A ratiometric fluorescent probe for rapid and specific detection of hypochlorite

Hypochlorite (ClO⁻), as a kind of essential reactive oxygen species, plays a crucial role in vitro and in vivo. Here, a ratiometric fluorescent probe ( TPAM ) was designed and constructed for sensing ClO⁻ based on substituted triphenylamine and malononitrile, which exhibited obvious colour transfer from orange to colourless under daylight accompanied by noticeable fluorescence change from red to green in response to ClO⁻. TPAM could effectively monitor ClO⁻ with the merits of fast response, excellent selectivity, high sensitivity and a low detection limit of 0.1014 μM. ¹H NMR, mass spectra and theoretical calculations proved that ClO⁻ caused the oxidation of the carbon–carbon double bond in TPAM , resulting in compound 1 and marked changes in colour and fluorescence. In addition, TPAM was utilized for imaging ClO⁻ in living cells successfully with good photostability and biocompatibility.     

Rapid and visual detection for hypochlorite of an AIE enhanced fluorescence probe

In this paper, a new ‘turn‐on' fluorescence probe for the rapid, sensitive, and visual detection of hypochlorite is reported. The push–pull type trianiline–tricyanofuran‐based fluorescent probe was prepared using a condensation reaction between tricyanofuran and the thiophene–trianiline derivative that had high quantum yields and showed aggregation‐induced emission enhanced properties. Upon exposure to hypochlorite, prominent fluorescence enhancement of the probe was observed via the release of the fluorophore from the probe. The probe showed a ratiometric absorption change at 315 nm and 575 nm. Importantly, the probe showed an excellent detection limit for hypochlorite at 1.2 × 10^?7 M in solution and it was successfully applied for monitoring hypochlorite in waste water by test strip. This work reports a new fluorescence analytical sensing method for hypochlorite that has potential practical value in environmental monitoring and biological discrimination.     

A colorimetric fluorescent probe for rapid and specific detection of nitrite

The method of fluorescent probes has been an important technique for detection of nitrite (NO₂^?). As an important inorganic salt, excessive nitrite would threaten humans and the environment. In this paper, a colorimetric fluorescent probe P‐N (1,2‐diaminoanthraquinone) with rapid response and high selectivity, which could detect NO₂^? by visual colour changes and fluorescence spectroscopy is presented. The probe P‐N solution (pH 1) changed from pink to colourless with the addition of NO₂^? and fluorescence intensity at 639 nm clearly decreased. Good linear exists between fluorescence intensities and NO₂^? concentrations for the range 0–16 μM, and the detection limit was 54 nM (based on a 3σ/slope). Moreover, probe P‐N could also detect NO₂^? in real water samples, and results were all satisfactory. Probe P‐N shows great practical application value for detecting NO₂^? in the environment.     

A dual-function fluorescent probe for the detection of pH values and formaldehyde

A dual-function fluorescent probe (Probe 1) was developed in this work for the separate detection of pH value and formaldehyde (HCHO). Probe 1 could recognize HCHO and the pH value from the amino group. The colour of the probe solution was changed from grey blue to light blue with the increase in the pH value, and luminous intensity became larger with the increase in formaldehyde concentration. The curve function relationship between fluorescence intensity and the pH value was also determined. A smartphone containing a colour detector for imaging was used to record the values of the three primary colours (R value, G value, and B value) for the probe solution in formaldehyde. Importantly, there was a linear functional relationship between the B*R/G value with HCHO concentration. Therefore, the probe could be used as a rapid tool for the detection of formaldehyde. More importantly, Probe 1 was successfully used to detect formaldehyde in an actual distilled liquor sample.     

A highly selective colorimetric and long‐wavelength fluorescent probe for the detection of Hg2+

Currently, the fluorescent probe is an important method for detecting heavy metal ions, especially mercury ion (Hg²⁺), which is harmful to the health of humans and the environment due to its toxicity and extensive use. In this paper, we designed and synthesized a colorimetric and long‐wavelength fluorescent probe Hg‐P with high sensitivity and excellent selectivity, which could detect Hg²⁺ by the changes of visual color, fluorescence and absorption spectroscopy. With the addition of Hg²⁺ to probe Hg‐P solution, its color changed from yellow to pink, and showed a 171 nm red‐shifted absorption spectrum. Probe Hg‐P was used in real water and soil solution samples to detect Hg²⁺, and the result is satisfactory. Therefore, this new probe shows great value and application in detecting Hg²⁺ in the environment.     

