RESUMO
Hypochlorous acid (HClO) as a kind of reactive oxygen species (ROS) plays a vital role in many biological processes. Organic fluorescence probes have attracted great interests for the detection of HClO, due to their relatively high selectivity and sensitivity, satisfactory spatiotemporal resolution and good biocompatibility. Constructing fluorescence probes to detect HClO with advantages of large Stokes shift, wide emission gap, near infrared emission and good water solubility is still challenging. In this work, a new ratiometric fluorescence probe (named HCY) for HClO was developed. FRET-based HCY was constructed by bonding a coumarin and a flavone fluorophore. In absence of HClO, HCY exists FRET process, however, FRET is inhibited in the presence of HClO because the conjugated double bond broke. Due to the good match of the emission spectrum of the donor and the absorption spectrum of the acceptor, the FRET system appears favorable energy transfer efficiency. HCY showed high sensitivity and rapid response time. The linearity between the ratios of fluorescence intensity and concentration of HClO was established with a low limit of detection. What's more, HCY was also applied for fluorescence images of HClO in RAW264.7 cells.
Assuntos
Transferência Ressonante de Energia de Fluorescência , Corantes Fluorescentes , Ácido Hipocloroso , Ácido Hipocloroso/análise , Transferência Ressonante de Energia de Fluorescência/métodos , Corantes Fluorescentes/química , Animais , Camundongos , Células RAW 264.7 , Cumarínicos/química , Limite de DetecçãoRESUMO
In this work, we developed a ratiometric fluorescent probe (NT) based on ICT framework in near-infrared (NIR) which could detect pH and viscosity simultaneously. Long emission wavelength in NIR could protect the probe from interference of background fluorescence and improve the accuracy of the test. Due to the presence of thiazole-salt, the probe possessed good water solubility and could respond immediately to pH in water system. The pH values measured by NT in the actual samples were not much different from that measured by the pH meter, therefore, NT could give excellent accuracy. NT realized the reversible detection of pH by protonation and deprotonation. NT was used successfully to detect the pH of actual water samples, human serum and meat, as well as the viscosity variation caused by thickeners. Additionally, NT could monitor the changes of pH and viscosity in living cells. Therefore, the novel probe exhibited potential application in the fields of the environment, human health and food safety evaluation.
Assuntos
Corantes Fluorescentes , Corantes Fluorescentes/química , Concentração de Íons de Hidrogênio , Viscosidade , Humanos , Espectrometria de Fluorescência , Espectroscopia de Luz Próxima ao Infravermelho/métodos , Animais , Carne/análise , Células HeLa , Água/químicaRESUMO
Hydrogen peroxide (H2O2) and viscosity play vital roles in the cellular environment as signaling molecule and microenvironment parameter, respectively, and are associated with many physiological and pathological processes in biological systems. We developed a near-infrared fluorescent probe, CQ, which performed colorimetric and ratiometric detection of H2O2 and viscosity based on the FRET mechanism, and was capable of monitoring changes in viscosity and H2O2 levels simultaneously through two different channels. Based on the specific reaction of H2O2 with borate ester, CQ exhibited a significant ratiometric response to H2O2 with a large Stokes shift of 221 nm, a detection limit of 0.87 µM, a near-infrared emission wavelength of 671 nm, a response time of 1 h, a wide detection ranges of 0.87-800 µM and a high energy transfer efficiency of 99.9 %. CQ could also recognize viscosity by the TICT mechanism, and efficiently detect viscosity changes caused by food thickeners. More importantly, CQ could successfully detect endogenous/exogenous H2O2 and viscosity in live HeLa cells, which was expected to be a practical tool for detecting H2O2 and viscosity in live cells.
