Probe For Detection Of Hydrogen Sulfide Research Articles

A highly selective fluorescent probe for hydrogen sulfide detection in food, water, and living cells

Hydrogen sulfide (H2S)–an endogenously produced vapor–is essential for various physiological and neurological functions. However, abnormal H2S levels can negatively impact both the environment and food quality. Herein, a novel fluorescent probe, 2-(2-benzothiazol-2-ylvinyl)-5-diethylaminophenyl-2,4-dinitrobenzenesulfonate (BDD), has been designed and synthesized for the detection of H2S. BDD exhibits high selectivity, rapid response to H2S within 6minutes, and a low limit of detection (LOD = 0.87μM), with stable emission at pH range between 6 and 12. Moreover, BDD effectively recovers H2S in water samples with recovery rates ranging from 98.8% to 102.1% and monitors both internal and external H2S in HeLa cells. Additionally, BDD-loaded test strips are promising as a tool for measuring the freshness of raw meat on-site. These findings establish the foundation for significant advancements in detecting H2S in various environments, food sources, and biological systems.

Construction of an effective near-infrared fluorescence “turn-on” probe for hydrogen sulfide detection and imaging in living inflammatory cell and zebrafish models

Hydrogen sulfide (H2S) can act as a gaseous signaling mediator closely associated with inflammation development. In this work, we designed a fluorescence turn-on near-infrared (NIR) fluorescent probe CIT-H2S based on Intermolecular Charge Transfer (ICT) for the detection of H2S in living inflammatory cells and zebrafish. On this basis, a dicyanoisophorone fluorophore was chosen as the fluorescence signal reporting group of CIT-H2S, and an azide group was constructed as the recognition group of H2S. CIT-H2S is characterized by high selectivity and sensitivity for H2S over other interference species. The fluorescence intensity at 661 nm showed good linearity in the range of H2S concentration from 0 to 10 μM, with an excellent limit of detection (LOD) as low as 81.52 nM. Impressively, CIT-H2S has been visualized for detecting H2S in drug-induced inflammatory cell and zebrafish models, thus indicating that CIT-H2S is a robust tool with the ability to study the occurrence and development of hydrogen sulfide and inflammation.

A Highly Selective Fluorescent Probe for Hydrogen Sulfide and its Application in Living Cell.

A new Near-infrared fluorescent probe for hydrogen sulfide detection was synthesized by employing dicyanoisophorone based fluorescence dye as a fluorophore and methyl 3-(2-(carbonyl)phenyl)-2-cyanoacrylate group as the response unit. The Probe DCI-H2S showed a long emission wavelength (λem = 674nm). Based on the H2S-induced addition-cyclization of deprotecting methyl 3-(2-(carbonyl)phenyl)-2-cyanoacrylate group, the probe DCI-H2S showed high selectivity, sensitivity and response speed toward hydrogen sulfide under room temperature. These numerous advantages of the probe DCI-H2S make it to potentially detect endogenous hydrogen sulfide in living organisms.

A fast and specific near‐infrared fluorescent probe for hydrogen sulfide detection in aquaculture freshwater

AbstractThe content of Hydrogen sulfide (H2S) is one of the most important indicators of aquaculture water quality monitoring, which has a profound impact on the survival of aquatic animals and the income of aquaculture. Therefore, it's of great significance to develop an accurate and convenient detection method for the detection of hydrogen sulfide in aquaculture. Herein, using 2,4‐dinitrophenyl (DNP) ether as the detection group, a novel near‐infrared (NIR) fluorescent probe, X‐NO2, based on the hemicyanine fluorophore, was designed and synthesized for H2S detection in aquaculture. Accompanied by a noticeable color change from purple to blue, the probe X‐NO2 shows strong fluorescence at 685 nm when H2S mediates the thiolysis of DNP ether and release X‐OH. In 10 % DMSO‐PBS (pH=7.4,10 mM,v/v), the probe X‐NO2 shows high selectivity to H2S than other anions and some somebiologicalthiols, and strong anti‐interference capacity. Probe X‐NO2 also has short response time (within 3 min) and low detection limit (65 nM) towards H2S and has a stable performance over a wide pH range (6‐9) in hydrogen sulfide monitoring system. Moreover, probe X‐NO2 was used to determine the H2S levels in real water samples from aquaculture accurately and conveniently, which shows a good application prospect in the future.

A COX2-targeting cancer-specific fluorescent probe for hydrogen sulfide detection in living cells, Caenorhabditis elegans, and zebrafish.

A novel cyclooxygenase-2 (COX-2) targeted H2S-activated cancer-specific fluorescent probe, namely, COX2-H2S, was designed and synthesized, with naphthalimide as the fluorophore and indomethacin as the targeting group. This H2S-sensing probe was developed to differentiate tumor cells from normal cells and was tested in living cells, Caenorhabditis elegans (C. elegans), and zebrafish. The probe could successfully be used for imaging endogenous and exogenous H2S in living cells, demonstrating high sensitivity and specificity and strong anti-interference. COX2-H2S had the ability to not only discern cancer cells from normal cells but also specifically recognize 9L/lacZ cells from other glioblastoma cells (U87-MG and LN229). It could also be successfully applied for the fluorescent live imaging of H2S in both C. elegans and zebrafish.

