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1.
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
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.
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
4.
A Ratiometric Fluorescent Probe Based on a Through‐Bond Energy Transfer (TBET) System for Imaging HOCl in Living Cells
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Dr. Yan‐Ru Zhang Dr. Ning Meng Prof. Dr. Jun‐Ying Miao Prof. Dr. Bao‐Xiang Zhao 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(52):19058-19063
A simple ratiometric probe (Naph‐Rh) has been designed and synthesized based on a through‐bond energy transfer (TBET) system for sensing HOCl. In this probe, rhodamine thiohydrazide and naphthalene formyl were connected by simple synthesis methods to construct a structure of monothio‐bishydrazide. Free probe Naph‐Rh showed only the emission of naphthalene. When probe Naph‐Rh reacted with HOCl, monothio‐bishydrazide could be converted into 1,2,4‐oxadiazole, which not only ensured that the donor and the acceptor were connected with electronically conjugated bonds, but also resulted in the spiro‐ring opening and the emission of rhodamine. Therefore, a typical TBET process took place. The probe possessed high‐energy transfer efficiency and large pseudo‐Stokes shifts. As the first TBET probe for HOCl, Naph‐Rh showed excellent selectivity and sensitivity toward HOCl over other reactive oxygen species (ROS)/reactive nitrogen species (RNS), and could respond fast to a low concentration of HOCl in the real sample. In addition, the probe was suitable for imaging HOCl in living cells due to its real‐time response, excellent resolution, and reduced cytotoxicity. 相似文献
5.
A rhodamine 6G hydrazide fluorescent chemosensor was prepared for the rapid HOCl detection in aqueous media. The system makes good use of the irreversible HOCl-mediated selective oxidation reaction to generate fluorescent response proportional to the amount of HOCl in neutral buffer. This probe exhibits great photostability, high sensitivity, and good selectivity for HOCl over other reactive species and most of the common metal ions. Furthermore, the probe is cell membrane permeable, and its applicability has been successfully demonstrated for fluorescence imaging of both exogenous and endogenous HOCl within living cells. Cytotoxicity assays prove that this probe is almost nontoxic to the cultured cell lines under the experimental conditions. 相似文献
6.
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
7.
Influence of Donor on the Sensing Performance of a Series of Through‐Bond Energy Transfer‐Based Two‐photon Fluorescent Cu2+ Probes
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Optical properties of a series of molecular two‐photon fluorescent Cu2+ probes containing the same acceptor (rhodamine group) are analyzed using time‐dependent density functional theory in combination with analytical response theory. Special emphasis is placed on evolution of the probes' optical properties in the presence of Cu2+. In this study, the compound with naphthalene as the donor is shown to be excellent ratiometric fluorescent chemosensor, whereas the compound with quinoline derivative as the donor shows off/on‐typed colorimetric fluorescent response. For the compound with naphthalimide derivative as the donor, changing the connection between the donor and acceptor can efficiently prevent the fluorescent quenching of the probe both in the absence and presence of Cu2+. The donor moiety and the connection between donor and acceptor are thus found to play dominant roles on sensing performance of these probes. Moreover, distributions of molecular orbitals involved in the excitation and emission of the probes are analyzed to explore responsive mechanism of the probes. The through‐bond energy transfer process is theoretically demonstrated. Our results are used to elucidate the available experimental measurements. This work is helpful to understand the relationships of structure with optical properties for the studied probes. 相似文献
8.
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
9.
《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
10.
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
11.
Chun-Yan Li Chun-Xiang Zou Yong-Fei Li Xue-Fei Kong Yu Zhou Yin-Shuang Wu Wei-Guo Zhu 《Analytica chimica acta》2013
A rhodamine spirolactam derivative (1) was developed as a colormetric and fluorescent chemosensor for adenosine-5′-triphosphate (ATP) via hydrogen bonds interaction. As far as we know, this is the first case to explore ATP-induced ring-opening of spirolactam in rhodamine derivatives. It exhibited a highly sensitive “turn-on” fluorescent response toward ATP with a 47-fold fluorescence intensity enhancement under 20 equiv. of ATP added. The chemosensor can be applied to the quantification of ATP with a linear range covering from 1.0 × 10−7 to 2.0 × 10−4 M and a detection limit of 2.5 × 10−8 M. The experiment results show that the response behavior of 1 toward ATP is pH independent in medium condition (pH 6.0–8.0). Most importantly, the novel chemosensor has well solved the problem of serious interferences from other nucleoside polyphosphates such as ADP and AMP generally met by previously reported typical fluorescent chemosensors for ATP. Moreover, the response of the chemosensor toward ATP is fast (response time less than 3 min). In addition, the chemosensor can be used for the fluorescence assay for protein kinase activity with satisfactory results. The chemosensor for ATP based on hydrogen bonds interaction provided a novel strategy for the design of colormetric and ratiometric fluorescent probes for other target anions with high sensitivity and selectivity. 相似文献
12.
