A reversible coumarin-based sensor for intracellular monitoring cysteine level changes during Cu2+-induced redox imbalance

Abstract

Biological thiols are crucial small molecule amino acids widely existing in cells, which play indispensable roles in maintaining redox homeostasis of living systems. Owing to their abnormal levels have close relation with many diseases, thus, developing more convenient, rapid and practical in-vivo detection tools is imminent. Herein, a reversible coumarin-based probe (HNA) was successfully constructed through a simple two-step synthesis. HNA can detect Cys/Hcy with high response speed and desirable selectivity based on Michael addition recognition mechanism. Free HNA has an orange emission at 580 nm, but after addition of Cys/Hcy, the conjugated structure of probe HNA was destroyed by the attack of sulfhydryl, resulting in a new green emission at 507 nm. Further, HNA has been applied to monitor Cys/Hcy in HeLa cells and zebrafish. Notably, HNA has also been successfully applied for real-time tracing Cys levels changes in living cells and zebrafish during the imbalance in redox status caused by copper (II). This provides a new strategy for studying the process of oxidative stress in cells.