Assuntos
Transferência Ressonante de Energia de Fluorescência , Corantes Fluorescentes , Peróxido de Hidrogênio , Peróxido de Hidrogênio/análise , Peróxido de Hidrogênio/química , Corantes Fluorescentes/química , Humanos , Células HeLa , Transferência Ressonante de Energia de Fluorescência/métodos , Viscosidade , Raios Infravermelhos , Limite de Detecção , Sobrevivência CelularRESUMO
BACKGROUND: Sulfur dioxide (SO2) is a significant gas signaling molecule in organisms, and viscosity is a crucial parameter of the cellular microenvironment. They are both involved in regulating many physiological processes in the human body. However, abnormalities in SO2 and viscosity levels are associated with various diseases, such as cardiovascular disease, lung cancer, respiratory diseases, neurological disorders, diabetes and Alzheimer's disease. Hence, it is essential to explore novel and efficient fluorescent probes for simultaneously monitoring SO2 and viscosity in organisms. RESULTS: We selected quinolinium salt with good stability, high fluorescence intensity, good solubility and low cytotoxicity as the fluorophore and developed a highly sensitive ratiometric probe QQD to identify SO2 and viscosity changes based on Förster resonance energy transfer/twisted intramolecular charge transfer (FRET/TICT) mechanism. Excitingly, compared with other probes for SO2 detection, QQD not only identified HSO3-/SO32- with a large Stokes shift (218 nm), low detection limit (1.87 µM), good selectivity, high energy transfer efficiency (92 %) and wide recognition range (1.87-200 µM), but also identified viscosity with a 26-fold fluorescence enhancement and good linearity. Crucially, QQD was applied to detect HSO3-/SO32- and viscosity in actual water and food samples. In addition, QQD had low toxicity and good photostability for imaging HSO3-/SO32- and viscosity in cells. These results confirmed the feasibility and reliability of QQD for HSO3-/SO32- and viscosity imaging and environmental detection. SIGNIFICANCE: We reported a unique ratiometric probe QQD for detecting HSO3-/SO32- and viscosity based on the quinolinium skeleton. In addition to detecting HSO3-/SO32- and viscosity change in actual water and food samples, QQD could also monitor the variations of HSO3-/SO32- and viscosity in cells, which provided an experimental basis for further exploration of the role of SO2 derivatives and viscosity in biological systems.
Assuntos
Transferência Ressonante de Energia de Fluorescência , Corantes Fluorescentes , Corantes Fluorescentes/química , Corantes Fluorescentes/síntese química , Viscosidade , Humanos , Dióxido de Enxofre/análise , Sulfitos/análise , Sulfitos/química , Limite de Detecção , Compostos de Quinolínio/químicaRESUMO
BACKGROUND: Sulfur dioxide (SO2) is a common gaseous pollutant that significantly threatens environmental pollution and human health. Meanwhile, viscosity is an essential parameter of the intracellular microenvironment, manipulating many physiological roles such as nutrient transport, metabolism, signaling regulation and apoptosis. Currently, most of the fluorescent probes used for detecting SO2 derivatives and viscosity are single-emission probes or probes based on the ICT mechanism, which suffer from short emission wavelengths, small Stokes shifts or susceptibility to environmental background. Therefore, the development of powerful high-performance probes for real-time monitoring of sulfur dioxide derivatives and viscosity is of great significance for human health. RESULTS: In this research, we designed the fluorescent probe QQC to detect SO2 derivatives and viscosity based on FRET platform with quinolinium salt as donor and quinolinium-carbazole as acceptor. QQC exhibited a ratiometric fluorescence response to SO2 with a low detection limit (0.09 µM), large Stokes shift (186 nm) and high energy transfer efficiency (95 %), indicating that probe QQC had good sensitivity and specificity. In addition, QQC was sensitive to viscosity, with an 9.10-folds enhancement of orange fluorescence and an excellent linear relationship (R2 = 0.98) between the logarithm of fluorescence intensity at 592 nm and viscosity. Importantly, QQC could not only recognize SO2 derivatives in real water samples and food, but also detect viscosity changes caused by food thickeners and thereby had broad market application prospects. SIGNIFICANCE: We have developed a ratiometric fluorescent probe based on the FRET platform for detecting sulfur dioxide derivatives and viscosity. QQC could not only successfully detect SO2 derivatives in food and water samples, but also be made into test strips for detecting HSO3-/SO32- solution. In addition, the probe was also used to detect viscosity changes caused by food thickeners. Therefore, this novel probe had significant value in food and environmental detection applications.
Assuntos
Corantes Fluorescentes , Dióxido de Enxofre , Humanos , Transferência Ressonante de Energia de Fluorescência , Viscosidade , Água , Células HeLaRESUMO
Fluoride ion is not only important for dental health, but also a contributing factor in a variety of diseases. At the same time, fluoride ions and cell viscosity are both important to the physiological environment of mitochondria. We developed a dual-response ratiometric fluorescent probe BDF based on Förster resonance energy transfer (FRET) and intramolecular charge transfer (ICT) mechanism for the detection of F- and viscosity. BDF has an outstanding intramolecular energy transfer efficiency of 97.7% and shows excellent performance for fluorine ion detection. In addition, when the system viscosity increases, the fluorescence emission intensity of BDF is greatly heightened, indicating the possibility of viscosity detection. Finally, based on the fluorescence properties of BDF, we used the probe to detect F- in the toothpaste sample and image exogenous fluoride ions in HeLa cells.
