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

[Display omitted] 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...

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Published inChinese chemical letters Vol. 30; no. 12; pp. 2169 - 2172
Main Authors Shao, Zhuzhou, Zhang, Chun, Zhu, Xiaohua, Wang, Yajun, Xu, Wenyuan, Chen, Yu, Wang, Xiaoming, Zhu, Hailiang, Liang, Yong
Format Journal Article
LanguageEnglish
Published Elsevier B.V 01.12.2019
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China%State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210023, China
Subjects
1,8-Naphthalimide
Bioorthogonal cycloaddition
Photophysical property
Sydnone
Turn-on fluorescence
Sydnone
Turn-on fluorescence
1,8-Naphthalimide
Photophysical property
Bioorthogonal cycloaddition
1
8-Naphthalimide
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Summary:[Display omitted] 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.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2019.06.023