A selective fluorescence probe for H2S from biothiols with a significant regioselective turn-on response and its application for H2S detection in living cells and in living Caenorhabditis elegans

• Published in: Sensors and actuators. B, Chemical Chemical, 2018-12, Vol.276, p.456-465
• Main Authors: Yang, Bing, Su, Mi-Mi, Xue, Yun-Sheng, He, Zhen-Xiang, Xu, Chen, Zhu, Hai-Liang
• Format: Article
• Language: English
• Subjects: Curcumin; Fluorescence probe; H2S; Imaging; Regioselective
• ISSN: 0925-4005; 1873-3077
• DOI: 10.1016/j.snb.2018.08.138

[Display omitted] •CP-1 is a new probe for H2S with a significant regioselective turn-on response.•CP-1 features superb selectivity to H2S, and has over 10000-fold selectivity for H2S from biothiols such as GSH.•The actual minimal detectable concentration of CP-1 to H2S is low to 50 nM.•CP-1 could provide a set of sectionalized linear standard curves from 0 to 275 μM.•CP-1 has been successfully applied for imaging exogenous and endogenous H2S in living cells and Caenorhabditis elegans. A selective probe with a significant regioselective turn-on response, CP-1, has been developed for detection of H2S from biothiols. CP-1 features superb selectivity to H2S, a wide pH range and low cytotoxicity. CP-1 has over 10000-fold selectivity for H2S from biothiols such as GSH. With the actual detected concentration low to 50 nM, CP-1 could provide a set of sectionalized linear standard curves to cover a 0 to 275 μM detecting range accurately. NMR and HRMS spectra confirmed that the detection process was a regioselective reaction. Furthermore, mono-protected compound FL-1 has been synthesized and tested for Na2S and biothiols. All test results demonstrate that the detection can only occur in one side of CP-1. With high sensitivity and selectivity, CP-1 could be further used in rat urine samples system. Moreover, CP-1 has been applied in the imaging of exogenous and endogenous H2S in living cells and in living Caenorhabditis elegans.