Sulfur Dioxide Derivatives Research Articles

A novel fluorescent probe for fast detection of sulfur dioxide derivatives in water, soil, food samples and its applications in biological imaging

Sulfur dioxide (SO2) has a wide range of applications in food additives and industrial production, and it is one of the main substances that form acid rain, causing serious harm to ecosystems and human health. Hence, it is necessary to construct an effective tool to quickly and accurately detect SO2 derivatives in environmental, food, and biological samples. In this study, fluorescent probe NPMQ was built to detect SO2 derivatives from nopinone with the merits of superior water solubility, high sensitivity (12nM), excellent specificity, large Stokes shift (180nm), and rapid response time (within 5s). NPMQ was used to qualitatively and quantitatively detect SO2 derivatives in environmental water, soil and food samples. In addition, an electrospinning film was prepared with the probe NPMQ to image SO2 derivatives, and test strips are capable of rapidly, sensitively, and selectively detecting SO2 derivatives with the naked eye. Moreover, the probe NPMQ was used to visualize endogenous SO2 derivatives in Arabidopsis thaliana under Cd2+ stress. Furthermore, the probe NPMQ was employed to image exogenous and endogenous SO2 derivatives in living Hela, HepG-2 cells, and zebrafish. This study develops an effective tool for monitoring SO2 derivatives in the environmental, food, and biological systems.

A ratiometric fluorescent sensor based on dual-emitting carbon dots for the rapid detection of sulfite

Sulfur dioxide (SO2) derivatives are typically employed as antioxidants in food and pharmaceutical processing. However, excessive sulfite intake could trigger serious health problems. Hence, it is urgent to establish a rapid and effective system for monitoring SO2. This study adopted a one-step hydrothermal method to synthesize dual-emitting nitrogen-doped carbon quantum dots (CECDs) and developed a ratiometric sensor for sulfite using CECDs-Cr (VI) composites. The emission intensity ratio (I440/I500) of the CECDs-Cr (VI) composites increased considerably with the addition of HSO3−. A method based on the ratiometric sensor was established for SO2 derivatives with advanced efficiency and excellent linearity over a broad concentration range of 0–500 μM (R2 = 0.9946). Four medicine-food homology materials (MFHMs) fumigated with sulfur have been accurately detected using this approach. Furthermore, a portable test tube was prepared to achieve rapid and semi-quantitative detection of SO2 residues and applied to real samples. This work presents an effective approach to develop a rapid on-site detection platform for sulfite residues in food and pharmaceuticals.

A near-infrared ratiometric fluorescent probe for the sensing and imaging of sulfur dioxide derivatives in living systems

As a reactive sulfur species, sulfur dioxide (SO2) and its derivatives play crucial role in various physiological processes, which can maintain redox homeostasis at normal levels and lead to the occurrence of many diseases at abnormal levels. So, the development of a suitable fluorescent probe is a crucial step in advancing our understanding of the role of SO2 derivatives in living organisms. Herein, we developed a near-infrared fluorescent probe (SP) based on the ICT mechanism to monitor SO2 derivatives in living organisms in a ratiometric manner. The probe SP exhibited excellent selectivity, good sensitivity, fast response rate (within 50 s), and low detection limit (1.79 µM). In addition, the cell experiment results suggested that the SP has been successfully employed for the real-time monitoring of endogenous and exogenous SO2 derivatives with negligible cytotoxicity. Moreover, SP was effective in detecting SO2 derivatives in mice.

A novel theranostic strategy for myocardial infarction through neutralization of endogenous SO2 using an endoplasmic reticulum-targeted fluorescent probe

