 nm),将Hcy加入到探针溶液中后,反应体系表现出蓝色荧光(478 nm).在0~1.0 mmol/L浓度范围内,荧光发射强度比值(I478 nm/I544 nm)与Hcy呈现良好的线性关系,检测限为1.6 mmol/L.该探针BA毒性低,渗透性好,能够用于细胞中的Hcy比率荧光成像,显示其在生物体系中潜在的应用.另外,通过核磁、质谱实验和密度泛函理论计算验证了探针对Hcy的识别机理.Elevated homocysteine(Hcy)has been considered as a risk factor for vascular and renal diseases.Therefore,the development of Hcy-specific fluorescent probes,especially ratiometric fluorescent probes is of great importance.In the present study,a highly Hcy selective ratiometric fluorescent probe 3-(benzo[d]thiazol-2-yl)-2-hydroxy-5-methyl-benzaldehyde(BA),based on an ortho-hydroxy aldehyde functionalized benzothiazole,is presented.The probe responded selectively to Hcy over other tested species including Cys and GSH with ratiometric fluorescence changes.The probe possessed itself green fluorescence(λem=544 nm).Addition of Hcy to the BA solution triggered remarkable blue fluorescence(λem=478 nm).The fluorescence intensity ratios(I478 nm/I544 nm)were linearly related to the amounts of Hcy from 0 to 1.0 mmol/L with a detection limit of 1.6μmol/L.The probe BA possessed low cytotoxicity and desirable cell permeability,and could be employed for the ratiometric imaging of Hcy in living cells,suggesting its potential applications in biological systems.Moreover,the sensing mechanism of BA for Hcy was verified by NMR,HRMS and time-dependent density function theory calculations.

关 键 词：高半胱氨酸 比率 荧光探针 细胞成像 

分 类 号：O657.3[理学—分析化学]