CN114249760B - Synthesis and application of fluorescent probe capable of simultaneously distinguishing hypochlorous acid and hydrogen peroxide through three channels - Google Patents
Synthesis and application of fluorescent probe capable of simultaneously distinguishing hypochlorous acid and hydrogen peroxide through three channels Download PDFInfo
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Abstract
The invention discloses a kind ofDetection of hypochlorous acid (HOCl) and hydrogen peroxide (H) is simultaneously distinguished by three different fluorescence emission signals of green, red and yellow 2 O 2 ) The chemical structural formula of the fluorescent probe is as follows:
the fluorescent probe can distinguish HOCl and H under the same detection condition 2 O 2 And both coexist. After the probe reacts with HOCl, the probe emits green light of 504nm at an excitation wavelength of 350nm, and H 2 O 2 After the reaction, 640nm red light is emitted under the excitation wavelength of 430nm, and the red light is reacted with the two (HOCl and H 2 O 2 ) And then emits 550nm yellow light at 440nm excitation wavelength. The probe can detect HOCl and H sequentially through three channels simultaneously 2 O 2 HOCl and H under coexistence conditions 2 O 2 The method has the advantages of high sensitivity, good selectivity, large Stokes shift and the like, and has great application prospect in the technical fields of analytical chemistry, life science, environmental science and the like.
Description
Technical Field
The invention belongs to the technical field of analytical chemistry, and particularly relates to synthesis of a fluorescent probe for detecting hypochlorous acid and hydrogen peroxide, and application of the probe in quantitative analysis of the hypochlorous acid and the hydrogen peroxide in the environment and simultaneous differentiation and imaging of the hypochlorous acid and the hydrogen peroxide in biological systems such as cells, tissues, living bodies and the like.
Background
Reactive oxygen species (Reactive oxygen species, ROS) are essential messenger molecules in a variety of physiological processes (j.amer.chem.soc., 2017,139,6911-6918), including aging, signal transduction, cellular redox homeostasis, and protection against pathogen invasion, among others (spectrochim.acta.a mol.biomol.spectrosc.,2021,246,118927). Hydrogen peroxide (H) 2 O 2 ) And hypochlorous acid (HClO) are two important reactive oxygen species that play an important role in many physiological and pathological processes. There is evidence that excess HClO is associated with various human diseases such as cardiovascular disease, neurodegeneration, arthritis and cancer (anal. Chem.,2017,89,10384-10390); in addition, H produced by intracellular abnormalities 2 O 2 Is involved in various pathological processes such as diabetes, cancer, cardiovascular diseases, neurodegenerative diseases, etc. (anal. Chem.,2016,88,8019-8025). Since a change in the amount of one of the two active oxygen species may cause a related change in the other active oxygen species, many diseases occur in close association with their changes in the amount. Thus, efficient detection methods/techniques have been developed for the simultaneous differential detection of HOCl and H 2 O 2 The understanding of the biological function of these two reactive oxygen species is of great importance. Fluorescence based on small molecule fluorescent probesThe optical imaging technology has become an effective method for visualizing the spatial-temporal distribution of biomolecules in biological systems due to the characteristics of real-time, sensitivity, non-invasiveness and the like (Anal. Chem.,2016,88,8019-8025). Although small molecule active oxygen hypochlorous acid (HOCl) and hydrogen peroxide (H) 2 O 2 ) Has similar chemical properties, but single/double fluorescent channel fluorescent probes have also been developed for detecting HOCl or H 2 O 2 (e.g., J.am. Chem. Soc.,2017,139,6911-6918, chem. Sci.,2018,9,8207-8212, anal. Chem.,2020,92,3262-3269, chem. Commun.,2018,54,9238-9241, etc.). Only very few fluorescent probes can detect HOCl and H simultaneously 2 O 2 The two active oxygen types do not realize three channels to distinguish HOCl and H at the same time 2 O 2 And HOCl and H under the coexistence condition 2 O 2 。
Disclosure of Invention
In view of the above, the present invention aims to overcome the shortcomings of some prior arts, and to provide a fluorescent molecular probe for simultaneously distinguishing and detecting hypochlorous acid and hydrogen peroxide and coexistence thereof by using three-channel fluorescent signals, and to provide some analysis and detection methods and ideas for analysis and detection fields, etc. by using different fluorescent signals to distinguish hypochlorous acid and hydrogen peroxide in biological systems such as imaging cells.
