Design of a 1,8-naphthalimide-based OFF-ON type bioorthogonal reagent for fluorescent imaging in live cells  

作　　者：Zhuzhou Shao Chun Zhang Xiaohua Zhu Yajun Wang Wenyuan Xu Yu Chen Xiaoming Wang Hailiang Zhu Yong Liang 

机构地区：[1]State Key Laboratory of Coordination Chemistry,Jiangsu Key Laboratory of Advanced Organic Materials,School of Chemistry and Chemical Engineering,Nanjing University,Nanjing 210023,China [2]State Key Laboratory of Pharmaceutical Biotechnology,School of Life Sciences,Nanjing University,Nanjing 210023,China

出　　处：《Chinese Chemical Letters》2019年第12期2169-2172,共4页中国化学快报（英文版）

基　　金：financially supported by the National Natural Science Foundation of China (No.21803030);the National Thousand Young Talents Program;the Jiangsu Specially-Appointed Professor Plan;the NSF of Jiangsu Province (No.BK20170631) in China

摘　　要：A novel 1,8-naphthalimide-based OFF-ON type fluorogenic sydnone(Naph-Syd) is designed as bioorthogonal probe for imaging.Sydnone moiety efficiently quenches the native fluorescence of 1,8-naphthalimide,which can be restored with the enhancement of about 300-fold,after reacting with strained cyclooctynes to form pyrazole products(Naph-Pyr).The second-order rate constant of this bioorthogonal cycloaddition can be up to 2.5 L mol^-1s^-1,which benefits imaging of biomolecules at low concentrations in cellular environment.A novel 1,8-naphthalimide-based OFF-ON type fluorogenic sydnone（Naph-Syd） is designed as bioorthogonal probe for imaging.Sydnone moiety efficiently quenches the native fluorescence of 1,8-naphthalimide,which can be restored with the enhancement of about 300-fold,after reacting with strained cyclooctynes to form pyrazole products（Naph-Pyr）.The second-order rate constant of this bioorthogonal cycloaddition can be up to 2.5 L mol-1s-1,which benefits imaging of biomolecules at low concentrations in cellular environment.

关 键 词：Bioorthogonal cycloaddition 1 8-NAPHTHALIMIDE Photophysical property Sydnone Turn-on fluorescence 

分 类 号：Q-334[生物学] O657.3[理学—分析化学]