Design of a 1,8-naphthalimide-based OFF-ON type bioorthogonal reagent for fluorescent imaging in live cells |
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| Authors: | Zhuzhou Shao Chun Zhang Xiaohua Zhu Yajun Wang Wenyuan Xu Yu Chen Xiaoming Wang Hailiang Zhu Yong Liang |
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| Institution: | 1. State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China;2. State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210023, China |
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| Abstract: | 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. |
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| Keywords: | Corresponding authors Bioorthogonal cycloaddition 1 8-Naphthalimide Photophysical property Sydnone Turn-on fluorescence |
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