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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
Bioorganic & Medicinal Chemistry ( IF 3.5 ) Pub Date : 2018-02-17 , DOI: 10.1016/j.bmc.2018.02.030
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.



中文翻译:

基于罗丹明B和2,5-吡咯烷二酮部分的新型“关闭”化学传感器的合成和评估,用于选择性区分活细胞中的谷胱甘肽及其生物成像

基于罗丹明B染料和2,5-吡咯烷二酮部分,合成并表征了一种新的“开启”荧光探针RDMBM。通过紫外可见光谱和荧光光谱技术评估了其对各种氨基酸的感应行为。观察到的光谱变化表明RDMBM在MeOH / H 2 O(1:2,v / v,pH 7.40,Tris-HCl缓冲液,1 mM)溶液中显示出对GSH的高选择性和敏感性,并且经历了1:1的共价结合与GSH。更重要的是,若丹明B衍生物的螺环结构中氮原子的氢化和开环与不同基团的诱导作用紧密相关。此外,荧光成像应用表明RDMBM 可以成功用于人类乳腺癌细胞MCF-7中GSH的检测。

更新日期:2018-02-17
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