title: A mitochondria-targeted turn-on fluorescent probe for the detection of glutathione in living cells.
abstract: A novel turn-on red fluorescent BODIPY-based probe (Probe 1) for the detection of glutathione was developed. Such a probe carries a para-dinitrophenoxy benzyl pyridinium moiety at the meso position of a BODIPY dye as self-immolative linker. Probe 1 responds selectively to glutathione with the detection limit of 109nM over other amino acids, common metal ions, reactive oxygen species, reactive nitrogen species, and reactive sulfur species. A novel electrostatic interaction to modulate the SNAr attack of glutathione was believed to play significant role for the observed selective response to glutathione. The cleavage of dinitrophenyl ether by glutathione leads to the production of para-hydroxybenzyl moiety which is able to self-immolate through an intramolecular 1,4-elimination reaction to release the fluorescent BODIPY dye. The low toxic probe has been successfully used to detect mitochondrial glutathione in living cells.
authors.affiliation: School of Pharmacy, Fudan University, Shanghai 201203, PR China.
authors.forename: Jian
authors.initials: J
authors.lastname: Zhang
authors.affiliation: School of Pharmacy, Fudan University, Shanghai 201203, PR China.
authors.forename: Xiaolong
authors.initials: X
authors.lastname: Bao
authors.affiliation: School of Pharmacy, Fudan University, Shanghai 201203, PR China.
authors.forename: Junliang
authors.initials: J
authors.lastname: Zhou
authors.affiliation: Key Laboratory for Special Functional Materials of the Ministry of Education, Henan University, Kaifeng 475004, PR China.
authors.forename: Fangfang
authors.initials: F
authors.lastname: Peng
authors.affiliation: School of Pharmacy, Fudan University, Shanghai 201203, PR China.
authors.forename: Hang
authors.initials: H
authors.lastname: Ren
authors.affiliation: School of Pharmacy, Fudan University, Shanghai 201203, PR China.
authors.forename: Xiaochun
authors.initials: X
authors.lastname: Dong
authors.affiliation: School of Pharmacy, Fudan University, Shanghai 201203, PR China; Key Laboratory for Special Functional Materials of the Ministry of Education, Henan University, Kaifeng 475004, PR China. Electronic address: zhaoweili@fudan.edu.cn.
authors.forename: Weili
authors.initials: W
authors.lastname: Zhao
mesh_terms: D001593:Benzyl Compounds / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D005978:Glutathione / Q000032:analysis*; D006367:HeLa Cells; D006801:Humans; D057230:Limit of Detection; D018613:Microscopy, Confocal; D008928:Mitochondria / Q000737:chemistry* / Q000648:ultrastructure; D008958:Models, Molecular; D061848:Optical Imaging / Q000379:methods*; D011726:Pyridinium Compounds / Q000737:chemistry*; D013050:Spectrometry, Fluorescence / Q000379:methods; D055672:Static Electricity
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001593:Benzyl Compounds; D001896:Boron Compounds; D005456:Fluorescent Dyes; D011726:Pyridinium Compounds; D005978:Glutathione
keywords: BODIPY; Fluorescence imaging; Fluorescent probe; Glutathione; Mitochondria-targeted