A highly sensitive and reductant-resistant fluorescent chemodosimeter for the rapid detection of nitroxyl

• Published in: Sensors and actuators. B, Chemical Vol. 220; pp. 727 - 733
• Main Authors: Liu, Caiyun, Cao, Zimin, Wang, Zihao, Jia, Pan, Liu, Jin, Wang, Zuokai, Han, Bingjun, Huang, Xin, Li, Xin, Zhu, Baocun, Zhang, Xiaoling
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01-12-2015
• Subjects: 2-(2′-Hydroxyphenyl)benzothiazole; 2-(Diphenylphosphino)benzoate; Actuators; Bioimaging; Biomedical materials; Cells (biology); Fluorescence; Fluorescent chemodosimeter; Hydrogen sulfide; In vivo testing; In vivo tests; Nitroxyl; 2-(2′-Hydroxyphenyl)benzothiazole; Bioimaging; Nitroxyl; Fluorescent chemodosimeter; 2-(Diphenylphosphino)benzoate
• ISSN: 0925-4005; 1873-3077
• DOI: 10.1016/j.snb.2015.06.013

A highly sensitive and reductant-resistant fluorescent chemodosimeter was designed and synthesized to rapidly detect HNO in aqueous solution and living cells.
•A novel fluorescent probe HNO-HBT was designed and synthesized to detect HNO.•The high selectivity is ascribed to the use of 2-(diphenylphosphino)benzoate group.•The addition of HNO leads to the 40-fold fluorescence enhancement.•HNO-HBT shows high sensitivity (LOD 50nM) and rapid response (within 5min) to HNO.•HNO-HBT can monitor the changes of intracellular HNO level in living cells.
Nitroxyl (HNO) has attracted increasing attention for its ability to enhance myocardial contractility and vasorelaxation in heart failure. However, studies of the detailed functions and mechanisms of HNO in vivo are hampered by a lack of reliable detection methods. Herein, we report a novel 2-(diphenylphosphino)benzoate-caged 2-(2′-hydroxyphenyl)benzothiazole fluorescent chemodosimter (HNO-HBT) for the sensitive and rapid detection of HNO in living cells. HNO-HBT exhibits high HNO-selectivity even in the presence of high concentration of biological reductants including glutathione (GSH), hydrogen sulfide (H2S) and ascorbate (AA), which is ascribed to the adoption of the 2-(diphenylphosphino)benzoate recognition moiety. In addition, the results showed that HNO-HBT could quantitatively detect HNO in the range of 0–40μM with the detection limit of 50nM. Importantly, HNO-HBT was successfully applied to the fluorescence imaging of HNO levels in living cells, and it is expected to be a useful chemical tool for investigating the detailed functions and mechanisms of HNO in living systems.