A novel cyanobiphenyl benzothiazole-based fluorescent probe for detection of biothiols with a large Stokes shift and its application in cell imaging. Issue 5 (2nd February 2017)

• Record Type: Journal Article
• Authors: Chen, Song; Li, Hongmei; Hou, Peng
• Is Part Of: Tetrahedron. Volume 73:Issue 5(2017)
• Page Start: 589
• Page End: 593
• Publication Date: 2017-02-02
• Subjects: ESIPT -- Fluorescent probe -- Cell imaging -- Thiols -- PET; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.12.049
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: An ESIPT-based fluorescent probe (Probe1 ) with a large Stokes shift (202 nm) for the sensing of biothiols has been developed based on cyanobiphenyl benzothiazole derivative exhibiting larger Stokes shift than 2-(benzothiazol-2-yl)phenol. This probe with 2, 4-dinitrobenzenesulfonate (DNBS) as a highly thiol-selective group was constructed based on the combination of excited state intramolecular proton transfer (ESIPT) and photoinduced electron transfer (PET) mechanisms. Upon the treatment with biothiols, this probe produced a remarkable fluorescence enhancement at 482 nm. The detect limits for Cys, GSH and Hcy was calculated to be as low as 2.0 × 10 −8 M, 1.7 × 10 −7 M and 1.2 × 10 −7 M, respectively (based on S/N = 3). Importantly, application of this probe was successfully demonstrated by imaging thiols in living NCI-H226 cells. Graphical abstract: An ESIPT-based fluorescent probe with a large Stokes shift (202 nm) for the sensing of biothiols has been developed based on cyanobiphenyl benzothiazole derivative exhibiting larger Stokes shift than 2-(benzothiazol-2-yl)phenol.