Assuntos
Transferência Ressonante de Energia de Fluorescência , Fluoretos , Humanos , Transferência Ressonante de Energia de Fluorescência/métodos , Corantes Fluorescentes , Células HeLa , Flúor , ViscosidadeRESUMO
This work presented a FRET-ICT based fluorescent probe (named NTC) composed of coumarin-benzothiazole as the acceptor and 4-nitrobenzo[c][1,2,5] oxadiazole (NBD) as the donor for the detection of SO2 derivatives in NIR. Probe NTC possessed superior performance including selectivity, quickly response toward SO32-/HSO3- and high energy transfer efficiency (94 %). The test strips provided a simple and effective tool in detecting the presence of bisulfite. Besides, NTC was applied to test the sulfur dioxide derivatives in food samples and cells.
Assuntos
Colorimetria , Corantes Fluorescentes , Humanos , Dióxido de Enxofre , Sulfitos , Transferência Ressonante de Energia de Fluorescência , Células HeLaRESUMO
Viscosity and sulfur dioxide levels are important factors to evaluate the changes of cell micro-environment because a series of diseases usually occur when they are abnormal. At present, dual-response probes that can detect both viscosity and sulfur dioxide are rare. Therefore, we developed a novel fluorescent probe CBN for simultaneous detection of sulfur dioxide and viscosity. Besides, probe CBN could target lysosome of which normal function will be disrupted by the abnormality of viscosity. Therefore, probe CBN has the potential to be served as an effective biological tool to monitor the intracellular micro-environment.
Assuntos
Corantes Fluorescentes , Dióxido de Enxofre , Humanos , Viscosidade , Lisossomos , Células HeLaRESUMO
The intracellular viscosity is an important parameter of the microenvironment and SO2 is a vital gas signal molecule. At present, some dual-response fluorescence probes for simultaneous measurements of viscosity and SO2 derivatives (HSO3-/SO32-) possessed poor water solubility. In this work, we developed a water-soluble fluorescence probe CIJ (0.0864 g/100 mL of water at 20 °C) for simultaneous measurements of viscosity and SO2 derivatives. CIJ exhibited a sensitive fluorescence enhancement to environmental viscosity from 0.97 to 28.04 cP based on a twisted intramolecular charge transfer mechanism and was applied to effective measurement of viscosity in vitro and in vivo. CIJ could also respond to SO2 derivatives with a low detection limit (44 nM) and a fast response time (5 min) based on the nucleophilic addition reaction. Furthermore, CIJ was applied to monitor SO2 derivatives in ratiometric response manner in living cells.
Assuntos
Transferência Ressonante de Energia de Fluorescência , Corantes Fluorescentes , Humanos , Solubilidade , Viscosidade , Sulfitos , Células HeLa , Água , Dióxido de EnxofreRESUMO
A novel fluorescence resonance energy transfer (FRET)-based ratiometric emission fluorescent probe AT was designed and developed in which the imidazo[1,5-α]pyridine was served as a FRET donor and tricyanofuran (TCF) as the FRET acceptor to detect SO32-/HSO3- based on the Michael addition reaction. Probe AT had a high energy transfer efficiency (95%) and a large pseudo-Stokes shift (259 nm) in EtOH/PBS buffer (5/5, v/v). It also possessed good selectivity and quick response to SO32-/HSO3-. There was good linearity between the ratio of fluorescence intensity (F499/F645) and the concentrations of SO32-/HSO3- in the ranges of 1.5-7.5 µM and 9-20 µM, with calculated detection limits (LOD) of 55 nM. In addition, the probe could also detect the concentrations of SO32-/HSO3- in real samples such as environmental water and sugar, allowing the probe to be used in a variety of applications.
Assuntos
Transferência Ressonante de Energia de Fluorescência , Corantes Fluorescentes , Piridinas , Dióxido de Enxofre , ÁguaRESUMO
Thiophenol (PhSH) is widely used in industry, however, it is extremely harmful to the environment and human health due to its high toxicity. In this work, we developed a new FRET-ICT-based ratiometric fluorescent and colorimetric probe (DMNP) for detecting PhSH. DMNP had an ultrahigh energy transfer efficiency (99.7%) and clear spacing of two emission peaks (133 nm). DMNP achieved a fast response to PhSH and exhibited drastic enhancement (over 2100 folds) of the fluorescence intensity ratio upon addition of PhSH. DMNP showed good linear response in the PhSH concentration ranges of 0.5-13 µM and 17.0-22.0 µM. Meanwhile, DMNP could also be applied to monitor PhSH in a variety of real water samples.
