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An intramolecular charge transfer and excited state intramolecular proton transfer based fluorescent probe for highly selective detection and imaging of formaldehyde in living cells.

Authors
  • Chen, Wen1
  • Yang, Mei
  • Luo, Na
  • Wang, Fenglin
  • Yu, Ru-Qin
  • Jiang, Jian-Hui
  • 1 State Key Laboratory of Chemo/Bio-Sensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China. [email protected] [email protected] , (China)
Type
Published Article
Journal
The Analyst
Publisher
The Royal Society of Chemistry
Publication Date
Nov 18, 2019
Volume
144
Issue
23
Pages
6922–6927
Identifiers
DOI: 10.1039/c9an01778j
PMID: 31660553
Source
Medline
Language
English
License
Unknown

Abstract

Formaldehyde (FA), as a reactive carbonyl species, is endogenously generated in various biological processes. Abnormal levels of FA could lead to various cellular dysfunction and pathological conditions. Here, we develop a new activatable fluorescent probe for highly selective visualization of FA in living cells. Our probe (Naph-1) is designed using a naphthalene derivative as the fluorophore and hydrazone as a recognition site for FA. Naph-1 is essentially nonemissive. After reacting with FA, the amine moiety is converted into a Schiff base with electron-withdrawing ability and the fluorescence is simultaneously turned on due to synergetic intramolecular charge transfer and favoured excited state intramolecular proton transfer effects. Naph-1 exhibits a large Stokes shift upon reaction with FA. Furthermore, it possesses high selectivity and superior sensitivity toward FA with an estimated limit of detection of 0.35 μM. Moreover, Naph-1 is also successfully applied to image both endogenous and exogenous formaldehyde in living cells. These features demonstrate that Naph-1 holds great potential in the detection and imaging of formaldehyde in biological systems.

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