Development of europium(III) complex fluorescent probe for hydrogen sulfide detection and its application in water samples.

Hydrogen sulfide (H2 S) is a crucial endogenous signaling component in organisms that is involved in redox homeostasis and numerous biological processes. Modern medical research has confirmed that hydrogen sulfide plays an important role in the pathogenesis of many diseases. Herein, a fluorescent probe Eu(ttbd)3 abt based on europium(III) complex was designed and synthesized for the detection of H2 S. Eu(ttbd)3 abt exhibited significant quenching for H2 S at long emission wavelength (625 nm), with rapid detection ability (less than 2min), high sensitivity [limit of detection (LOD) = 0.41 μM], and massive Stokes shift (300 nm). Additionally, this probe showed superior selectivity for H2 S despite the presence of other possible interference species such as biothiols. Furthermore, the probe Eu(ttbd)3 abt was successfully applied to detect H2 S in water samples.

Red-emitting fluorescent probe for hydrogen sulfide detection and its applications in food freshness determination and in vivo bioimaging.

We report the development of a red-emitting fluorescence probe (XDS) for hydrogen sulfide (H2S) detection in biosystems, real-world food samples, and application of this probe for monitoring of H2S production during food spoilage. The XDS probe is developed by coupling of coumarin derivative to rhodanic-CN through a H2S responsive CC bond. Remarkable fluorescence quenching of XDS is observed as a result of the response to H2S. Semi-quantitative detection of H2S in three real-world water and two beer samples and monitoring of H2S production during food spoilage in real-time by "naked-eye" and smartphone colorimetric analysis are then achieved using XDS as the probe. Moreover, XDS is low toxicity, allowing it being used for visualizing endogenous and exogenous H2S in vivo in a mouse model. It is expected that the successful development of XDS could provide an effective tool for investigating the roles of H2S in biomedical system and for future food safety evaluation.

A New Fluorescent Probe for Hydrogen Sulfide Detection in Solution and Living Cells.

Since Hydrogen Sulfide (H2S) was recognized as a gas transmitter, its detection and quantification have become a hot research topic among chemists and biologists. In this area, fluorescent probes have shown great advantages: fast and strong response, low detection limit and easy manipulation. Here we developed a new fluorescent probe that detected H2S selectively among various bioactive and inorganic salts. This probe was based on the core structure of fluorescein and reacted with H2S through azide-reduction. Great linearity was achieved correlating fluorescence intensity and H2S concentrations in solution. The detection of H2S in cancer cells was also achieved.

Novel 3RAX-based fluorescent probe for hydrogen sulfide detection and photodynamic therapy

As an important signalling molecule, hydrogen sulfide (H2S) has crucial functions in physiological and pathological processes. Abnormal levels of H2S are generally associated with many diseases, so the realization of biological real-time monitoring of H2S in the body is critical. So far, many excellent H2S fluorescent probes have been developed and used, but most of them have only a single function with only a diagnostic function but no therapeutic effect in cancer treatment. We designed and synthesized a novel methylene violet 3RAX derivative F3 with methylene violet as the fluorescent group and 2,4-dinitrobenzenesulfonamide as the recognition group. F3 was shown to be a turn-on fluorescent probe with high selectivity and sensitivity to H2S (LOD: 23 nM) at a 623 nm emission wavelength. In addition, F3 could also be used as a promising photosensitizer to generate singlet oxygen, which showed satisfactory photodynamic therapy (PDT) effects in cervical cancer cells (IC50 for HeLa cells = 9 μM).

A novel near-infrared fluorescence probe for hydrogen sulfide detection and application in cell and mice imaging

We presented here a novel near-infrared fluorescent probe based on 2-(2′-hydroxyphenyl)benzothiazole -dicyanoisophorone as fluorophore and 2,4-dinitrobenzenesulfonyl moiety as detection functionalized group for the discrimination of hydrogen sulfide (H2S). Probe L exhibited good specificity and sensitivity “turn on” response at 720 nm with a large Stokes shift (155 nm), rapid response (<60 s) and low detection limit (3.15 × 10−7 M), which also could be identified by the naked eyes. Moreover, probe L was successfully used to image exogenous/endogenous H2S in cells and mice, which demonstrated its potential applications in living systems.

A multifunctional BODIPY based fluorescent probe for hydrogen sulfide detection and photodynamic anticancer therapy in HCT116 colon cancer cell

Development of multifunctional probes that can be simultaneously utilized for both efficient hydrogen sulfide detection and photodynamic therapy in cancer cells is in high demand but remains worldwide challenge. Herein, a fluorescent probe DB2T based on a BODIPY structure for H2S fluorescence “turn-on” detection together with light sensitive anticancer capacity has been designed and synthesized. The probe DB2T features high selectivity towards H2S, excellent low detection limit (6.39 nM), and good biocompatibility. Importantly, the probe DB2T has been satisfactorily applied in fluorescence imaging of exogenous H2S in zebrafish, and successfully employed in fluorescence imaging of endogenous H2S in HCT116 cell and tumor tissues. Moreover, evaluation of the phototherapy effect demonstrates that the probe DB2T performs well as a photosensitizer for photodynamic ablation of HCT116 cancer cells upon white light irradiation. This work should facilitate significant advances in rational design of fluorescence systems for H2S detection and even in the diagnosis and treatment of H2S related diseases.

