CN114763353A - Imidazopyridine mother nucleus-based fluorescence detection reagent and detection technology for signal molecule H2S by using same - Google Patents
Imidazopyridine mother nucleus-based fluorescence detection reagent and detection technology for signal molecule H2S by using same Download PDFInfo
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- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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Abstract
The invention discloses a fluorescence detection reagent based on an imidazopyridine parent nucleus and a signal molecule H thereof2The detection technology of S, the fluorescent reagent is a near-infrared fluorescent probe, and the chemical structural formula is as follows:
Description
Technical Field
The invention belongs to the technical field of analytical chemistry, relates to a preparation method of an imidazopyridine-based parent nucleus fluorescence detection reagent, and particularly relates to an application of the fluorescence detection reagent in detection of signal molecule hydrogen sulfide in an environmental system (including aqueous solution) and in a living body.
Background
Hydrogen Sulfide (Hydrogen Sulfide, H)2S) is a gas with a distinctive odor, in addition to which it is a third novel endogenous gas signaling molecule found after nitric oxide and carbon monoxide. Endogenous H2S can be produced by catalyzing 5-pyridoxal phosphate-dependent enzymes (including cystathionine-beta-synthase (CBS), cystathionine-gamma-lyase (CSE), cysteine transferase) with L-cysteineSheng plays an important role in various physiological and pathological processes in vivo. E.g. endogenous H2S can participate in hemoglobin change, can also be used as physiological vasodilatation factors and blood pressure regulating factors of a cardiovascular system, can dilate vascular smooth muscle, inhibit vascular remodeling and negative muscle force acting on the heart, improve myocardial oxidative stress injury and the like, and thus has the effect of protecting the heart. Generally, H in blood2S concentration in the range of 10-100. mu.M, high concentration of H2S is liable to cause damage to tissues such as the human nervous system and the brain, and shows symptoms of central nervous system and asphyxia, which has been considered by scholars as H2S is closely related to important diseases such as Alzheimer' S disease, cardiovascular diseases, cancer and the like. Thus, in vivo H2The high selectivity and high sensitivity detection of S is of great significance to biological research and clinical diagnosis.
To date, many chemical methods have been developed, such as colorimetry, gas chromatography, electrochemical analysis, metal-induced sulfide precipitation, etc., but these methods can only be used for H due to the need to destroy biological samples2And (4) detecting S in vitro. In contrast, fluorescence imaging based on fluorescent probes is considered to be one of the most effective methods for monitoring biological species in living cells due to its high sensitivity, good selectivity, low cost, especially non-destructive nature and advantages of real-time in situ detection. Although it has been available for intracellular H2Fluorescent molecular probes for S detection are developed, but most of the maximum emission wavelengths of the fluorescent molecular probes are located in the ultraviolet visible region (400-600nm), so that the tissue penetration capability is weak, the tissue injury is strong, and the fluorescent molecular probes are easily interfered by background fluorescence in organisms, so that the sensitivity and the accuracy of the probes are influenced.
Disclosure of Invention
In view of the problems of the prior art, the first object of the present invention is to provide a method for detecting H in water solution and living body with high sensitivity and specificity2S, detecting a near-infrared fluorescence detection reagent;
the second purpose of the invention is to provide a fluorescent probe synthesis method which has simple synthesis route, low cost and simple operation and is suitable for large-scale popularization.
The technical scheme adopted for solving the problems is that the fluorescent detection reagent based on the imidazopyridine parent nucleus has the following structural formula:
the synthetic route is as follows:
the specific synthesis method comprises the following steps:
1) dissolving 2-benzoylpyridine, salicylaldehyde and ammonium acetate in acetic acid, and reacting at 90 deg.CoHeating and refluxing under C, and monitoring by TLC until the reaction is complete. After the reaction is finished, cooling the reaction system to room temperature, pouring the reaction system into ice water, collecting a solid by suction filtration, washing the solid with water, and recrystallizing acetonitrile to obtain a compound 1;
2) dissolving compound 1 and hexamethyl-hydroxylamine in trifluoroacetic acid, and reacting the mixture in a reaction system of 90oC heating reflux, TLC monitoring till the reaction is complete. After the reaction is finished, cooling the reaction system to room temperature, pouring the reaction system into ice water, adjusting the pH value to be nearly neutral by using a NaOH solution, separating out a large amount of precipitates, carrying out suction filtration, collecting and washing a filter cake, carrying out vacuum drying, and carrying out column chromatography purification to obtain a compound 2;
3) adding compound 2, 2-methyl pyridine salt into 10mL ethanol, adding piperidine after fully dissolving, and putting the reaction system into 90 DEG CoC heating reflux, TLC monitoring till the reaction is complete. After the reaction is finished, cooling the reaction system to room temperature, concentrating under reduced pressure, and purifying by column chromatography to obtain a compound 3;
4) dissolving the compound 3 in a 25mL round-bottom flask filled with anhydrous dichloromethane under the protection of nitrogen and ice bath, dropwise adding triethylamine into the reaction system, and slowly dropwise adding a dichloromethane solution dissolved with 2, 4-dinitrochlorobenzene and 0oStirring under C, and monitoring the reaction by TLCThe reaction is completed. Respectively using water and saturated NaHCO3Extracting the solution with saturated saline solution, combining organic layers, drying with anhydrous magnesium sulfate, concentrating, and purifying by column chromatography to obtain the target fluorescent probe.