A coumarin‐based fluorescent turn‐on probe for detection of biothiols in vitro

A novel fluorescent probe (CA‐N) was designed and synthesized for detection of biothiols. CA‐N displayed a strong fluorescence in the presence of biothiols with high sensitivity, and the mechanism for detection biothiols was based on the Michael addition reaction of a thiol group to α,β‐unsaturated ketones. CA‐N showed low detection limit for cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), which were calculated as 3.16, 0.19 and 5.15 μM, respectively. At the same time, CA‐N exhibited high selectivity toward biothiols compared with other biological amino acids. In vitro cell experiments proved that CA‐N had no cytotoxicity, high cell permeability and could be employed in living cell imaging for biothiols. Copyright © 2015 John Wiley & Sons, Ltd.     

A novel viscosity-sensitive fluorescent probe for monitoring the changes of mitochondrial viscosity

As a fundamental physical parameter, viscosity influences the diffusion in biological processes. The changes in intracellular viscosity led to the occurrence of relevant diseases. Monitoring changes in cellular viscosity is important for distinguishing abnormal cells in cell biology and oncologic pathology. Here, we devised and synthesized a viscosity-sensitive fluorescent probe LBX-1 . LBX-1 showed high sensitivity, providing a large Stokes shift as well as an enhancement in fluorescent intensity (16.1-fold) from methanol solution to glycerol solution. Furthermore, the probe LBX-1 could localize in mitochondria because of the ability of the probe to penetrate the cell membrane and accumulate in mitochondria. These results suggested that the probe could be utilized in monitoring the changes in mitochondrial viscosity in complex biological systems.     

A colorimetric and ratiometric fluorescent probe for sulfite based on an intramolecular cleavage mechanism

A colorimetric and ratiometric fluorescent sulfite probe, the levulinate of 4‐hydroxynaphthalimide, was successfully synthesized from 4‐hydroxy‐naphthalimide and levulinic acid. Through sulfite‐mediated intramolecular cleavage, the probe was converted into 4‐hydroxynaphthalimide, which when excited at 450 nm, displayed a large Stokes shift due to the intramolecular charge transfer process. The probe exhibited high selectivity and sensitivity towards sulfite over other typical anionic species (F^–, Cl^–, Br^–, I^–, HPO₄^2–, SO₄^2–, NO₃^–, AcO^–, ClO₄^–, HCO₃^–) in HEPES‐buffered solution (25 mm , pH 7.4, 50% acetonitrile, v/v). Copyright © 2013 John Wiley & Sons, Ltd.     

A highly selective colorimetric and fluorescent dual‐modal probe for the rapid determination of fluoride anions

In this work, 4‐(p ‐hydroxybenzylidenehydrazino)‐N ‐butyl‐1,8‐naphthalimide ( 1 ) has been designed and synthesized as a colorimetric and fluorescent dual‐modal probe for F^?. Compound 1 immediately detected inorganic fluoride salts using UV /v is absorption and fluorescence spectroscopy methods, and served as a ‘naked‐eye’ indicator for F^? with high selectivity and sensitivity. Both the absorption and fluorescence spectra show excellent linearity with the concentration of F^?. Real‐life applications demonstrated that our proposed analytical system provided a satisfactory method for the determination of F^?. In addition, the reaction mechanism of deprotonation was confirmed by ¹H NMR.     

A novel fluorescent probe with large Stokes shift for the detection of viscosity changes and its imaging in living cells

As an important cellular microenvironmental parameter, viscosity could reflect the status of living cells. Small molecular fluorescent probes are a vital tool to measure the change of viscosity in living cells. A novel fluorescence probe ZL-1 with a large Stokes shift (in methanol it reached to 153 nm and in glycerol it reached to 125 nm) and excellent sensitivity toward viscosity was developed. The sharp enhancement of the emission intensity for the probe ZL-1 from low viscous methanol to high viscous glycerol indicated that the probe ZL-1 could respond to the viscosity variations. Moreover, the probe ZL-1 has been successfully utilized to detect of the viscosity variations in living cells.     

