Citation: Jia Shaokang, Yang Shixi, Ji Huimin, Peng Shuang, Chen Kun, He Zhiyong, Zhou Xiang. Systematic investigation of bioorthogonal cellular DNA metabolic labeling in a photo-controlled manner[J]. Chinese Chemical Letters, ;2020, 31(5): 1104-1108. doi: 10.1016/j.cclet.2019.10.021 shu

Systematic investigation of bioorthogonal cellular DNA metabolic labeling in a photo-controlled manner

College of Chemistry and Molecular Sciences, Key Laboratory of Biomedical Polymers of Ministry of Education, Wuhan University, Wuhan 430072, China

hezy@whu.edu.cn

xzhou@whu.edu.cn

Received Date: 19 September 2019
Revised Date: 17 October 2019
Accepted Date: 18 October 2019
Available Online: 24 October 2019

Figures(5)

Bioorthogonal cleavage and ligation reactions together form one more integrated system about the repertoire of bioorthogonal chemistry, capacitating an array of thrilling new biological applications. The bond-cleavage type and position of biomolecular remain a great challenge, which determines the metabolic pathway of the targets in living systems. Herein we designed two linkages of methylene and carbonyl group attached the N-3 position of the 5-ethynyl-2'-deoxyuridine (EdU) base or the oxygen atom at deoxyribose 3' position to a photocaging group, which would be cleaved by irradiation with 365 nm ultraviolet light. EdU derivatives linked by methylene at the N-3 position had better photodecage efficiency and stability in the absence of light. This paper provides a strategy for studying the nucleoside metabolic pathways in cells, which can easily and conveniently evaluate the effect of the position and type of the linkages. The developed strategy affords a reference for controlling spatial and temporal metabolism of small-molecule drugs, allowing direct manipulation of intact cells under physiological conditions.
- DNA metabolic labeling,
- Bioorthogonal chemistry,
- Photocage group,
- Modified nucleoside,
- Cell imaging
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