比率型过氧化氢荧光探针的合成及成像应用  

Synthesis and imaging application of ratiometric fluorescent probe for hydrogen peroxide

作　　者：胡伟 王旭梅 柴丽 翟浩 宋新建 HU Wei;WANG Xumei;CHAI Li;ZHAI Hao;SONG Xinjian(Department of Chemistry,Xinzhou Normal University,Xinzhou 034000,Shanxi,China;Hubei Key Laboratory of Biological Resources Protection and Utilization,Hubei Minzu University,Enshi 445000,Hubei,China;Shanxi Weijian Medical Technology Co.,Ltd.,Xinzhou 034000,Shanxi,China)

机构地区：[1]忻州师范学院化学系,山西忻州034000 [2]湖北民族大学生物资源保护与利用湖北省重点实验室,湖北恩施445000 [3]山西惟健医疗科技有限公司,山西忻州034000

出　　处：《精细化工》2023年第11期2421-2429,共9页Fine Chemicals

基　　金：国家自然科学基金项目(22166017)。

摘　　要：以6-甲氧基苯并噻唑-2-羟基喹啉为双光子荧光团、硼酸酯为过氧化氢(H_(2)O_(2))识别基团,合成了比率型检测H_(2)O_(2)的双光子荧光探针{6-甲氧基-2-[6-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷-2-基)喹啉-2-基]苯并[d]噻唑}(MQH_(2)O_(2))。利用^(1)HNMR、^(13)CNMR、HRMS确定了其结构,利用荧光光谱和双光子荧光光谱对探针MQH_(2)O_(2)进行了H_(2)O_(2)响应能力的评估。结果表明,探针MQH_(2)O_(2)具有良好的H_(2)O_(2)比率[30 min内比率(I_(535)/I_(465),其中,I_(535)和I_(465)分别为波长为_(535)和_(465)nm处的荧光强度)响应信号比未加H_(2)O_(2)增强约25.4倍、检出限低至38.6nmol/L]和双光子性质(最大双光子荧光活性截面为150 GM)。通过双光子共聚焦成像完成了细胞和大脑组织成像。该探针能够实现脑卒中诱导细胞氧化应激的原位成像分析。Two-photon fluorescence probe,6-methoxy-2-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-yl]benzo[d]thiazole(MQH_(2)O_(2)),was synthesized from 6-methoxybenzothiazol-2-hydroxyquinoline as fluorescence moiety and borate ester as hydrogen peroxide(H_(2)O_(2))recognition moiety,and characterized by ^(1)HNMR,^(13)CNMR and HRMS.The response sensitivity of MQH_(2)O_(2) to H_(2)O_(2) was evaluated by fluorescence spectroscopy and two-photon fluorescence spectroscopy.The results revealed that the probe MQH_(2)O_(2) displayed good H_(2)O_(2) ratio[(I_(535)/I_(465),herein,I_(535) and I_(465) are fluorescence intensity at wavelength _(535) and _(465) nm,respectively)response enhancement of about 25.4-fold than that within 30 min and detection limit as low as 38.6 nmol/L]and proficient two-photon properties,with a maximum two-photon fluorescence active cross-section of 150 GM.Finally,data from cell and brain tissue analysis conducted by two-photon confocal imaging proved that the probe was capable of accomplishing in situ imaging analysis of oxidative stress caused by stroke.

关 键 词：比率型荧光探针 过氧化氢 双光子激光共聚焦成像 脑卒中 氧化应激 功能材料 

分 类 号：O657.3[理学—分析化学] R313[理学—化学]