Myocardial infarction (MI), one of the leading causes of death worldwide, urgently needs further understanding of the pathological process and effective therapies. SO2 in endoplasmic reticulum in several cardiovascular diseases has been reported to be particularly important. However, the role of endogenous SO2 in endoplasmic reticulum in treating myocardial infarction is still ambiguous and needs to be elucidated. Herein, we developed TPA-HI-SO2 as the first endoplasmic reticulum-targeting fluorescent agent for specific imaging and detection of sulfur dioxide derivatives both in vitro and in vivo. TPA-HI-SO2 shows a highly sensitive and selective response to SO2 derivatives over other anions in aqueous solution with a satisfactory response time and detection limit. Furthermore, TPA-HI-SO2 decreased the SO2 concentration in H9C2 cells treated with H2O2 and in an MI mouse model. Most importantly, TPA-HI-SO2 protects H9C2 cells from H2O2-induced apoptosis and obviously protects against myocardial infarction in vivo through neutralization of endogenous SO2. Taken together, we developed the first ER-targeting ratiometric fluorescent probe for endogenous SO2 with excellent biocompatibility, high selectivity and sensitivity in this paper. More importantly, we demonstrated an obvious increase of the endogenous SO2 concentration in a myocardial infarction mouse model for the first time, which suggests that neutralization of endogenous SO2 in endoplasmic reticulum could be a promising therapeutic strategy for myocardial infarction.

NBD-based colorimetric and ratiometric fluorescent probe in NIR for bisulfite

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.

A ratiometric fluorescent probe based on the FRET platform for the detection of sulfur dioxide derivatives and viscosity

BackgroundSulfur 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. ResultsIn 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. SignificanceWe 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.

A near-infrared AIE fluorescent probe for accurate detection of sulfur dioxide derivatives and visualization of fingerprints

In most biophysiological processes, sulfur dioxide (SO2) is an important intracellular signaling molecule that plays an important role. The change of SO2 in cells are closely related to various diseases such as neurological disorders and lung cancer, so it is necessary to develop fluorescent probes with the ability to accurately detect SO2 during physiological processes. In this work, we designed and synthesized a multifunctional fluorescent probe TIS. TIS has excellent properties such as near-infrared emission, large stokes shift, excellent SO2 detection capabilities, low detection limit, high specificity and visualization of color change before and after reaction. Simultaneously, TIS has low cytotoxicity, good biocompatibility, clear cell imaging capability and mitochondrial targeting ability. In addition, the ability of TIS to be applied to different material surfaces for latent fingerprint fluorescence imaging was also explored. TIS provides an excellent method for the accurate detection of SO2 derivatives and shows great potential applications in near-infrared cellular imaging and latent fingerprint fluorescence imaging.

A near-infrared fluorescent probe for rapid and on-site detection of sulfur dioxide derivative in biological, food and environmental systems

Emission of toxic gaseous sulfur dioxide (SO2) and its derivative bisulfite (HSO3–) from various industrial applications, like food processing, transportation, and the coking process, has raised substantial concerns regarding environmental quality and public health. The probes for specific and sensitive detection of SO2 derivatives plays an essential role in their regulation, and ultimately mitigating their environmental and health implications, but the one that can detect SO2 derivatives onsite by end users remains limited. Herein, we report a new near-infrared fluorescence probe (SL) for rapid and onsite detection of SO2 derivative, HSO3– in industrial wastewater, food samples and for sensing its interaction with biological organisms. The SL is developed through coupling of quinolinium and coumarin moiety through an electron deficit CC bond that can specifically react with HSO3− via a Michael addition. By recording the blue shift of absorption and emission spectra, SL can sensitively detect HSO3– (limit of detection, 38 nM) in aqueous solution within 40 s SL is biocompatible, can be used for evaluating toxicity of SO2 derivatives in living organisms. The preparation of SL-stained test paper allows the colorimetric/fluorometric analysis for quantification of HSO3– onsite in food, river and coking wastewater samples using a smartphone. The successful development of SL not only provides a new tool to investigate HSO3– in biological, food and environmental systems, but also potentially promotes the application of fluorescence technique for rapid and onsite analysis of real-world samples by end users.

A Mitochondria‐Targeted Fluorescent and Colorimetric Probe for Sulfur Dioxide Derivatives and Hydrogen Peroxide in Live Cells

AbstractThe abnormal fluctuations of sulfur dioxide (SO2) and its derivatives are closely associated with various physiological and pathological progresses in biological systems. Herein, we have developed two fluorescent and colorimetric probes based on a hemicyanine dye for the detection of SO2 derivatives and hydrogen peroxide (H2O2) in vitro and live cells. The response mechanisms involve an SO2‐derivative‐mediated nucleophilic addition reaction to the double bond and subsequent H2O2‐promoted elimination of bisulfite. As well as having excellent photophysical properties, the probe with higher fluorescence efficiency is further applied for live cell imaging, and it is found that it can solely accumulate in mitochondria and track SO2 derivatives and H2O2 in live cells.

