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Issue 23, 2019
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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

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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.

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

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Publication details

The article was received on 10 Sep 2019, accepted on 01 Oct 2019 and first published on 03 Oct 2019


Article type: Paper
DOI: 10.1039/C9AN01778J
Analyst, 2019,144, 6922-6927

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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

    W. Chen, M. Yang, N. Luo, F. Wang, R. Yu and J. Jiang, Analyst, 2019, 144, 6922
    DOI: 10.1039/C9AN01778J

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