A novel AIEE and EISPT fluorescent probe for selective detection of cysteine. Issue 33 (16th August 2017)

• Record Type: Journal Article
• Authors: Zhou, Xiaohong; Guo, Dong; Jiang, Yuren; Gong, Da-min; Zhao, Xiong-jie; Zhou, Li-yun
• Is Part Of: Tetrahedron letters. Volume 58:Issue 33(2017)
• Page Start: 3214
• Page End: 3218
• Publication Date: 2017-08-16
• Subjects: Aggregation-induced emission enhancement -- Excited state intramolecular proton transfer -- Cysteine -- Bioimaging; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.06.084
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A novel fluorescent probe based on ESIPT and AIEE was used to detect Cys. The probe showed a high selectivity for Cys over GSH, Hcy and other amino acid. The detection limit for Cys was 0.05 µM with a linear range of 0–90 µM. The probe has been successfully applied for bioimaging in living cells. Abstract: We designed and synthesized a simple and readily available fluorescent probe3 for cysteine (Cys) based on naphthalene derivative. The probe is composed of a new class of aggregation-induced emission enhancement (AIEE) active dye2 based on excited-state intramolecular proton transfer (ESIPT) and an acrylate group as the Cys recognition unit as well as the ESIPT blocking agent, which can be cut off by Cys from the probe in aqueous solution with mild conditions. The probe had great sensitivity and selectivity for the detection of Cys over homocysteine (Hcy) and glutathione (GSH) with a detection limit of 0.05 µM. In addition, we have successfully applied the probe for bioimaging studies of Cys in living cells, indicating that the probe holds great potential for biological applications.