Synthesis and evaluation of a novel ‘off-on’ chemical sensor based on rhodamine B and the 2,5-pyrrolidinedione moiety for selective discrimination of glutathione and its bioimaging in living cells

Publication date: Available online 17 February 2018
Source:Bioorganic & Medicinal Chemistry
Author(s): Zhenzhen Xue, Lu Xiao, Hailang Chen, Tong Zhou, Yangyan Qian, Jinshuai Suo, Qinhan Hua, Baojing Zhou, Renlong Ye, Xiaofeng Bao, Jing Zhu
A new "turn-on" fluorescent probe, RDMBM, based on the rhodamine B dye and the 2, 5-pyrrolidinedione moiety was synthesized and characterized. Its sensing behavior toward various amino acids was evaluated via UV–vis and fluorescence spectroscopic techniques. The observed spectral changes showed that RDMBM displays high selectivity and sensitivity toward GSH in MeOH/H2O (1:2, v/v, pH 7.40, Tris-HCl buffer, 1 mM) solution and that it undergoes 1:1 covalent binding with GSH. More importantly, the hydrogenation and ring-opening of the nitrogen atom in the spirane structure of rhodamine B derivatives were tightly bound to the induction effects of different groups. Furthermore, fluorescence imaging applications demonstrated that RDMBM can be successfully used for the detection of GSH in human breast cancer cells MCF-7.

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