The invention also aims to provide a synthesis and application method of the fluorescent molecular probe for detecting multiple active oxygen, which is simple in preparation method.
The invention adopts a specific technical scheme that three channels simultaneously distinguish synthesis and application of a fluorescent probe of hypochlorous acid and hydrogen peroxide, and the chemical structural formula of the probe is as follows:
the fluorescent probe for simultaneously distinguishing hypochlorous acid and hydrogen peroxide is characterized in that the preparation method of the fluorescent molecular probe comprises the following steps:
step 1 Synthesis of 11-ethyl-3- (pyridin-4-yl) pyran [2,3-b ] phenothiazin-2 (11H) -one
A. Adding proper amount of 10-ethyl-2-hydroxy-10H-phenothiazine-3-formaldehyde and 4-pyridine ethyl acetate into absolute ethyl alcohol, stirring for 8-12 hours at 95 ℃ to obtain red solution,
B. after the reaction is cooled to room temperature, filtering to obtain red solid 11-ethyl-3- (pyridine-4-yl) pyran [2,3-b ] phenothiazin-2 (11H) -ketone;
a. Under the protection of nitrogen, adding 11-ethyl-3- (pyridine-4-yl) pyran [2,3-b ] phenothiazine-2 (11H) -ketone and 4-bromomethyl phenylboronic acid pinacol ester into anhydrous acetonitrile, refluxing and stirring for 12 hours at 100 ℃ to obtain a reddish brown solution,
b. after the reaction cooled to room temperature, it was filtered to give 4- (11-ethyl-2-oxo-2, 11-dihydropyrano [2,3-b ] phenothiazin-3-yl) -1- (4, 5-tetramethyl-1, 3, 2-dioxaboro-2-yl) benzyl) pyridine-1-ammonium bromide as a reddish brown solid.
The fluorescent molecular probe provided by the invention can be used for simultaneously distinguishing and detecting hypochlorous acid and hydrogen peroxide, and the use method comprises the following steps: unless otherwise specified, probe molecules are typically dissolved for analytical detection at room temperature in an environment of 5:5 volume ratio of organic phase to aqueous phase, the organic phase being dimethyl sulfoxide (DMSO), and the aqueous phase being Phosphate Buffered Saline (PBS) at ph=7.4 and an aqueous solution of the analyte.
The fluorescent molecular probe provided by the invention is characterized in that hypochlorous acid and hydrogen peroxide are distinguished at the same time, and the specific characteristics are as follows: the molecular fluorescent probe is dissolved by dimethyl sulfoxide (DMSO), the probe molecules are dissolved in organic phase and aqueous phase (5:5, v/v) solutions, the probe emits green light of 504nm at an excitation wavelength of 350nm after reacting with hypochlorous acid, emits red light of 640nm at an excitation wavelength of 430nm after reacting with hydrogen peroxide, and emits yellow light of 550nm at an excitation wavelength of 440nm after reacting with both. Thus specific excitation and fluorescence emission signals are used to detect specific analytes, and a third fluorescent channel may be used to achieve sequential and co-existence detection of both. The fluorescent molecular probe can realize the simultaneous differential detection of hypochlorous acid and peroxidation under the same detection conditionHydrogen has no obvious response to other active oxygen, active sulfur, common amino acid, metal ion, active nitrogen and the like. Probe detection of HOCl and H 2 O 2 The detection limit of (2) is as low as 51.11nM and 39.45nM, respectively. Therefore, the fluorescent molecular probe disclosed by the invention can realize three channels to distinguish hypochlorous acid and hydrogen peroxide simultaneously.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of a fluorescent probe of the present invention.
FIG. 2 is a fluorescence spectrum of the fluorescent probe for detecting hypochlorous acid and hydrogen peroxide according to the present invention.
