Construction of a novel far-red fluorescence light-up probe for visualizing

intracellular peroxynitrite

Wangbo Qua,1, Changhe Niuc,1, Xiaoyu Zhanga, Wei Chend, Fabiao Yu【于法标】b, Heng Liua【刘恒】,b,d,⁎, Xiuhua Zhanga, Shengfu Wanga

a Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules & College of Chemistry and Chemical Engineering, Hubei University, Wuhan 430062, PR China

b Institute of Functional Materials and Molecular Imaging, College of Clinical Medicine, Key Laboratory of Hainan Trauma and Disaster Rescue, College of Emergency and Trauma, Hainan Medical University, Haikou 571199, PR China

c Wuhan Children's Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430016, PR China

d Department of Chemistry, Washington State University, Pullman, WA 99164, United States

Peroxynitrite (ONOO-) is an important reactive oxygen species (ROS), which can react with a variety of biologically active species and cause many diseases, such as cancer, neurodegenerative disorders. Herein, we develop a novel far-red fluorescent probe DCM-KA, which is equipping with α-ketoamide moiety caged DCM-NH2. The probe exhibits fluorescence off-on response to ONOO- over other biological interfering analytes by ONOO--induced α-ketoamide deprotection reaction. More importantly, the probe is biocompatible and has been successfully utilized to visualize endogenous ONOO- production in macrophage cell line J774A.1.

https://linkinghub.elsevier.com/retrieve/pii/S0039914019300645

Scheme 1. (a) Synthetic route of DCM-KA. (b) Proposed sensing mechanism of DCM-KA toward ONOO-.