A deep-red xanthene-based highly sensitive fluorescent probe for detection of hypochlorite

As an oxidant, deodorant and bleaching agent, the hypochlorous acid (HClO) and hypochlorite (ClO⁻) are widely used in corrosion inhibitors, textile dyes, pharmaceutical intermediates and in our daily lives. However, excess usage or aberrant accumulation of ClO⁻ leads to tissue damage or some diseases and even cancer. Therefore, it is necessary to develop a fluorescent probe that specifically identifies ClO⁻. In this article, we synthesized a deep-red xanthene-based fluorescent probe (XA-CN). The strong electron deficient group dicyano endows the probe XA-CN deep-red fluorescent emission with high solubility, selectivity and sensitivity for ClO⁻ detection. Studies showed that the probe demonstrated turn-off fluorescence (643 nm) at the presence of ClO⁻ in dimethylsulfoxide/phosphate-buffered saline 1:1 (pH 9) solution with a limit of detection of 1.64 μM. Detection mechanism investigation revealed that the electron deficient group -CN and the hydroxyl group was oxidized into aldehyde or carbonyl groups at the presence of ClO⁻, resulting ultraviolet-visible absorption of the probe blue shifted and turned-off fluorescence. Furthermore, XA-CN was successfully used for the detection of ClO⁻ in tap water samples.     

Zinc(II)‐selective ratiometric fluorescent probe based on perylene bisimide derivative

A fluorescent probe of N,N′‐biscyclohexyl‐1,7‐di(3‐pyridoxy)‐perylene‐3,4:9,10‐tetracarboxylic acid diimide has been synthesized, and exhibited excellent selectivity and sensitivity for Zn²⁺ over other competing biological cations. The Zn²⁺‐selective fluorescence blue‐shift and enhancing property in conjunction with a visible colorimetric change from orange to green could be observed. With favorable photophysical properties in the visible region, the perylene bisimide derivatives remarkably improved the performance of the probe. Copyright © 2010 John Wiley & Sons, Ltd.     

Synthesis and activity of a coumarin‐based fluorescent probe for hydroxyl radical detection

As a type of reactive oxygen species (ROS), hydroxyl radical (·OH) is closely associated with many kinds of diseases. The present study aimed to develo p a novel OH fluorescent probe based on coumarin, a new compound that has not been previously reported. This probe exhibited good linear range and selectivity for ·OHl, and is able to avoid interference from some metal ions and other kinds of ROS (H₂O₂, O₂^.‐, ¹O₂, and HClO). Meanwhile, this probe has been used to evaluate the ·OH‐scavenging efficiency of different compounds, such as isopropyl alcohol, cytosine, uracil, Tempo, Glutathione (GSH), and dimethyl sulfoxide (DMSO). Therefore, the present study shows that this probe not only can effectively measure the level of ·OH, but also can assess the ·OH‐scavenging efficiency of different compounds. Furthermore this current study suggested that following further optimization, this probe may be potentially applied in the diagnosis of oxidative stress in human body.     

A carbonothioate‐based highly selective fluorescent probe with a large Stokes shift for detection of Hg2+

Mercury (Hg) is one of the heavy metal pollutants in the environment. Even a very small amount of mercury can cause serious harm to human beings. Herein, we reported a new carbonothioate‐based fluorescent probe for the detection of Hg²⁺ without interference from other metal ions. This probe possessed a very large Stokes shift (192 nm), which could improve the detection sensitivity by minimizing the interferences resulted from self‐absorption or auto‐fluorescence. With the addition of Hg²⁺ to the probe solution, considerable fluorescence enhancement was observed. Additionally, the Hg²⁺ concentration of 0–16 μM and fluorescence intensity showed a good linear relationship (y = 22106× + 53108, R² = 0.9955). Finally, the proposed probe was used to detect Hg²⁺ in real water samples, and its result was satisfactory. Therefore, our proposed probe would provide a promising method for the determination of Hg²⁺ in the environment.     

A fast‐responsive fluorescent probe for sulfite and its bioimaging

A turn‐on fluorescent probe Coumarin‐SO2 based on a nucleophilic addition reaction was developed for the rapid detection of SO₃^2– in aqueous media. The probe Coumarin‐SO2 displays excellent water solubility, fast response, highly sensitivity and highly selectivity over other biological related species. More importantly, living cell imaging experiments indicate the feasibility of using the probe for the detection of SO₃^2– in biological systems. Copyright © 2015 John Wiley & Sons, Ltd.     