FIG. 3 shows the fluorescence probe of the present invention simultaneously imaging hypochlorous acid (HOCl) and hydrogen peroxide (H) endogenous to cells in RAW 264.7 (macrophage) cells by green, red and yellow fluorescence 2 O 2 ) Fluorescence imaging.
Detailed Description
The invention is further described below with reference to the accompanying drawings.
The synthetic route of the fluorescent molecular probe is shown as the following formula:
EXAMPLE 1 Synthesis of 11-Ethyl-3- (pyridin-4-yl) pyran [2,3-b ] phenothiazin-2 (11H) -one I1.0 g (3.69 mmol) of 10-ethyl-2-hydroxy-10H-phenothiazine-3-carbaldehyde and 608.81mg (3.69 mmol) of ethyl 4-pyridineacetate were added to 10mL of absolute ethanol and stirred at 95℃for 8-12 hours to give a red solution, II. After the reaction was cooled to room temperature, filtration afforded 11-ethyl-3- (pyridin-4-yl) pyran [2,3-b ] phenothiazin-2 (11H-one) as a red solid 1.0g in 73.0% yield.
EXAMPLE 2 Synthesis of fluorescent Probe 4- (11-Ethyl-2-oxo-2, 11-dihydropyrano [2,3-b ] phenothiazin-3-yl) -1- (4, 5-tetramethyl-1, 3, 2-dioxaboro-2-yl) benzyl) pyridine-1-ammonium bromide A. 1.0g (2.68 mmol) of 11-Ethyl-3- (pyridin-4-yl) pyran [2,3-b ] phenothiazin-2 (11H) -one and 797.4mg (2.68 mmol) of 4-bromomethylbenzobutyrate were added to 15mL of anhydrous acetonitrile under nitrogen protection, reflux stirring at 100deg.C for 12 hr to give a reddish brown solution, B. after cooling to room temperature, filtering to give 1.5g of 4- (11-ethyl-2-oxo-2, 11-dihydropyrano [2,3-b ] phenothiazin-3-yl) -1- (4, 5-tetramethyl-1, 3, 2-dioxaboro-2-yl) benzyl) pyridine-1-ammonium bromide as a reddish brown solid in 83.3% yield.
Example 3. Application of fluorescent molecular probes in vitro Environment to differentiate detection of hypochlorous acid and hydrogen peroxide the spectroscopic properties of fluorescent molecular probes according to the invention were tested for hypochlorous acid and hydrogen peroxide: the probe was dissolved in dimethyl sulfoxide (DMSO) to prepare a probe solution having a concentration of 1mM, and hypochlorous acid and an aqueous hydrogen peroxide solution having a concentration of 1mM were prepared, respectively. The specific test mode is as follows: mu.L of 1mM probe solution, 980. Mu.L of analytically pure DMSO and the required amount of PBS buffer in water were taken, the required amount of hypochlorous acid/hydrogen peroxide in water in 2mL sample tubes, and all tests maintained a volume ratio of organic phase to aqueous phase of 5:5 (total volume of each test sample was 2 mL). For example, when the probe is required to test the fluorescence intensity after reaction with hypochlorous acid at a hypochlorous acid concentration of 20. Mu.M, the sample is prepared by: 20. Mu.L of 1mM probe solution, 980. Mu.L of analytically pure DMSO, 960. Mu.L of PBS buffer solution, and 40. Mu.L of 1mM hypochlorous acid aqueous solution are taken in a 2mL sample tube, and after shaking for 15 minutes at room temperature, the fluorescence emission intensity can be measured with an excitation wavelength of 350nm, and other test operations are similar to the above steps. The detection limits of the probe for hypochlorous acid and hydrogen peroxide were as low as 51.11nM and 39.45nM, respectively. Therefore, the fluorescent molecular probe disclosed by the invention can realize high-sensitivity distinguishing detection of the fluorescent molecular probe and the fluorescent molecular probe.
