Citation: Song Lun, Sun Xu-Dong, Ge Yu, Yao Yu-Hua, Shen Jie, Zhang Wei-Bing, Qian Jun-Hong. Anaphthalimide-based fluorescent probe for mercaptocontaining compounds[J]. Chinese Chemical Letters, ;2016, 27(12): 1776-1780. doi: 10.1016/j.cclet.2016.05.007 shu

Anaphthalimide-based fluorescent probe for mercaptocontaining compounds

Song Lun ^a ,
Sun Xu-Dong ^a ,
Ge Yu ^b ,
Yao Yu-Hua ^a ,
Shen Jie ^a ,
Zhang Wei-Bing ^a,, ,
Qian Jun-Hong ^a,,

a.
Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China
b.
Shanghai Institute of Quality Inspection and Technical, Shanghai 200233, China

Corresponding author: Zhang Wei-Bing, weibingzhang@ecust.edu.cn Qian Jun-Hong, junhongqian@ecust.edu.cn
Received Date: 26 February 2016
Revised Date: 28 April 2016
Accepted Date: 6 May 2016
Available Online: 18 December 2016

Figures(7)

A polarity-sensitive fluorescent probe MNP was rationally designed and synthesized with naphthalimide as the fluorophore and maleimide as the receptor for thiols. MNP is weakly fluorescent due to the photoinduced electron-transfer (PET) from the fluorophore to the receptor, and it displays evidently solvatochromic UV-vis and fluorescence spectra:the emission shifted from 495 nm in n-hexane to 545 nm in phosphate buffer solution. Michael addition reaction between thiols and the maleimide in MNP inhibited the PET process, which led to about eight-fold fluorescence enhancement. In addition, MNP showed highly sensitivity to mercapto-containing proteins and it could detect as low as 20.4 mg/mL of BSA in PBS. MNP has potential in fluorescent imaging of thiols in living cells.
- Polarity,
- Sulfur-containing proteins,
- Thiol,
- Fluorescent probe,
- Naphthalimide
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