title: Target-triggered NIR emission with a large stokes shift for the detection and imaging of cysteine in living cells.
abstract: Background autofluorescence from biological systems generally reduces the sensitivity of a fluorescent probe for imaging biological targets. Addressing this challenge requires the development of fluorescent probes that produce emission in the near-infrared region. Herein, we report the design and synthesis of a fluorescent probe that generates an NIR emission with a large Stokes shift upon the selective response to Cys over Hcy and GSH. The probe is designed to consist of two Cys-sensing sites, an acrylate ester and an aldehyde installed ortho to each other. The reaction of the probe with Cys triggers an excited state intramolecular proton transfer process upon photo-excitation, thereby producing an NIR emission with a large Stokes shift. Accordingly, this probe hold great promise for the selective detection of Cys in biological systems. We further demonstrate the capacity of this probe for Cys imaging in living cells.
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science&Technology, Shanghai 200237 (P. R. China). zhaocchang@ecust.edu.cn.
authors.forename: Chunchang
authors.initials: C
authors.lastname: Zhao
authors.forename: Xiuai
authors.initials: X
authors.lastname: Li
authors.forename: Feiyi
authors.initials: F
authors.lastname: Wang
mesh_terms: D000179:Acrylates / Q000138:chemical synthesis* / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003545:Cysteine / Q000032:analysis*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D057054:Molecular Imaging / Q000379:methods*; D012680:Sensitivity and Specificity; D019265:Spectroscopy, Near-Infrared / Q000379:methods
chemical_list: D000179:Acrylates; D001896:Boron Compounds; D005456:Fluorescent Dyes; C000598972:PCys-B compound; D003545:Cysteine
keywords: NIR emission; biosensors; biothiols; excited state intramolecular proton transfer; fluorescent probes; imaging agents