Assuntos
Transferência Ressonante de Energia de Fluorescência , Corantes Fluorescentes , Transferência Ressonante de Energia de Fluorescência/métodos , Corantes Fluorescentes/química , Humanos , Fenóis , Espectrometria de Fluorescência , Compostos de Sulfidrila , Água/químicaRESUMO
Sulfur dioxide derivatives (HSO3- and SO32-) play an important role in food preservative, antibacterial, antioxidant and other aspects, so it is urgent for us to develop more efficient detection methods to broaden their application in biochemical research and related disease diagnosis. Fluorescent probes are of particular interest because of their simplicity and high temporal and spatial resolution. Herein, we constructed a new near-infrared (NIR) fluorescence probe, CQC, composed of coumarin fluorophore and quinoline fluorophore, for detecting SO2 derivatives. The near-infrared emission probe CQC with a large Stokes shift (260 nm) not only kept the distance between the two emission peaks large enough (165 nm), but also had a particularly high energy transfer efficiency (99.5%), and was particularly sensitive to the detection of HSO3-/SO32- (LOD: 0.1 µM). The powerful probe CQC succeeded in real-time visualizing endogenous HSO3-/SO32- in living cells.
Assuntos
Quinolinas , Dióxido de Enxofre , Cumarínicos , Corantes Fluorescentes , Células HeLa , HumanosRESUMO
Though a number of on-off or off-on fluorescent probes have been developed for the detection of thiophenol by using its unique recognition groups, such as 2, 4-dinitrophenyl ether, 2, 4-dinitrophenyl sulfonamide, and 2, 4-dinitrophenyl sulfonate, up to now, there are few probes that can detect thiophenol by the proportional fluorescence signal. We developed a ratiometric fluorescent probe with coumarin pyridine derivative as fluorophore and 2, 4-dinitrophenyl ether moiety as the sensing unit which could be used to detect thiophenol derivatives by the aromatic nucleophilic substitution reaction. This probe (CPBPN) displayed significant change in fluorescence ratio (256 fold) to result in a more reliable analysis by self-calibration and a relatively low detection limit of 24 nM toward 4-methylthiophenol (MTP) within 30 min to achieve more sensitivity. Besides, the probe was also applied to detect the presence of thiophenol derivatives in actual water samples and fluorescence imaging in living cells. The present work is of great importance for monitoring environmental pollutants and studying their biological function.
Assuntos
Corantes Fluorescentes , Compostos de Sulfidrila , Imagem Óptica , Fenóis/análise , Compostos de Sulfidrila/análiseRESUMO
Two simple turn-on fluorescent probes, containing a benzothiazole and the 2,4-dinitrobenzenesulfonyl group, were designed for detecting H2S. Two probes exhibited good selectivity and high sensitivity, which were applied to detect the H2S in real water samples. Probe P2 with a positive charge had better solubility than probe P1 in water; therefore, probe P2 was successfully applied to detect both the endogenous and exogenous H2S in lysosomes of living HeLa cells.
Assuntos
Corantes Fluorescentes , Sulfeto de Hidrogênio , Benzotiazóis , Células HeLa , Humanos , Imagem Óptica , ÁguaRESUMO
A mild and high efficient method to prepare indolizines by two-component reaction with the acid as the catalyst was developed. In this reaction, a new ring efficiently formed in one-step reaction. A wide range of substrates could be applied and the desired products were obtained in 8-95% yields under metal-free conditions. Different indolizine derivatives (compounds 3a-3n) were synthesized by general conditions and microwave irradiation conditions, and compound 3a gave the best results with an isolated yield of 95% and 82%, respectively. The structures of synthesized compounds were characterized by spectral analysis, and compound 3m was confirmed by single crystal X-ray analysis. UV-vis absorption and fluorescence properties of these compounds were correlated with substituent groups on indolizine rings.
Assuntos
Indolizinas , Pirazóis , Catálise , Estrutura Molecular , Espectrometria de FluorescênciaRESUMO
This work presented a benzothiazole-based fluorescent probe for the detection of benzenethiol derivatives using 2, 4-dinitrobenzene moiety as a sensing unit. This probe (NCABT) was able to instantaneously respond to 4-methylbenzenethiol (MTP) within 5 min. In detecting MTP, this probe displayed a low limit of detection (49 nM). Furthermore, the probe has been proved to have the potential to detect benzenethiol derivatives with electron-donating group in real water samples.