EXAMPLE 4 three-channel fluorescence imaging analysis of endogenous hypochlorous acid and Hydrogen peroxide in RAW 264.7 (macrophage) cells RAW 264.7 cells were passaged into confocal dish cell culture medium, after culturing for 24 hours under standard growth conditions, appropriate amount of probe (5. Mu.M) was added to continue culturing under standard growth conditions for 30 minutes, then photographed under confocal fluorescence microscope, and fluorescence imaging of hypochlorous acid and hydrogen peroxide endogenous to RAW 264.7 cells was performed with green, red, yellow fluorescent channels, respectively, as can be seen from FIG. 3, the fluorescent probe of the present invention was capable of emitting green, red, and yellow in cellsColor fluorescence, which shows that the probe can detect hypochlorous acid and hydrogen peroxide in cells and detect the hypochlorous acid and hydrogen peroxide together, thereby successfully realizing endogenous HOCl and H in cells 2 O 2 Three-channel fluorescence imaging analysis. The fluorescent probe for simultaneously distinguishing hypochlorous acid and hydrogen peroxide provided by the invention realizes that different chemical reactions are generated by utilizing the probe, hypochlorous acid and hydrogen peroxide under the same detection condition based on the same probe, and different fluorescent substances are generated, so that fluorescence of three colors of green, red and yellow is emitted under a specific excitation wavelength, the aim of simultaneously distinguishing and detecting the hypochlorous acid and the hydrogen peroxide is fulfilled, and endogenous hypochlorous acid and hydrogen peroxide in three-channel simultaneous fluorescence imaging cells are successfully realized. It is hoped to provide some ideas for the development of active oxygen fluorescent probes in future. While the present invention has been described in detail through the foregoing description of the preferred embodiment, it should be understood that the foregoing description is not to be considered as limiting the invention. Many modifications and substitutions of the present invention will become apparent to those of ordinary skill in the art upon reading the foregoing. Thus, fluorescent probes having the features described herein that distinguish hypochlorous acid from hydrogen peroxide at the same time fall within the scope of protection of this patent.
Claims (3)
1. The three-channel fluorescent probe for simultaneously distinguishing hypochlorous acid and hydrogen peroxide is characterized in that the chemical structural formula of the fluorescent probe is shown as follows:
2. the synthesis of a fluorescent probe according to claim 1, wherein the preparation method of the fluorescent probe comprises the following steps:
step 1, synthesizing 11-ethyl-3- (pyridin-4-yl) pyran [2,3-b ] phenothiazin-2 (11H) -one;
A. adding proper amount of 10-ethyl-2-hydroxy-10H-phenothiazine-3-formaldehyde and 4-pyridine ethyl acetate into absolute ethyl alcohol, stirring for 8-12 hours at 95 ℃ to obtain red solution,
B. after the reaction is cooled to room temperature, filtering to obtain red solid 11-ethyl-3- (pyridine-4-yl) pyran [2,3-b ] phenothiazin-2 (11H) -ketone;
step 2, synthesizing fluorescent probe 4- (11-ethyl-2-oxo-2, 11-dihydropyrano [2,3-b ] phenothiazin-3-yl) -1- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzyl) pyridine-1-ammonium bromide;
a. under the protection of nitrogen, adding 11-ethyl-3- (pyridine-4-yl) pyran [2,3-b ] phenothiazine-2 (11H) -ketone and 4-bromomethyl phenylboronic acid pinacol ester into anhydrous acetonitrile, refluxing and stirring for 12 hours at 100 ℃ to obtain a reddish brown solution,
b. after the reaction cooled to room temperature, it was filtered to give 4- (11-ethyl-2-oxo-2, 11-dihydropyrano [2,3-b ] phenothiazin-3-yl) -1- (4, 5-tetramethyl-1, 3, 2-dioxaboro-2-yl) benzyl) pyridine-1-ammonium bromide as a reddish brown solid.
3. The use of a fluorescent probe according to claim 1 for the preparation of a device, wherein the device prepared is capable of quantitatively analyzing HOCl and H in an environment 2 O 2 And simultaneously differentiating imaging HOCl and H in cells, tissues and living bodies 2 O 2 。
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