Hantzsch Ester Modified Asymmetric BODIPY Probe with Ultra-high Sensitivity for Ultra-fast Detection of Endogenous Hypochlorite in Living Cells  

作　　者：Tianli Zhu Mengting Zhao Rongcheng Wang Chenjun Dong Xuemei Dong Jie Sun Lixin Sun Chunchang Zhao 

机构地区：[1]Key Laboratory for Advanced Materials and Feringa Nobel Prize Scientist Joint Research Center,Institute of Fine Chemicals,School of Chemistry and Molecular Engineering,East China University of Science and Technology,Shanghai,200237 China

出　　处：《Chinese Journal of Chemistry》2023年第23期3319-3325,共7页中国化学（英文版）

基　　金：financial support by the National Natural Science Foundation of China(22077030,22271092,21977018,82173657,21874043);the China Post-doctoral Science Foundation(Grant No.2021M701196).

摘　　要：Hypochlorite(ClO^(-))is an important reactive oxygen species produced by the immune system to fight off invading pathogens,but its over-expression can interfere with normal physiological process and induce serious diseases.Although a variety of molecular probes have been reported for detecting ClO^(-),the development of advanced fluorescent tools with faster response and higher sensitivity to precisely monitor ClO^(-)remains a challenge.In this work,two Hantzsch ester(a derivative of 1,4-dihydropyridine)derived fluorescent probes MeDHP-BCl and MeDHP-PhBCl were constructed based on asymmetric BODIPY-matrix.These probes exhibit significant fluorescence turn-on in the ultra-sensitive(detection limit<1 nmol/L)and ultra-fast response(≤5 s)to ClO^(-).The reaction has been determined to be a highly selective N-chlorination of Hantzsch ester which cannot be activated by various common bioactive species,including nitric oxide(NO)that could oxidize Hantzsch ester under aerobic physiological conditions in most reports.MeDHP-PhBCl possessed a relatively longer fluorescence emission wavelength and higher quantum yield after activation,while more notably,MeDHP-BCl displayed lower cytotoxicity and more remarkable fluorescence increment in the response to ClO^(-),enabling selective and precise visualization of endogenous ClO^(-)over-expression in living RAW264.7 cells.

关 键 词：HYPOCHLORITE Hantzsch ester BODIPY Fluorescent probes Fluorescence spectroscopy Biomarkers Biosensors BIOIMAGING 

分 类 号：O62[理学—有机化学]