3411-95-8Relevant articles and documents
Developing a novel ratiometric fluorescent probe based on ESIPT for the detection of pH changes in living cells
Song, Wenhui,Dong, Baoli,Lu, Yaru,Lin, Weiying
, p. 1696 - 1701 (2019)
As an important parameter of intracellular metabolism, pH plays important roles in maintaining normal physiological processes. The abnormal pH could cause disorder of cell function which may cause neurological diseases. Herein, we present two novel ratiometric fluorescent probes to detect pH changes. The probes employed 2-(2′-hydroxyphenyl)benzothiazole as fluorescent platform, and displayed desirable fluorescence response to pH on the basis of excited state intramolecular proton transfer (ESIPT) process. The probe BtyC-1 showed green fluorescence at 546 nm under acidic conditions, while it displayed strong blue fluorescence at 473 nm and weak green fluorescence at 546 nm under alkaline conditions. Biological experiments demonstrated that the probe BtyC-1 could be successfully applied for the ratiometric imaging of cellular pH and the NH4Cl-induced pH changes in living cells.
An ESIPT-based highly selective and sensitive probe for the detection of hydrogen sulfide
Xu, Pengfei,Liu, Meihui,Gao, Tang,Zhang, Hailiang,Li, Ziwei,Huang, Xinyi,Zeng, Wenbin
, p. 4007 - 4010 (2015)
Abstract A new excited state intramolecular proton transfer dye with red keto emission (620 nm) and remarkably large Stokes shift (240 nm) was discovered. Based on its unique red emission and large Stokes shift, it was developed to a novel fluorescent probe which can highly selectively and sensitively detect hydrogen sulfide.
Observation of the generation of peroxynitrite in mouse liver after acetaminophen overdose with a boronate-based ratiometric fluorescence probe
Ma, Ying,Tian, Haigang,Jin, Zhengyu,Li, Xiaoyong,Li, Yiping
, p. 6510 - 6514 (2019)
A ratiometric fluorescent probe, BTPB, for the selective monitoring of hepatic peroxynitrite (ONOO-) in situ after acetaminophen (APAP) overdose has been developed. Our study provided direct evidence for supporting the generation of ONOO- in APAP-induced liver injury. This new probe will be a useful tool for studying the roles of ONOO-in vivo.
Benzothiazoline based chemodosimeters for fluorogenic detection of hypochlorous acid
Wu, Zhisheng,Wu, Xuanjun,Li, Zhu,Yang, Yuhui,Han, Jiahuai,Han, Shoufa
, p. 4354 - 4357 (2013)
Two nonfluorescent and colorless chemodosimeters featuring benzothiazoline moiety were developed for chromo-fluorogenic detection of HOCl.
A water-soluble esipt fluorescent probe with high quantum yield and red emission for ratiometric detection of inorganic and organic palladium
Gao, Tang,Xu, Pengfei,Liu, Meihui,Bi, Anyao,Zeng, Wenbin,Hu, Pengzhi,Ye, Bin,Wang, Wei
, p. 1142 - 1145 (2015)
A novel fluorescent probe with a high quantum yield (0.41), large Stokes shifts (255 nm), and red emission (635 nm) was designed to detect all typical oxidation states of palladium species (0, +2, +4) by palladium-mediated terminal propargyl ethers cleavage reaction in water solution without any organic media. The probe showed a high selectivity and excellent sensitivity for palladium species, with a detection as low as 57 nM (6.2 μgL-1).
Synthesis, Characterization, Properties and DFT Calculations of 2-(Benzo[b]thiophen-2-yl)pyridine-based Iridium(III) Complexes with Different Ancillary Ligands
Li, Gao-Nan,Zeng, Yong-Pi,Li, Kai-Xiu,Chen, Hao-Hua,Xie, Hui,Zhang, Fu-Lin,Chen, Guang-Ying,Niu, Zhi-Gang
, p. 323 - 331 (2016)
A series of new cyclometalated btp-based iridium(III) complexes with three different ancillary ligands, Ir(btp)2(bozp) (3a), Ir(btp)2(btzp) (3b) and Ir(btp)2(izp) (3c) (btp = 2-(benzo[b]thiophen-2-yl)pyridine, bozp =2-(benzo[d]oxazol-2-yl)phenol, btzp =2-(benzo[d]thiazol-2-yl)phenol, izp = 2-(2 H-indazol-2-yl)phenol), have been synthesized and fully characterized. The crystal structure of 3b has been determined by single crystal X-ray diffraction analysis. A comparative study has been carried out for complexes 3a - 3c by UV-vis absorption spectroscopy, photoluminescence spectroscopy, cyclic voltammetry and DFT calculations. This observation illustrates that the substitution of N or S in ancillary ligand can lead to a marked bathochromic shift of absorption and emission wavelengths. The spectroscopic characterisation of these complexes has been complemented by DFT and TD-DFT calculations, supporting the assignment of 3MLCT/3LC to the lowest energy excited state.
