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. Issue 8 (1st May 2018)

• Record Type: Journal Article
• Authors: Xue, Zhenzhen; Xiao, Lu; Chen, Hailang; Zhou, Tong; Qian, Yangyan; Suo, Jinshuai; Hua, Qinhan; Zhou, Baojing; Ye, Renlong; Bao, Xiaofeng; Zhu, Jing
• Is Part Of: Bioorganic & medicinal chemistry. Volume 26:Issue 8(2018)
• Page Start: 1823
• Page End: 1831
• Publication Date: 2018-05-01
• Subjects: Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2018.02.030
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Highlights: A new fluorescent probe based on the rhodamine B 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. It displays high selectivity and sensitivity toward GSH in MeOH/H2 O (1:2, v/v, pH 7.40, Tris-HCl buffer, 1 mM) solution. It undergoes 1:1 covalent binding with GSH. Fluorescence imaging applications demonstrated that it can be used for the detection of GSH in human breast cancer cells MCF-7. Abstract: 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/H2 O (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.