共查询到20条相似文献,搜索用时 31 毫秒
1.
Shan Wang Beitong Zhu Bingya Wang Xinhua Cao Lei Zhu Ji-Ting Hou Lintao Zeng 《中国化学快报》2021,32(5):1795-1798
The reactive oxygen species (ROS) are tightly associated with endoplasmic reticulum (ER) stress. Thus, the deep and visual insight of aberrant ROS fluctuations in the ER can help us better investigate the ER stress-associated pathology. In this work, a fluorescent probe ERC for HOCl detection in the ER based on phenothiazine-derived coumarin platform was developed. In the presence of HOCl, ERC exhibited an emission change from 609 nm to 503 nm within seconds. It also showed high sensitivity (0.44 μmol/L) and superb photostability. Significantly, ERC displayed low cytotoxicity, good cell membrane permeability, and appreciable ER-targetability. Ultimately, the probe was successfully utilized to image exogenous and endogenous HOCl in living cells and reveal the HOCl burst in cisplatin-treated cancer cells. 相似文献
2.
Lin Yuan Prof. Weiying Lin Yinan Xie Bin Chen Jizeng Song 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(9):2700-2706
Hypochlorous acid (HOCl), a reactive oxygen species (ROS), plays a significant biological role in living systems. However, abnormal levels of HOCl are implicated in many inflammation‐associated diseases. Therefore, the detection of HOCl is of great importance. In this work, we describe the HOCl‐promoted cyclization of rhodamine‐thiosemicarbazides to rhodamine‐oxadiazoles, which is then exploited as a novel design strategy for the development of a new fluorescence turn‐on HOCl probe 2 . On the basis of the fluorescence resonance energy transfer (FRET) signaling mechanism, 2 was further converted into 1 a and 1 b , which represent the first paradigm of FRET‐based ratiometric fluorescent HOCl probes. The outstanding features of 1 a and 1 b include well‐resolved emission peaks, high sensitivity, high selectivity, good functionality at physiological pH, rapid response, low cytotoxicity, and good cell‐membrane permeability. Furthermore, these excellent attributes enable us to demonstrate, for the first time, the ratiometric imaging of endogenously produced HOCl in living cells by using these novel ratiometric probes. We expect that 1 a and 1 b will be useful molecular tools for studies of HOCl biology. In addition, the HOCl‐promoted cyclization reaction of rhodamine‐thiosemicarbazides to rhodamine‐oxadiazoles should be widely applicable for the development of different types of fluorescent HOCl probes. 相似文献
3.
A BODIPY-based ratiometric fluorescent probe for HOCl has been designed based on the transduction of thioether to sulfoxide function. This probe features a marked absorption and emission blue-shift upon the HOCl-promoted rapid transduction, enabling the highly selective and ratiometric detection. In addition, the probe works excellently within a wide pH range of 4–10, addressing the existing pH dependency issue. Living cells studies demonstrate that the probe is cell membrane permeable and can be employed successfully to image endogenous HOCl generation in macrophage cells. 相似文献
4.
A boron dipyrromethene (BODIPY)-based fluorometric probe, HCS, has been successfully developed for the highly sensitive and selective detection of hypochlorous acid (HOCl). The probe is based on the specific HOCl-promoted oxidation of methyl phenyl sulfide. The reaction is accompanied by a 160-fold increase in the fluorescent quantum yield (from 0.003 to 0.480). The fluorescent turn-on mechanism is accomplished by suppression of photoinduced electron transfer (PET) from the methyl phenyl sulfide group to BODIPY. The fluorescence intensity of the reaction between HOCl and HCS shows a good linearity in the HOCl concentration range 1–10 μM. The detection limit is 23.7 nM (S/N = 3). In addition, confocal fluorescence microscopy imaging using RAW264.7 macrophages demonstrates that the HCS probe could be an efficient fluorescent detector for HOCl in living cells. 相似文献
5.
