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

Mao-Zhong Tian, Ming-Ming Hu, Jiang-Li Fan, Xiao-Jun Peng, Jing-Yun Wang, Shi-Guo Sun, Rong Zhang
Bioorganic & Medicinal Chemistry Letters 2013 May 15, 23 (10): 2916-9
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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