13.
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
14.
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
15.
Julia Modrzejewska Marcin Szala Aleksandra Grzelakowska Magorzata Zakos-Szyda Jacek Zielonka Radosaw Podsiady 《Molecules (Basel, Switzerland)》2021,26(19)
Derivatives of coumarin, containing oxidant-sensitive boronate group, were recently developed for fluorescent detection of inflammatory oxidants. Here, we report the synthesis and the characterization of 3-(2-benzothiazolyl)-7-coumarin boronic acid pinacol ester (BC-BE) as a fluorescent probe for the detection of peroxynitrite (ONOO–), with high stability and a fast response time. The BC-BE probe hydrolyzes in phosphate buffer to 3-(2-benzothiazolyl)-7-coumarin boronic acid (BC-BA) which is stable in the solution even after a prolonged incubation time (24 h). BC-BA is slowly oxidized by H2O2 to form the phenolic product, 3-benzothiazol-2-yl-7-hydroxy-chromen-2-one (BC-OH). On the other hand, the BC-BA probe reacts rapidly with ONOO−. The ability of the BC-BA probe to detect ONOO– was measured using both authentic ONOO– and the system co-generating steady-state fluxes of O2•– and •NO. BC-BA is oxidized by ONOO– to BC-OH. However, in this reaction 3-benzothiazol-2-yl-chromen-2-one (BC-H) is formed in the minor pathway, as a peroxynitrite-specific product. BC-OH is also formed in the reaction of BC-BA with HOCl, and subsequent reaction of BC-OH with HOCl leads to the formation of a chlorinated phenolic product, which could be used as a specific product for HOCl. We conclude that BC-BA shows potential as an improved fluorescent probe for the detection of peroxynitrite and hypochlorite in biological settings. Complementation of the fluorescence measurements by HPLC-based identification of oxidant-specific products will help to identify the oxidants detected. 相似文献
16.
Super‐quenched Molecular Probe Based on Aggregation‐Induced Emission and Photoinduced Electron Transfer Mechanisms for Formaldehyde Detection in Human Serum
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Haitao Yang Fujia Wang Jilin Zheng Hao Lin Prof. Dr. Bin Liu Prof. Dr. Yi‐Da Tang Prof. Dr. Chong‐Jing Zhang 《化学:亚洲杂志》2018,13(11):1432-1437
Energy transfer between fluorescent dyes and quenchers is widely used in the design of light‐up probes. Although dual quenchers are more effective in offering lower background signals and higher turn‐on ratios than one quencher, such probes are less explored in practice as they require both quenchers to be within the proximity of the fluorescent core. In this contribution, we utilized intramolecular motion and photoinduced electron transfer (PET) as quenching mechanisms to build super‐quenched light‐up probes based on fluorogens with aggregation‐induced emission. The optimized light‐up probe possesses negligible background and is able to detect not only free formaldehyde (FA) but also polymeric FA, with an unprecedented turn‐on ratio of >4900. We envision that this novel dual quenching strategy will help to develop various light‐up probes for analyte sensing. 相似文献
17.
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
18.
Eiji Nakata Khongorzul Gerelbaatar Futa Komatsubara Takashi Morii 《Molecules (Basel, Switzerland)》2022,27(21)
Fluorescence imaging is a powerful technique for continuous observation of dynamic intracellular processes of living cells. Fluorescent probes bearing a fluorescence switching property associated with a specific recognition or reaction of target biomolecule, that is, stimuli-responsibility, are important for fluorescence imaging. Thus, fluorescent probes continue to be developed to support approaches with different design strategies. When compared with simple intensity-changing fluorescent probes, ratiometric fluorescent probes typically offer the advantage of less sensitivity to errors associated with probe concentration, photobleaching, and environmental effects. For intracellular usage, ratiometric fluorescent probes based on small molecules must be loaded into the cells. Thus, probes having intrinsic fluorescence may obscure a change in intracellular signal if the background fluorescence of the remaining extracellular probes is high. To overcome such disadvantages, it is necessary to minimize the extracellular background fluorescence of fluorescent probes. Here, the design strategy of the latent ratiometric fluorescent probe for wash-free ratiometric imaging using a xanthene dye seminapthorhodafluor (SNARF) as the scaffold of fluorophore is discussed. 相似文献
19.
20.
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