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Issue 13, 2018
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A reversible and highly selective two-photon fluorescent “on–off–on” probe for biological Cu2+ detection

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Abstract

A two-photon active probe for physiological copper (Cu2+) detection is expected to play an important role in monitoring biological metabolism. Herein, a novel Schiff base derivative (E)-2,2′-((4-((4-(diethylamino)-2-hydroxybenzylidene)amino)phenyl)azanediyl)bis(ethan-1-ol) (L) with remarkable two-photon activity was developed and synthetically investigated. L presents high selectivity and sensitivity for Cu2+ sensing in ethanol/HEPES buffer (v/v, 1 : 1), which is accompanied by the fluorescence switching “off” and subsequently “on” with the addition of EDTA. The mechanism for the detection of Cu2+ is further analyzed using 1H NMR titration, mass spectra and theoretical calculations. Furthermore, since the probe L possesses good photophysical properties, excellent biocompatibility and low cytotoxicity, it is successfully applied to track Cu2+ in the cellular endoplasmic reticulum by two-photon fluorescence imaging, showing its potential value for practical applications in biological systems.

Graphical abstract: A reversible and highly selective two-photon fluorescent “on–off–on” probe for biological Cu2+ detection

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Publication details

The article was received on 31 Jan 2018, accepted on 05 Mar 2018 and first published on 05 Mar 2018


Article type: Paper
DOI: 10.1039/C8OB00257F
Citation: Org. Biomol. Chem., 2018,16, 2264-2268
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    A reversible and highly selective two-photon fluorescent “on–off–on” probe for biological Cu2+ detection

    H. Wang, B. Fang, L. Zhou, D. Li, L. Kong, K. Uvdal and Z. Hu, Org. Biomol. Chem., 2018, 16, 2264
    DOI: 10.1039/C8OB00257F

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