Yahui Chena Tingwen Wei Zhijie Zhang Wei Zhang Jing Lv Tiantian Chen Bo Chi Fang Wang Xiaoqiang Chen 《中国化学快报》2017,28(10):1957-1960
A new fl uorescent probe 1 was designed for mitochondrial localization and ratiometric detection of hypochlorite in living cells. It is noteworthy that a high Pearson’s co-localization coeffi cient (Rr) we have obtained was calculated to be 0.97. 相似文献
6.
Yuan L Lin W Xie Y Chen B Song J 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(9):2700-2706
Hypochlorous acid (HOCl), a reactive oxygen species (ROS), plays a significant biological role in living systems. However, abnormal levels of HOCl are implicated in many inflammation-associated diseases. Therefore, the detection of HOCl is of great importance. In this work, we describe the HOCl-promoted cyclization of rhodamine-thiosemicarbazides to rhodamine-oxadiazoles, which is then exploited as a novel design strategy for the development of a new fluorescence turn-on HOCl probe 2. On the basis of the fluorescence resonance energy transfer (FRET) signaling mechanism, 2 was further converted into 1a and 1b, which represent the first paradigm of FRET-based ratiometric fluorescent HOCl probes. The outstanding features of 1a and 1b include well-resolved emission peaks, high sensitivity, high selectivity, good functionality at physiological pH, rapid response, low cytotoxicity, and good cell-membrane permeability. Furthermore, these excellent attributes enable us to demonstrate, for the first time, the ratiometric imaging of endogenously produced HOCl in living cells by using these novel ratiometric probes. We expect that 1a and 1b will be useful molecular tools for studies of HOCl biology. In addition, the HOCl-promoted cyclization reaction of rhodamine-thiosemicarbazides to rhodamine-oxadiazoles should be widely applicable for the development of different types of fluorescent HOCl probes. 相似文献
7.
8.
A BODIPY-based fluorescent probe, HBP, was developed for the detection of hypochlorous acid based on the specific hypochlorous acid-promoted oxidative intramolecular cyclization of heterocyclic hydrazone in response to the amount of HOCl. The reaction is accompanied by a 41-fold increase in the fluorescent quantum yield (from 0.004 to 0.164). The fluorescence intensity of the reaction between HOCl and HBP is linear in the HOCl concentration range of 1–8 μM with a detection limit of 2.4 nM (S/N = 3). Confocal fluorescence microscopy imaging using RAW264.7 cells showed that the new probe HBP could be used as an effective fluorescent probe for detecting HOCl in living cells. 相似文献
9.
Hongjuan Tong Yajun Zhang Shengnan Ma Minghao Zhang Na Wang Rui Wang Kaiyan Lou Wei Wang 《中国化学快报》2018,29(1):139-142
A pinacol boronate caged NIAD-4 derivative was demonstrated to be a near-infrared fluorescent probe for fast and selective detection of hypochlorite over other ROS species. 相似文献
10.
Levels of reactive oxygen species(ROS) in cancer cells or in the tumor microenvironment differ noticeably from those in normal cells and cellular microenvironments because ROS play important roles in all aspects of tumor physiology. However, due to the lack of adequate tools, it is difficult to study the relationship between ROS, especially certain types of ROS(e.g., HOCl), and cancer. We report herein an HOCl-specific fluorescent probe, FDOCl-20, containing a thiocarbamide group as a receptor, for the visualization of HOCl in solid tumors in vivo. This probe displays high selectivity and sensitivity to HOCl, and is appropriate for use in acidic conditions, including the tumor microenvironment. Using FDOCl-20 as a tool, we can visualize HOCl in solid tumors in vivo. Importantly, the fluorescent intensity of FDOCl-20 is proportional to tumor volume. Thus, FDOCl-20 is a useful tool to investigate the relationship between HOCl and the physiological processes of tumors. 相似文献
11.
