title: An excited state intramolecular proton transfer dye based fluorescence turn-on probe for fast detection of thiols and its applications in bioimaging.
abstract: In this study, a new fluorescent probe 2-(2'-hydroxy-5'-N-maleimide phenyl)-benzothiazole (probe 1), was designed and synthesized by linking the excited state intramolecular proton transfer (ESIPT) fluorophore to the maleimide group for selective detection of thiols in aqueous solution. The fluorescence of probe 1 is strongly quenched by maleimide group through the photo-induced electron transfer (PET) mechanism, but after reaction with thiol, the fluorescence of ESIPT fluorophore is restored, affording a large Stokes shifts. Upon addition of cysteine (Cys), probe 1 exhibited a fast response time (complete within 30s) and a high signal-to-noise ratio (up to 23-fold). It showed a high selectivity and excellent sensitivity to thiols over other relevant biological species, with a detection limit of 3.78×10-8M (S/N=3). Moreover, the probe was successfully applied to the imaging of thiols in living cells.
authors.affiliation: Department of Chemistry, Taiyuan Normal University, Jinzhong 030619, China. Electronic address: yunzhao@tynu.edu.cn.
authors.forename: Yun
authors.initials: Y
authors.lastname: Zhao
authors.affiliation: School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China.
authors.forename: Yuanyuan
authors.initials: Y
authors.lastname: Xue
authors.affiliation: Department of Chemistry, Taiyuan Normal University, Jinzhong 030619, China.
authors.forename: Haoyang
authors.initials: H
authors.lastname: Li
authors.affiliation: Department of Chemistry, Taiyuan Normal University, Jinzhong 030619, China.
authors.forename: Ruitao
authors.initials: R
authors.lastname: Zhu
authors.affiliation: Department of Chemistry, Taiyuan Normal University, Jinzhong 030619, China.
authors.forename: Yuehong
authors.initials: Y
authors.lastname: Ren
authors.affiliation: Department of Chemistry, Taiyuan Normal University, Jinzhong 030619, China.
authors.forename: Qinghua
authors.initials: Q
authors.lastname: Shi
authors.affiliation: Department of Chemistry, Taiyuan Normal University, Jinzhong 030619, China.
authors.forename: Song
authors.initials: S
authors.lastname: Wang
authors.affiliation: School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China. Electronic address: guow@sxu.edu.cn.
authors.forename: Wei
authors.initials: W
authors.lastname: Guo
mesh_terms: D002470:Cell Survival; D003545:Cysteine / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D006863:Hydrogen-Ion Concentration; D021621:Imaging, Three-Dimensional; D011522:Protons; D013050:Spectrometry, Fluorescence; D013438:Sulfhydryl Compounds / Q000032:analysis*; D013997:Time Factors
chemical_list: D005456:Fluorescent Dyes; D011522:Protons; D013438:Sulfhydryl Compounds; D003545:Cysteine
keywords: Cell imaging; ESIPT; Fluorescent probe; PET; Thiols