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Selective Visualization of Live-Cell Mitochondrial Thiophenols and Their Induced Oxidative Stress Process by a Rationally Designed Rhodol-Based Fluorescent Probe
摘要： Mitochondria as cellular powerhouses are the preferential targets affected by thiophenols, an important class of highly toxic environmental pollutants, and are linked to the production of pathogenic reactive oxygen species (ROS) induced by trace thiophenol residues. For real-time and accurate sensing, it is critically important to develop highly sensitive fluorescent probes for the specific detection of mitochondrial thiophenols. Herein, we report the first mitochondria-targeted fluorescent probe (ROAL) to image thiophenols in living cells. The development of ROAL was based on a novel red-emitting rhodol derivative (ROAP). ROAL proved to be highly selective to thiophenols among various analytes including aliphatic thiols, and renders an ultrasensitive off-on fluorescence response to thiophenols with a remarkable detection limit (8.1 nM). The probe efficiently stains mitochondria with a high Pearson’s co-localization coefficient (0.95) using Mito Tracker Green FM as reference, thereby ensuring the specific detection of mitochondrial thiophenols in living HepG2 and HeLa cells. In particular, using this probe we for the first time proved that endogenous reactive oxygen species have the capacity to eliminate thiophenols in living cells, suggesting that thiophenols might induce cellular oxidative stress.
关键词： oxidative stress damage,fluorescent probe,live-cell imaging,thiophenol,mitochondria-targeted
更新于2025-09-23 15:19:57
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Synthesis, characterization, thermal and luminescent properties of thiophenol-functionalized platinum(II) bis(acetylide) complexes
摘要： Two thiophenol-functionalized trans-platinum(II) bis(acetylide) complexes, having one thiophenol moiety in each alkenyl backbone with general formula trans-[(PPh3)2Pt{C≡C–Ar–CH=CH(SC6H5)}2], (2a–2b), (Ar = phenylene or 2,5-dimethylphenylene), were synthesized in good yields and good regioselectivities. Compared to the absorption bands of the trans-platinum(II) bis(acetylide) complexes 1, the positions of the lowest energy absorption bands were redshifted by 17–18 nm, after functionalization with thiophenol. For both of the platinum(II) complexes 2, the lowest energy absorption bands in chloroform solution at room temperature were observed in the range 376–379 nm, and under excitation at the absorption maximum both complexes showed emission maxima in the range of 408–419 nm. All the new Pt complexes have been characterized by physico-chemical and spectroscopic methods.
关键词： thermal properties,thiophenol-functionalized,characterization,synthesis,platinum(II) bis(acetylide) complexes,luminescent properties
更新于2025-09-10 09:29:36
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A highly sensitive and selective “off-on” porphyrin-based fluorescent sensor for detection of thiophenol
摘要： Thiophenol and its derivatives easily cause damage to aquatic bioorganisms, animals and even human being, therefore, fluorescent probes for detecting thiophenol with sensitive and selective characters are highly popular. In this study, a highly sensitive and selective porphyrin-based fluorescent sensor (M1) was reported for detection of thiophenol based on the steric hindrance effect, where the recognition unit, 7-nitrobenzo[c][1,2,5]oxadiazolyl group is linked to aromatic ortho-position in the porphyrin, and correspondingly the fluorescence of fluorescein is efficiently quenched. Its time of fluorescence response for thiophenol was only 60s, and its fluorescence responses for the other anions/molecules were all far lower than the relative fluorescence ratio values for thiophenol, which means that the porphyrin-based fluorescent sensor is rapid, sensitive and selective to detection of thiophenol. This approach offers some useful insights for designing sensitive and selective fluorescent turn-on sensors in the detection assays for other analytes.
关键词： thiophenol,7-nitrobenzo[c][1,2,5]oxadiazolyl group,steric hindrance effect,the porphyrin-based fluorescent sensor
更新于2025-09-09 09:28:46
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Iridium(III) complex-based fluorescent probe for detection of thiophenols and its application in water samples
摘要： In consideration of the nucleophilic capacity of thiophenols, which could cleave sulfonamide under neutral conditions, a cyclometalated iridium(III) complex (probe 1) comprised 2,4-dinitrobenzenesulfonamide (DNBS) as the recognition unit was designed and synthesized to high selectivity and sensitivity detect thiophenols successfully based on internal charge transfer (ICT) mechanism. Upon addition with thiophenols to 20% DMSO/PBS solution of nearly non-fluorescent probe 1 (10 μM, pH = 7.4), fluorescent product (complex 2) was formed after cleavage of DNBS group and a significant emission enhancement at 470 nm was observed. In addition, it could be successfully applied to detect thiophenol in water samples with a high recovery, confirming its practical value in environment science.
关键词： Iridium(III) complex,2,4-dinitrobenzenesulfonamide,Thiophenol,Fluorescent probe
更新于2025-09-09 09:28:46
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Highly sensitive fluorescent probe based on a novel phenothiazine dye for detection of thiophenols in real water samples and living cells
摘要： Based on an excited-state intramolecular proton transfer (ESIPT) fluorophore, a novel fluorescent off-on probe for detection of thiophenols was designed and synthesized. This probe (λex = 401 nm, λem = 527 nm) displayed high specificity for sensing thiophenols over other biologically related species. Besides, this probe possessed capabilities of monitoring thiophenols with rapid response rate (3 min), a large Stokes shift (126 nm), and high sensitivity (2.7 nM). The sensing mechanism was considered to be that thiophenols triggered thiolysis of the probe and the ESIPT fluorophore was released, as confirmed by means of HPLC and HRMS. Most notably, this probe was successfully applied to monitor levels of thiophenols in realistic samples and MDA-MB-231 cells.
关键词： Thiophenol,Large stokes shift,Probe,MDA-MB-231 cells
更新于2025-09-04 15:30:14
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Electrogenerated Chemiluminescent Chemodosimeter Based on a Cyclometalated Iridium(III) Complex for Rapid and Sensitive Detection of Thiophenol
摘要： Thiophenol is the simplest aromatic thiol that is utilized for various applications in industry and agriculture. However, it should be used with care because thiophenol is readily absorbed into the human body by inhalation and ingestion, which leads to serious internal injuries. Thus, there is an urgent need for real-time and accurate monitoring of thiophenol. Despite remarkable advantages of electrogenerated chemiluminescence (ECL) analysis, ECL thiophenol probes have never been reported. Herein, a new strategy for the rapid detection of thiophenol using an ECL turn-on chemodosimeter based on a cyclometalated Ir(III) complex is described. This analytical system showed superior sensitivity (limit of detection (LOD) value, 3.8 nM) in comparison to the conventional fluorescence method. In addition, our system exhibited remarkable selectivity and reaction rate towards thiophenol over other analytes. Moreover, it was successfully applied to quantify thiophenol in real water samples, providing a new proof-of-concept for field-monitoring based on ECL.
关键词： Cyclometalated Ir(III) complex,Electrogenerated chemiluminescence,Chemodosimeter,Sensitive detection,Thiophenol
更新于2025-09-04 15:30:14