Fluorometric determination of Au3+ via hydrolysis of thiocarbonate with bromide as a masking agent
Park, So Young,Choi, Myung Gil,Lim, Dae Sung,Chang, Suk-Kyu
, p. 14 - 19 (2019)
Gold ions are very important in chemistry and materials science owing to their various uses in chemical reactions as well as industrial and biological applications. In this study, we developed a novel reaction-based probe (GP), which is a thiocarbonate derivative of the 2-(2-hydroxyphenyl)benzothiazole dye, for the selective and sensitive determination of Au3+. The probe GP showed turn-on fluorescence signaling behavior toward Au3+ ions triggered by the metal-induced hydrolysis of the thiocarbonate group. Interference from other thiophilic ions, Ag+ and Hg2+, was effectively eliminated by using bromide ions as a masking agent. Prominent off–on type fluorescent sensing of Au3+ over other coexisting metal ions was possible with a detection limit of 4.8 × 10?8 M (9.5 ppb). Fluorescence sensing of Au3+ by GP was fast and applicable over a wide pH range between 4.0 and 10.5. Application of the probe to the analysis of Au3+ in synthetic wastewater was conducted using an easily accessible smartphone.
A reversible, benzothiazole-based “Turn-on” fluorescence sensor for selective detection of Zn2+ ions in vitro
Musib, Dulal,Raza, Md Kausar,Devi, Salam Sujata,Roy, Mithun
, (2020)
Abstract: Temperature-driven, highly sensitive and selective “TURN-ON” fluorometric detection of Zn2+ by benzothiazole-based probes (L1 and L2) was reported in physiological pH in the present work. Iron(II) acted as the reversible switch or trigger for the reversible detection of Zn2+ ions by the probes resulting in “TURN-OFF” fluorescence at room temperature. However, selective detection of Zn2+ in the presence of Fe2+ was irreversible at 0–5 °C. Such temperature dependence on reversible fluorometric detection of Zn2+ in the presence of Fe2+ was explained from the thermodynamic perspective as well as DFT calculations in which the absolute enthalpy (H) and Gibbs free energy (G) of the resultant complexes and the fluorophores (L1 and L2) at different temperatures were determined. Enhanced fluorescence of the Zn2+ bound probes was due to the inhibition of excited-state intramolecular proton transfer (ESIPT). Effect of solvents, pH, and temperature on the fluorometric detection of Zn2+ was also probed in the present work. The results were translated into the visual detection of Zn2+ on paper-based fluorescence probe and later we demonstrated the sensing of mobile Zn2+ ions by the probes in living HeLa cells as the proof of concept of our present investigations. Graphic Abstract: A benzothiazole-based, “TURN-ON” fluorescent sensor was developed for selective and reversible detection of Zn2+in vitro, in which Fe2+ acted as the reversible switch. [Figure not available: see fulltext.].
A "turn-On" fluorescent probe for sensitive and selective detection of fluoride ions based on aggregation-induced emission
Du, Man,Huo, Baolong,Li, Mengwen,Shen, Ao,Bai, Xue,Lai, Yaru,Liu, Jiemin,Yang, Yunxu
, p. 32497 - 32505 (2018)
Based on the fluorophore of 2-(2′-hydroxyphenyl)benzothiazole (HBT) with aggregation-induced emission (AIE) properties, a highly selective and sensitive fluorescent probe PBT towards F- was investigated. "Turn-On" fluorescence type signaling was realized by employing fluoride-selective cleavage of the latent thiophosphinated probe in mixed aqueous media. The probe is designed in such a way that the excited state intramolecular proton transfer (ESIPT) of the HBT moiety becomes blocked. The chemodosimetric approach of F- to the probe results in the recovery of the ESIPT by removal of a free AIE-active HBT moiety through a subsequent hydrolysis process. The F- detection limit of the probe was 3.8 nM in the dynamic range of 0.5 μM to 10 μM. In addition, the proposed probe has been used to detect F- in water samples and toothpaste samples with satisfying results.
A Turn on ESIPT Probe for Rapid and Ratiometric Fluorogenic Detection of Hg2+ and its Application in Live-Cell Imaging
Zhang, Di,Liu, Jihong,Yin, Haiyan,Wang, Hongqi,Li, Shufang,Wang, Min,Li, Man,Zhou, Ling,Zhang, Junfeng
, p. 1367 - 1372 (2016)
A probe based on 2-(2′-hydroxyphenyl) benzothiazole (HBT) and thiophosphate has been synthesized and used for the ratiometric detection of Hg2+. The probe was designed in such a way that the excited state intramolecular proton transfer (ESIPT) of the HBT moiety get blocked. The probe exhibited a strong fluorescence enhancement upon addition of Hg2+ while showing almost no response to other cations in CH3CN/HEPES buffer solution. The probe exhibited fast selectivity towards Hg2+ and could be completed in 1?min. Fluorescence imaging experiments of Hg2+ in living TE-1 cells demonstrated its value of practical applications in biological systems.
