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

Wangbo Qu; Changhe Niu; Xiaoyu Zhang; Wei Chen; Fabiao Yu; Heng Liu; Xiuhua Zhang; Shengfu Wang

doi:10.1016/j.talanta.2019.01.065

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

Talanta. 2019 May 15:197:431-435. doi: 10.1016/j.talanta.2019.01.065. Epub 2019 Jan 17.

Authors

Wangbo Qu¹, Changhe Niu², Xiaoyu Zhang¹, Wei Chen³, Fabiao Yu⁴, Heng Liu⁵, Xiuhua Zhang¹, Shengfu Wang¹

Affiliations

¹ 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.
² Wuhan Children's Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430016, PR China.
³ Department of Chemistry, Washington State University, Pullman, WA 99164, United States.
⁴ 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.
⁵ 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; 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; Department of Chemistry, Washington State University, Pullman, WA 99164, United States. Electronic address: liuheng11b@hubu.edu.cn.

PMID: 30771958
DOI: 10.1016/j.talanta.2019.01.065

Abstract

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.

Keywords: Dicyanomethylene benzopyran derivative; Far-red; Fluorescence off-on; Imaging endogenous peroxynitrite; Naked-eyes detection.

MeSH terms

Animals
Cells, Cultured
Fluorescence*
Fluorescent Dyes / chemical synthesis
Fluorescent Dyes / chemistry*
Mice
Molecular Structure
Optical Imaging
Peroxynitrous Acid / analysis*
RAW 264.7 Cells

Substances

Fluorescent Dyes
Peroxynitrous Acid