A Facile, Versatile, and Highly Efficient Strategy for Peroxynitrite Bioimaging Enabled by Formamide Deformylation.

Authors:
Xilei Xie
Xilei Xie
Institute of Materia Medica
China
Guangzhao Liu
Guangzhao Liu
Nantong University
Yong Li
Yong Li
Huaihe Hospital of Henan University
Kaifeng | China
Yawen Liu
Yawen Liu
Karolinska Institutet
Sweden
Xu Wang
Xu Wang
Affiliated People's Hospital of Jiangsu University
China
Bo Tang
Bo Tang
Shandong Normal University

Anal Chem 2019 May 29;91(10):6872-6879. Epub 2019 Apr 29.

College of Chemistry, Chemical Engineering and Materials Science, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong , Shandong Normal University , Jinan 250014 , People's Republic of China.

Peroxynitrite (ONOO) is attracting increasing attention due to its involvement in multiple facets of pathophysiological processes. However, ONOO bioimaging is still challenging due to (1) the lack of highly specific reaction triggers, (2) the tedious and low-yielding synthesis of current sophisticated probes, and (3) the lack of availability of a versatile chemical strategy. To address these challenges, on the basis of amine formylation/deformylation chemistry, we have developed a novel strategy for ONOO bioimaging. As proof of principle, we designed, synthesized, and evaluated four novel fluorescent probes equipped with the formamide functionality. Although they feature distinctly different fluorophore classes, all probes can be synthesized in one step in high yields and exhibit particularly specific, highly sensitive, and rapid responses to ONOO. The bioimaging capability is well demonstrated by successfully visualizing ONOO fluctuation in live cells and major organs of mice suffering from paraquat poisoning. The proposed strategy has proved to be a facile, versatile, and highly efficient methodology for ONOO visualization, which will greatly facilitate ONOO biochemistry and pathophysiology.

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Source
http://dx.doi.org/10.1021/acs.analchem.9b01175DOI Listing
May 2019
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