Development of a Ratiometric Fluorescent Probe with Zero Cross-Talk for the Detection of SO2 Derivatives in Foods and Live Cells.

Sulfur dioxide (SO2) derivatives are extensively utilized as both a preservative for foods and an active gaseous signal molecule in various physiological and pathological processes, but their excessive intake would bring harmful effects on human health; so, the determination of SO2 derivatives is of great importance. Herein, we developed a ratiometric fluorescent probe named 2-(2'-hydroxyphenyl)benzothiazole-3-ethyl-1,1,2-trimethyl-1H-benzo[e]indolium (HBT-EMBI) by introducing a hemicyanine unit of EMBI to an HBT group for the detection of SO2 derivatives via an excited-state intramolecular proton transfer (ESIPT) and intramolecular charge transfer (ICT) effects. The probe displays some advantages, such as a colorimetric change from purple to colorless, a ratiometric fluorescence with zero cross-talk, and a remarkably large emission shift (Δλ = 164 nm) under a single-wavelength excitation. Accordingly, the probe HBT-EMBI has been successfully employed for the colorimetric and ratiometric determination of SO2 derivatives in real food samples and the quantitative visualization of SO2 derivative variations in HepG2 cells.

Sulfur dioxide derivatives aggravated ovalbumin-induced asthma through targeting TRPV1 and tight junctions

This study aimed to investigate the effects of sulfur dioxide (SO2) derivatives on asthma induced by ovalbumin (OVA). Sprague Dawley rats were sensitized to and challenged with OVA and SO2 derivatives (NaHSO3 and Na2SO3, 1:3M/M) to establish 28-day (short-term) and 42-day (long-term) asthma models. Exposure to SO2 derivatives aggravated asthma and hence, promoted lung injury in OVA-induced asthma. In addition, it upregulated the protein expression of TRPV1 and downregulated the expression of tight junctions (TJs). These changes were dose-dependent and were more pronounced in the presence of a high concentration of SO2 derivatives. In vitro, SO2 derivatives also increased the calcium influx and TRPV1 protein expression, and decreased TJ expression. Besides, no significant difference in the TJ expression was found between the WT and TRPV1-/- mice. The underlying mechanism might be related to regulating the effects of TRPV1 and TJs.

A dual-response fluorescent probe for SO2 and viscosity in lysosomes

As a signal molecule, SO2 plays an important role in the process of cell metabolism. The abnormal level of sulfur dioxide will induce many diseases of human body. Viscosity is an important index of lysosome. Abnormal lysosome viscosity can also lead to many diseases. Therefore, we have developed a new fluorescence probe PAPD for simultaneous imaging of sulfur dioxide derivatives and lysosomal viscosity. The probe realizes rapid detection of HSO3− based on Michael addition reaction mechanism. At the same time, with the increase of viscosity, intramolecular rotation is inhibited, thus the probe shows sensitive fluorescence enhancement. In addition, the results of the co-localization experiments show that PAPD has good lysosomal targeting ability. Further studies show that PAPD can be used as a dual-responsive fluorescence probe for SO2 and viscosity in lysosomes.

An effective LDs-targeted ratiometric fluorescent probe for sulfur dioxide derivatives

In this work, a novel FRET-based fluorescent probe (named CBC) was developed to detect bisulfite with outstanding selectivity by ratiometric method. Probe CBC exhibited excellent sensitivity toward HSO3− within 1 equivalent. The cell imaging of CBC indicated that it could detect exogenous and endogenous bisulfite with excellent photostability and low cytotoxicity. What's more, probe CBC realized the lipid droplet targeting. Therefore, probe CBC has the capacity to be used as a biological tool to monitor the bisulfite changes in vivo.

