A fluorescent probe emitting in near-infrared region for sensitive and selective detection of biothiols in both solution and living cells. Issue 52 (30th December 2015)

• Record Type: Journal Article
• Authors: Chen, Wenqiang; Luo, Hongchen; Liu, Xingjiang; Qi, Fengpei; Yang, Dalei; Song, Xiangzhi
• Is Part Of: Tetrahedron letters. Volume 56:Issue 52(2015)
• Page Start: 7176
• Page End: 7179
• Publication Date: 2015-12-30
• Subjects: Biothiols -- Fluorescent probe -- Near-infrared -- Tetrahydroquinoxaline -- Cell imaging; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.11.040
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: A fluorescent probe with an emission in near-infrared region was developed for sensitive and selective detection of biothiols. Moreover, this probe was successfully applied to visualize biothiols in living cells. Abstract: A fluorescent probe, 1, 4-diethyl-7-(3-pyridin-2-yl-acroyloyl)-1, 2, 3, 4-tetrahydro-5-oxa-1, 4-diazaanthracen-6-one (probe1 ), with an emission in near-infrared region was developed for sensitive and selective detection of biothiols. Probe1 is essentially non-fluorescent due to the strong intramolecular charge transfer (ICT) from the electron-donating tetrahydroquinoxaline moiety to the electron-withdrawing pyridine group. Upon the treatment with biothiols, the conjugation system was broken via Michael addition reaction between biothiols and α, β-unsaturated ketone, which inhibited the ICT process and resulted in a remarkable fluorescence enhancement with an emission maximum at 660 nm. Moreover, probe1 was successfully applied to image intracellular thiols in living cells.