Assuntos
Corantes Fluorescentes , Fenóis , Limite de Detecção , Compostos de SulfidrilaRESUMO
A new fluorescent probe (MBT) for the detection of 4-methylbenzenethiol (p-MePhSH) was developed by using 4-(benzo[d]thiazol-2-yl)-3-methoxyphenol as the fluorophore and 2,4-dinitrophenyl ether as the sensing moiety. Probe MBT displayed good selectivity toward p-MePhSH in DMSO/PBS buffer (5/5, v/v) solution and anti-interference over other competitive species via nucleophilic aromatic substitution. The fluorescence intensities of the probe responded p-MePhSH showed a 22-fold enhancement and good linearity with p-MePhSH concentration collected in the range of 0-15 µM. Moreover, the probe is sensitive to p-MePhSH and the limit of detection is 45 nM. The sensing mechanism of probe MBT was verified by high-resolution mass spectrometry and fluorescence lifetime. Furthermore, the probe was used to the detection of p-MePhSH in real water samples.
RESUMO
A deep-red emission and lipid droplets-targeted fluorescence probe (named ZFPy) for effective bioimaging of bisulfite was developed from flavone moiety and benzoindole derivative based on intramolecular charge transfer (ICT) and Förster resonance energy transfer (FRET) platform. ZFPy displayed promising fluorescence parameters including bright deep red fluorescence (615 nm), large Stokes shift (205 nm), extended emission window gap (140 nm), high absolute fluorescence quantum yield (4.1%) and stable emission signal output. In addition, ZFPy realized ratiometric fluorescence monitoring for SO2 derivatives with low detection limit (30 nM), preferable linearity, high sensitivity and selectivity. Interestingly, dual fluorophores (i.e. the donor moiety and 1,1,2,3-tetra-substituent-1H-benzo[e]indol-3-ium iodide moiety) released the same emission band about 475 nm to enhance the emission signal when ZFPy reacted with SO2 derivatives, to the best of our knowledge, this is the first synergetic FRET/ICT platform for fluorescence probe, which might effectively offer ZFPy a high sensitivity and low detection limit in the detection of SO2 derivatives. More importantly, ZFPy could image exogenous and endogenous SO2 derivatives in living HeLa, HepG2 and L-O2 cells with good biocompatibility and photostability. ZFPy also preferred to load on lipid droplets with high Pearson's coefficient (0.95).
Assuntos
Transferência Ressonante de Energia de Fluorescência , Gotículas Lipídicas , Corantes Fluorescentes , Humanos , SulfitosRESUMO
A new mitochondria-targeted fluorescent probe RBC, constructed using a coumarin moiety which was selected as the donor and a benzothiazole derivative as the acceptor, for SO2 derivatives (HSO3-/SO32-) was presented. The probe designed on a new FRET platform showed high selectivity and a low detection limit. Importantly, the probe could respond to HSO3-/SO32- within 35 s. Furthermore, the probe could target mitochondria and was successfully used for fluorescence imaging of endogenous bisulfite in HepG2 with low cytotoxicity, which significantly assisted in cancer diagnosis.
Assuntos
Benzotiazóis/farmacologia , Cumarínicos/farmacologia , Corantes Fluorescentes/farmacologia , Mitocôndrias/efeitos dos fármacos , Dióxido de Enxofre/análise , Benzotiazóis/química , Células Cultivadas , Cumarínicos/síntese química , Cumarínicos/química , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/química , Humanos , Concentração de Íons de Hidrogênio , Estrutura Molecular , Imagem Óptica , Tamanho da Partícula , Propriedades de SuperfícieRESUMO
A unique fluorescent probe (ZACA) for the monitoring of SO2 derivatives was developed from coumarin and benzoindoles based on FRET and ICT. ZACA exhibited an active emission signal, large Stokes shift, wide emission window distance, and high photostability. It also possessed many advantages in the ratiometric detection of HSO3-/SO32- including low detection limit and high selectivity and sensitivity. Importantly, ZACA was successfully applied in the ratiometric detection of endogenous HSO3-/SO32- in living cells with excellent cellular imaging capability (1 µM) and mitochondria-targeting ability (co-localization coefficient: 0.91).