A cancer cell-specific benzoxadiazole-based fluorescent probe for hydrogen sulfide detection in mitochondria.

The present work describes the design and biological applications of a novel colorimetric and fluorescence turn-on probe for hydrosulfide detection. The probe was designed to introduce hemicyanine as the fluorescent skeleton and 7-nitro-1,2,3-benzoxadiazole as the recognition site. The optical properties and responses of the probe towards HS-, anions and some biothiols indicate an impressively high selectivity of the probe towards HS- such that it can be effectively used as an indicator for monitoring the level of HS- in living cells. In biological experiments using the probe, the H2S levels are found to be higher in cancer cells than in normal cells. In addition, the probe is shown to specifically and rapidly detect endogenous H2S, which is produced primarily in the mitochondria of cancer cells, as demonstrated by a co-localization experiment using specific trackers for the detection of cellular organelles in pharmacological inhibition or stimulation studies, without any significant cytotoxic effects. Thus, the results of the chemical and biological experiments described herein demonstrate the potential of this novel probe to specifically, safely, and rapidly detect H2S to distinguish cancer cells from normal cells by targeting it specifically in mitochondria.

A near-infrared naphthofluorescein-based fluorescent probe for hydrogen sulfide detection

A simple naphthofluorescein-based probe was designed and synthesized by a two-step method. As expected, there was a good linear relationship between fluorescence intensity (680 nm)/absorbance (640 nm) and H2S concentration in the range of 2.00–10.0 μM with a detection limit of 0.50 μM/0.10 μM (S/N = 3). This probe was applied to monitor H2S concentration in red wine samples. Furthermore, it was successfully used to image exogenous H2S in living Hela cells, indicating its potential application in biology and medicine.

A quaternary ammonium modified fluorescent probe for hydrogen sulfide detection in living cells

Azide-reduction based fluorescent probes are one of the most important methods for H2S detection. However, low water solubility and low sensitivity are common problems encountered by such probes. Herein, five azide-reduction based probes with corresponding hydrophilic moieties (hydroxyl, tertiary amine, and quaternary ammonium) attached were rationally designed and synthesized. After a comparative study of their spectral properties, we found that the quaternary ammonium modified probe H3 showed the total solubility in water and the best reactivity to H2S as well as the lowest detection limit, indicating that the quaternary ammonium moiety not only improved the solubility of the probe, but also had a significant sequestration effect for HS−. A further application of H3 in HeLa cells was also carried out and validated its potential for biological imaging.

A Visible Colorimetric Fluorescent Probe for Hydrogen Sulfide Detection in Wine.

A new efficient and practical fluorescent probe 6-(benzo[d]thiazol-2-yl)naphthalen-2-yl-thiophene-2-carboxylate (probe 1) was synthesized to detect hydrogen sulfide (H2S). The addition of H2S caused the solution of probe 1 to change from colorless to yellow, and the solution of probe 1 changes to different colors with respect to different concentrations of H2S. Importantly, probe 1 could help detect H2S efficiently by a distinct color response as a visible detection agent. Probe 1 reacted with various concentrations of H2S (0–200 μM), and the detection limit for H2S was 0.10 μM. Particularly, probe 1 can be applied as a sensor to detect H2S accurately in wine samples.

Highly selective and rapidly responsive fluorescent probe for hydrogen sulfide detection in wine

A new fluorescent probe 6-(2, 4-dinitrophenoxy)-2-naphthonitrile (probe 1) was designed and synthesized for the selective detection of hydrogen sulfide (H2S). The addition of H2S to a solution of probe 1 resulted in a marked fluorescence turn-on alongside a visual color change from colorless to light yellow. Importantly, this distinct color response indicated that probe 1 could be used as a visual sensor for H2S. Moreover, probe 1 was successfully used as a signal tool to determine the H2S levels in beer and red wine.

A visible light excitable colorimetric and fluorescent ESIPT probe for rapid and selective detection of hydrogen sulfide

In this paper, a visible light excitable ESIPT probe was developed, which was found to be a very promising colorimetric and fluorescent sensor for rapid and selective detection of hydrogen sulfide in aqueous solution. The sensing mechanism and the application of this probe for hydrogen sulfide detection in biological serum and in simulated wastewater samples were investigated.

A highly selective turn-on near-infrared fluorescent probe for hydrogen sulfide detection and imaging in living cells

We have described a turn-on near-infrared fluorescent probe Cy-NO(2) based on nitro group reduction for intracellular H(2)S detection. The probe employs cyanine dye as a fluorophore, and is equipped with a nitro group as a fluorescent modulator. It is readily employed for assessing intracellular H(2)S level changes, and confocal imaging is achieved successfully.