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Bioorg Med Chem Lett. 2013 May 15;23(10):2916-9. doi: 10.1016/j.bmcl.2013.03.052. Epub 2013 Mar 25.

Rhodamine-based 'turn-on' fluorescent probe for Cu(II) and its fluorescence imaging in living cells.

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  • 1State Key Laboratory of Fine Chemicals, Dalian University of Technology, 2 Linggong Rd., Hi-tech Zone, Dalian 116024, People's Republic of China.


A novel rhodamine spirolactam derivative 3',6'-Bis(diethylamino)-2-(2-hydroxyethylamino) spiro[isoindoline-1,9'-xanthen]-3-one (RO1) was synthesized, and characterized by high-resolution mass spectrometry (HRMS), X-ray crystallography, Infrared spectroscopy (IR), and (1)H NMR and (13)C NMR spectroscopy. RO1 exhibited highly sensitive and exclusively selective fluorescence response toward Cu(2+) over other metal ions with a detection limit of 0.56ppb in mixed aqueous solution. The fluorescence was pH-independent in the wide range pH 3.1-11.6. The turn-on fluorescence enhancement of the probe is based on Cu(2+) induced ring-opening mechanism of the rhodamine spirolactam. Moreover, by means of fluorescence microscopy experiments, it was demonstrated that RO1 could monitor trace Cu(2+) changes by live cell imaging.

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