We have developed a ratiometric fluorescent probe BRT based on boron dipyrromethene (BODIPY) and rhodamine-thiohydrazide Förster resonance energy transfer (FRET) platform for sensing hypochlorous acid (HOCl) with high selectivity and sensitivity. The probe can detect HOCl in 15 s with the detection limit of 38 nM. Upon mixing with HOCl the fluorescence colour of probe BRT changed from green to orange. Moreover, probe BRT was applied to successfully monitor HOCl in living RAW 264.7 cells. 相似文献
12.
Xianhui Wang Yuanfang Tao Jian Zhang Miao Chen Nannan Wang Xin Ji Weili Zhao 《化学:亚洲杂志》2020,15(6):770-774
Herein, a red‐emitting fluorescent probe DM‐BDP‐OCl containing a para‐DMTC benzyl pyridinium moiety at the meso position of BODIPY as self‐immolative portion for the detection of HOCl was designed and synthesized. DM‐BDP‐OCl exhibited excellent specificity and a fast response for HOCl beyond other ROS/RNS. It was used for the accurately measurable detection of HOCl with a linear range from 0 μM to 50 μM, and the detection limit for HOCl reached 60 nM. Moreover, the probe could directly monitor fluctuations of exogenous and endogenous HOCl in living HeLa and RAW 264.7 cells. This work provided a powerful and convenient imaging tool for probing pathological and physiological actions of HOCl. 相似文献
13.
Fluorescent probes have been widely employed in biological imaging and sensing. However, it is always a challenge to design probes with high sensitivity. In this work, based on rhodamine skeleton, we developed a general strategy to construct sensitivity-enhanced fluorescent probe with the help of theoretical calculation for the first time. As a proof of concept, we synthesized a series of HOCl probes. Experiment results showed that with the C-9 of pyronin moiety of rhodamine stabilized by an electron donor group, probe DQF-S exhibited an importantly enhanced sensitivity (LOD: 0.2 nmol/L) towards HOCl together with fast response time (<10 s). Moreover, due to the breaking symmetrical electron distribution by another electron donor group, the novel rhodamine probe DQF-S displayed a far red to near-infrared emission (>650 nm) and large Stokes shift. Bioimaging studies indicated that DQF-S can not only effectively detect basal HOCl in various types of cells, but also be successfully applied to image tumor tissue in vivo. These results demonstrate the potential of our design as a useful strategy to develop excellent fluorescent probes for bioimaging. 相似文献
14.
Yanhui Zhang Hao Teng Ying Gao Muhammad Wasim Afzal Jingye Tian Xi Chen Haoyang Tang Tony D. James Yuan Guo 《中国化学快报》2021,31(11):2917-2920
Triazolopyridines are an important kind of fused-ring compounds. A HOCl-promoted triazolopyridine formation strategy is reported here for the first time in which hypochlorous acid (HOCl) mildly and efficiently promotes the formation of 1,2,4-triazolo[4,3-a]pyridines NT1-NT6 from various 2-pyridylhydrazones N1-N6. N6, a rhodol-pyridylhydrazone hybrid, was developed into a fluorescent probe for the selective detection of HOCl, and successfully applied to probe endogenous HOCl in living cells and zebrafish in situ and in real time. The present intramolecular cyclization reaction is selective and atom-economical, thereby not only providing an important approach for the convenient synthesis of triazolopyridines, but also offering a general strategy for sensitive, selective and biocompatible detection of endogenous HOCl in complex biosystems. 相似文献
15.
Macrophages, important cells of the innate immune system, can produce abundant HOCl in the cytoplasm to fight against bacteria. Recent studies suggest that mitochondria in macrophages play a role in antibacterial responses. During bacterial infection, however, it is uncertain whether HOCl is present in the mitochondria, mainly because of the lack of a suitable research method. Herein, by developing a new mitochondrial-targeting fluorescent HOCl probe, combined with confocal fluorescence imaging, we show for the first time that HOCl can appear in the mitochondria of macrophages (Raw264.7 cells) during bacterial infection, as confirmed with non-phagocytic cells and inhibitors as control experiments. Moreover, the developed probe exhibits an accurate mitochondrial-targeting ability, a fast response, and high selectivity and sensitivity (detection limit 9 nM), and is thus expected to be employed for further revealing the biological function of subcellular mitochondria. 相似文献
16.