Application of a luminous intensity variation fluorescent probe for the detection of ferric ions

A luminous intensity variation fluorescent probe (Probe 1) for the detection of ferric ion was developed. The quantitative range of Fe³⁺ content detected was 0–600 μM with the limit of detection at 0.76 μM. Furthermore, after 20 min of Fe³⁺ addition, the intensity of the luminescence of Probe 1 solution gradually decreased with increase in Fe³⁺ concentration. In addition, the B and G values of these images showed a linear relationship with Fe³⁺ concentration (0–500 μM). Probe 1 was successfully used for the rapid determination of Fe³⁺ concentration in real samples. This study demonstrates that Probe 1 is an excellent tool for the rapid determination of Fe³⁺ content in real samples using a smart phone without professional equipment.     

A simple boronic acid-based fluorescent probe for selective detection of hydrogen peroxide in solutions and living cells

An approach of high sensitivity and selectivity for hydrogen peroxide (H₂O₂) detection is highly demanded due to its important roles in regulating diverse biological process. In this work, we introduced an easily synthesized fluorescent “turn off” probe, BNBD. It is designed based on the core structure of 4-chloro-7-nitrobenzofurazan as a fluorophore and incorporated with a specific H₂O₂-reactive group, aryl boronate, for sensitive and selective detection of H₂O₂. We demonstrated its selectivity by incubating the probe with other types of ROS, and measured the limit of detection of BNBD as 1.8 nM. BNBD is also conducive to H₂O₂ detection at physiological conditions. We thus applied it to detect both exogenous and endogenous changes of H₂O₂ in living cells by confocal microscopy, supporting its future applications to selectively monitor H₂O₂ levels and identify H₂O₂-related physiological or pathological responses from live cells or tissues in the near future.     

A magnetic molecular imprinting-based fluorescence probe for sensitive and selective detection of 2,4-D herbicide

A new magnetic molecular imprinting-based turn-on fluorescence probe (Fe₃O₄NPs@SiO₂@NBD@MIPs) has been synthesized via a facile sol–gel polymerization for the detection of 2,4-dichlorophenoxyacetic acid (2,4-D). Based on the photoinduced electron transfer (PET) of nitrobenzoxadiazole (NBD), 2,4-D can be recognized by enhancement of NBD fluorescence. With the presence of Fe₃O₄ in the core of the probe, this sensor can also be reused many times using magnetic aggregation methods. After the addition of various concentrations of 2,4-D, the fluorescence peak at 530 nm (excitation of 468 nm) increased linearly ranging from 0.1 to 3 μM with a detection limit of 0.023 μM. This sensing system is believed to be available for detecting 2,4-D in real samples, with high recovery rates ranging from 94% to 108% for three spike levels of 2,4-D with precisions below 5%.     

A simple rhodamine hydrazide‐based turn‐on fluorescent probe for HOCl detection

Hypochlorous acid (HOCl) plays a crucial role in daily life and mediates a variety of physiological processes, however, abnormal levels of HOCl have been associated with numerous human diseases. It is therefore of significant interest to establish a simple, selective, rapid and sensitive fluorogenic method for the detection of HOCl in environmental and biological samples. A hydrazide‐containing fluorescent probe based on a rhodamine scaffold was facilely developed that could selectively detect HOCl over other biologically relevant reactive oxygen species, reactive nitrogen species and most common metal ions in vitro. Via an irreversible oxidation–hydrolysis mechanism, and upon HOCl‐triggered opening of the intramolecular spirocyclic ring during detection, the rhodamine hydrazide‐based probe exhibited large fluorescence enhancement in the emission spectra with a fast response, low detection limit and comparatively wide pH detection range in aqueous media. The probe was further successfully applied to monitoring trace HOCl in tap water and imaging both exogenous and endogenous HOCl within living cells. It is anticipated that this simple and useful probe might be an efficient tool with which to facilitate more HOCl‐related chemical and biological research. Copyright © 2015 John Wiley & Sons, Ltd.     

A novel highly specific colorimetric fluorescent probe for the detection of nitrite in aqueous solution

Developing an effective method for the detection of nitrite (NO₂⁻) ions in the natural environment especially in environmental waters and soils is very necessary, since they will cause serious damage to human health once excess NO₂⁻ ions enters the human body. Therefore, a new colorimetric fluorescent probe NB-NO₂⁻ for determining NO₂⁻ ions was designed, which possesses good water-solubility and satisfactory selectivity over other common ions for NO₂⁻ ions. The addition of NO₂⁻ ions changed the color of solution from blue to colorless seen by the naked-eye. Furthermore, through test and calculation, the detection limit of the probe NB-NO₂⁻ is 129 nM. Based on the earlier excellent characteristics, the probe NB-NO₂⁻ was successfully used for monitoring NO₂⁻ ions in environmental waters and soils.