A <scp>Bioorthogonal‐Activated</scp> Fluorescence <scp>Turn‐On</scp> Probe Based on <scp>Nitrone‐Modified</scp> 1,<scp>8‐Naphthalimide</scp> for <scp>Live‐Cell</scp> Imaging
Yu Teng, Hong Yang, Xiang Li, Yongcheng Wang, Dali Yin, Yulin Tian
Abstract
Comprehensive Summary A nitrone‐modified 1,8‐naphthalimide was designed as a novel bioorthogonal‐activated turn‐on probe based on strain‐promoted alkyne‐nitrone cycloaddition (SPANC). The bioorthogonal cycloadducts were subsequently transformed into fluorescent rearrangement products by photo‐acceleration, which exhibited significant fluorescence enhancement, large stokes shift, and high fluorescence quantum yield. DFT calculations were performed to elucidate the fluorescence OFF‐ON mechanism. This fluorogenic strategy was successfully applied to labeling of proteins and visualizing mitochondria in live cells in real time.
Topics & Concepts
Bioorthogonal chemistryChemistryFluorescenceCombinatorial chemistryClick chemistryQuantum mechanicsPhysicsClick Chemistry and ApplicationsAdvanced biosensing and bioanalysis techniques