《中国化学快报》2020,31(11):2980-2984
Fluorescent probes have been widely employed in biological imaging and sensing. However, it is always a challenge to design probes with high sensitivity. In this work, based on rhodamine skeleton, we developed a general strategy to construct sensitivity-enhanced fluorescent probe with the help of theoretical calculation for the first time. As a proof of concept, we synthesized a series of HOCl probes. Experiment results showed that with the C-9 of pyronin moiety of rhodamine stabilized by an electron donor group, probe DQF-S exhibited an importantly enhanced sensitivity (LOD: 0.2 nmol/L) towards HOCl together with fast response time (<10 s). Moreover, due to the breaking symmetrical electron distribution by another electron donor group, the novel rhodamine probe DQF-S displayed a far red to near-infrared emission (>650 nm) and large Stokes shift. Bioimaging studies indicated that DQF-S can not only effectively detect basal HOCl in various types of cells, but also be successfully applied to image tumor tissue in vivo. These results demonstrate the potential of our design as a useful strategy to develop excellent fluorescent probes for bioimaging. 相似文献
17.
Hypochlorous acid (HOCl), one of the reactive oxygen species (ROS), is a key microbicidal agent which is used for natural defense. However, it is also linked to varieties of human diseases owing to the overproduction of HOCl. Much effort has been made to exploit selective fluorescent sensors for the detection of HOCl, but most of them have some disadvantages such as short excitation wavelength, low selectivity, and slow response and so on. These restrict the biological application of the probes. In this work, BR-O was designed and synthesized on the base of phenoxazine for the detection of HOCl. BR-O exhibited a violent fluorescence enhancement in the presence of HOCl, showing excellent selectivity and high sensitivity. More importantly, the probe BR-O was capable of detecting exogenous and endogenous HOCl in living cells. 相似文献
18.
The endogenous hypochlorous acid(HOCl) has been evidenced in a variety of cellular courses. However, the role of HOCl in most pathophysiological processes still keeps unclear because of the limited detecting tools. In this work, we presented the pre- paration of a phenothiazine-derived fluorescent probe ClO-1 for HOCl detection with a cyanopyridinium moiety to improve its water solubility and lengthen its emission wavelength. The HOCl-promoted oxidation of sulfur atom in the probe resulted in a 460-fold emission intensity enhancement at 635 nm with high selectivity and sensitivity(detection limit: 1.12 nmol/L). The rapid response(5 s) also endowed the probe with real-time detection ability. Successfully, ClO-1 was devoted to the bioimaging of endogenous HOCl in inflamed RAW 264.7 cells and 5-fluorouracil-treated MCF-7 cells. 相似文献
19.
A fluorescent probe, HKOCl-1, has been successfully developed for the detection of hypochlorous acid on the basis of a specific reaction with p-methoxyphenol. The formation of HOCl has been successfully detected not only in an abiotic system but also in an enzymatic system (myeloperoxidase/H2O2/Cl(-) system) and in living macrophage cells upon stimulation. This new probe might be used as an efficient tool for probing the roles HOCl plays in biological systems. 相似文献
20.
《中国化学快报》2020,31(11):2917-2920
Triazolopyridines are an important kind of fused-ring compounds. A HOCl-promoted triazolopyridine formation strategy is reported here for the first time in which hypochlorous acid (HOCl) mildly and efficiently promotes the formation of 1,2,4-triazolo[4,3-a]pyridines NT1-NT6 from various 2-pyridylhydrazones N1-N6. N6, a rhodol-pyridylhydrazone hybrid, was developed into a fluorescent probe for the selective detection of HOCl, and successfully applied to probe endogenous HOCl in living cells and zebrafish in situ and in real time. The present intramolecular cyclization reaction is selective and atom-economical, thereby not only providing an important approach for the convenient synthesis of triazolopyridines, but also offering a general strategy for sensitive, selective and biocompatible detection of endogenous HOCl in complex biosystems. 相似文献