Water-soluble ratiometric fluorescent probes for exogenous and endogenous sulfur dioxide derivatives

Abnormal SO2 derivatives level induces mitochondrial and lysosomal dysfunction, which is associated with a variety of diseases. Therefore, it is imperative to develop fluorescent probes which are suitable for detection of SO2 derivatives in biological systems. Herein, we developed two new ratiometric fluorescent probes, MByn and HByn, which can respond to HSO3− in PBS buffer solution accurately and rapidly on basis of Michael addition reaction. After addition of HSO3−, ratiometric response signal increases by 5 folds, accompanied by a macroscopic change of fluorescence color. What's more, the two novel fluorescent probes MByn and HByn exhibited low detection limit (LOD = 0.96/0.79 μM), good photostability and low cytotoxicity. Cell imaging experiments showed that MByn and HByn were able to localize mitochondria and lysosomes accurately and detect both exogenous and endogenous SO2 derivatives in living cells.

A novel colorimetric and red-emitting fluorescent probe based on benzopyrylium derivatives for selective detection and imaging of SO2 derivatives in cells and zebrafish

Abnormal levels of endogenous sulfur dioxide in organisms will cause cardiovascular, respiratory and neurological diseases. Therefore, the development of an effective detecting method for real-time, quantitative detection of sulfur dioxide derivatives in organisms is of great importance in physiological and pathological aspects. In this work, a red-emitting SO2 fluorescent probe based on benzopyrylium derivatives were designed and synthesized to specifically detect SO2 derivatives by nucleophilic addition of unsaturated carbon-carbon double bonds. The probe is characterized with rapid response, “naked eye” visualization, broad detection range and high sensitivity (8.1 μM) for SO2 derivatives. In addition, it has been applied to track the dynamic, real-time, visual detection of exogenous and endogenous SO2 in cells, and imaging of exogenous SO2 derivatives in zebrafish.

Dual-response and lysosome-targeted fluorescent probe for viscosity and sulfur dioxide derivatives

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.

Reversible Near-Infrared Fluorescent Probe for Rapid Sensing Sulfur Dioxide and Formaldehyde: Recognition and Photoactivation Mechanism and Applications in Bioimaging and Encryption Ink.

A novel near-infrared (NIR) fluorescent Probe 1 was successfully developed for the reversible detection of sulfur dioxide derivatives and formaldehyde. The purple solution of Probe 1 faded to colorless in 1.8 s with the addition of HSO3-. Meanwhile, its fluorescence signal disappeared instantaneously with a 39 nM detection limit. The probe exhibited excellent selectivity toward HSO3- over other potential interfering agents. Then, its absorption and fluorescence bands were able to effectively recover in response to formaldehyde. Remarkably, this reverse process was able to accelerate 84 times under UV light in 122 s and achieved a recovery rate of 98% by UV light, the photoactivation mechanism was fully determined by HRMS and theoretical calculation. Furthermore, we demonstrated that Probe 1 was successfully applied for the detection of sulfur dioxide derivatives and formaldehyde in living cells and data encryption.

An imidazo[1,5-α]pyridines-based ratiometric fluorescent probe for sensing sulfur dioxide derivatives in real samples based on a FRET mechanism

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.

Mitochondria-targetable colorimetric and far-red fluorescent sensor for rapid detection of SO2 derivatives in food samples and living cells

Sulfur dioxide (SO2) derivatives are intertwined with many physiological and pathological processes in living systems, and excess intake of them are associated with various diseases. Herein, we have rationally constructed a novel colorimetric and far-red fluorescent probe for HSO3− based on a rhodamine analogue skeleton bearing a 3-quinolinium carboxaldehyde moiety. The novel probe exhibited a significant far-red fluorescence “Turn-on” response to HSO3−, along with obvious color change from reddish to purple via the specific 1,4-nucleophilic addition reaction of HSO3− with the quinolinium moiety in 3-(4-(2-carboxyphenyl)-7-(diethylamino)chromenylium-2-yl)-1-methylquinolin-1-ium hypochlorite trifluoromethanesulfonate (AQCB). The AQCB had excellent water-solubility, and presented rapid response (<15 s),highsensibility(LOD = 49 nM) and selectivity toward HSO3−. In addition, the probe was able to detect the content of HSO3− in food samples with satisfactory results. Furthermore, the probe possessed good cell membrane and could be successfully applied for imaging HSO3− in the mitochondria of living cells.

A quinoline-coumarin near-infrared ratiometric fluorescent probe for detection of sulfur dioxide derivatives

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.