Citation: Shao Zhuzhou, Zhang Chun, Zhu Xiaohua, Wang Yajun, Xu Wenyuan, Chen Yu, Wang Xiaoming, Zhu Hailiang, Liang Yong. Design of a 1, 8-naphthalimide-based OFF-ON type bioorthogonal reagent for fluorescent imaging in live cells[J]. Chinese Chemical Letters, ;2019, 30(12): 2169-2172. doi: 10.1016/j.cclet.2019.06.023 shu

Design of a 1, 8-naphthalimide-based OFF-ON type bioorthogonal reagent for fluorescent imaging in live cells

Shao Zhuzhou ^a,1 ,
Zhang Chun ^a,1 ,
Zhu Xiaohua ^b,1 ,
Wang Yajun ^a,1 ,
Xu Wenyuan ^a ,
Chen Yu ^a ,
Wang Xiaoming ^b ,
Zhu Hailiang ^b,*, ,
Liang Yong ^a,*,

a.
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China
b.
State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210023, China

zhuhl@nju.edu.cn

yongliang@nju.edu.cn

Received Date: 16 April 2019
Revised Date: 11 June 2019
Accepted Date: 13 June 2019
Available Online: 14 December 2019

Figures(4)

A novel 1, 8-naphthalimide-based OFF-ON type fluorogenic sydnone (Naph-Syd) is designed as bioorthogonal probe for imaging. Sydnone moiety efficiently quenches the native fluorescence of 1, 8-naphthalimide, which can be restored with the enhancement of about 300-fold, after reacting with strained cyclooctynes to form pyrazole products (Naph-Pyr). The second-order rate constant of this bioorthogonal cycloaddition can be up to 2.5 L mol^-1 s^-1, which benefits imaging of biomolecules at low concentrations in cellular environment.
- Bioorthogonal cycloaddition,
- 1, 8-Naphthalimide,
- Photophysical property,
- Sydnone,
- Turn-on fluorescence
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