Jiangsu Key Laboratory for Pharmacology and Safety Evaluation of Chinese Materia Medica, Department of Pharmacy, Nanjing University of Chinese Medicine, 138 Xianlin Rd., 210023, PR China.
School of Environmental and Biological Engineering, Nanjing University of Science and Technology, 200 Xiaolinwei, Nanjing 210094, PR China; School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, PR China.
Bioorg Med Chem. 2018 May 1;26(8):1823-1831. doi: 10.1016/j.bmc.2018.02.030. Epub 2018 Feb 17.
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/HO (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.
一种新的“开启”型荧光探针 RDMBM，基于罗丹明 B 染料和 2,5-吡咯烷二酮部分合成并进行了表征。通过紫外可见和荧光光谱技术评估了其对各种氨基酸的传感行为。观察到的光谱变化表明，RDMBM 在 MeOH/HO（1:2，v/v，pH 7.40，Tris-HCl 缓冲液，1 mM）溶液中对 GSH 表现出高选择性和灵敏度，并且它与 GSH 发生 1:1 的共价结合。更重要的是，螺环结构中氮原子的加氢和开环与不同基团的诱导效应紧密结合。此外，荧光成像应用表明，RDMBM 可成功用于检测人乳腺癌细胞 MCF-7 中的 GSH。