The fluorescent probe test method of the present invention is as follows, the probe molecules are dissolved in PBS buffer solution with pH7.4, and the test is carried out at room temperature. The hydrogen sulfide can be quantitatively detected, and the specific implementation method is described in detail in the implementation examples.
The response mechanism of the fluorescent probe of the present invention is as follows:
since the 2, 4-dinitro-phenyl ether group prevents the excited-state intramolecular proton transfer Effect (ESIPT) of the probe, the probe only generates enol emission when H is added2After S, due to H2S can selectively cut 2, 4-dinitro benzene ether bond in the molecular probe to release hydroxyl, and the ESIPT function of the probe is recovered, so that the probe recovers ketone emission, and the fluorescence of the system at 646 nm is obviously enhanced. The response process of the probe molecule is as follows:
compared with the prior art, the technical scheme of the invention has the beneficial technical effects that:
the imidazopyridine-based parent nucleus fluorescence detection reagent has the advantages of simple synthetic route, simple operation, low cost, high sensitivity, strong specificity, strong tissue penetrating power, small tissue damage, small interference of background fluorescence and the like, and the maximum emission wavelength is in a near infrared region, and has practical application value in a plurality of systems in the fields of environmental science, life science and the like.
Drawings
FIG. 1 is a fluorescence emission spectrogram of fluorescence intensity of the fluorescence detection reagent varying with sodium sulfide concentration in the practice of the present invention;
FIG. 2 is a graph showing the linear relationship between the fluorescence intensity of the fluorescence detection agent and the concentration of sodium sulfide in the practice of the present invention;
FIG. 3 is a graph showing the selectivity of the fluorescence detection reagent for sodium sulfide in the practice of the present invention;
FIG. 4 is a confocal image of fluorescence of a fluorescence detection reagent in HeLa cells in the practice of the present invention.
Detailed Description
The following embodiments are intended to further illustrate the present invention and are not intended to limit the present invention.
Example 1
Synthesis of Compound 1
2-benzoylpyridine (1832.06 mg, 10mmol), salicylaldehyde (1831.82 mg, 15 mmol) and ammonium acetate (4239.57 mg, 55 mmol) were dissolved in 50mL acetic acid, and the reaction was taken up in 90 mL acetic acidoHeating and refluxing under C, and monitoring by TLC until the reaction is complete. After the reaction is finished, the reaction system is cooled to room temperature, poured into 500mL of ice water, a large amount of precipitate is generated, solid is collected by suction filtration, and after washing with water, acetonitrile is recrystallized to obtain 1924.12 mg of a product, wherein the yield is 67.2%.
Synthesis of Compound 2
Compound 1 (1869.72 mg, 6.5mmol) and hexamethyl-hydroxylamine (3644.68 mg, 26mmol) were dissolved in 25mL of trifluoroacetic acid, and the reaction was taken up in 90 mL of wateroC heating reflux, TLC monitoring till the reaction is complete. After the reaction is finished, cooling the reaction system to room temperature, pouring the reaction system into 500mL of ice water, adjusting the pH value to about 6 by using a 1N NaOH solution, separating out a large amount of precipitates, carrying out suction filtration, collecting and washing a filter cake, carrying out vacuum drying, and carrying out column chromatography purification to obtain 766.20 mg of a product, wherein the yield is 37.5%.1H NMR (400 MHz, CDCl3) δ 9.98 (s, 1H), 8.55 (d, J=7.3 Hz, 1H), 7.86 (dd, J=8.0, 6.0 Hz, 3H), 7.76 (dd, J=7.9, 1.0 Hz, 1H), 7.45 (t, J=7.8 Hz, 2H), 7.36-7.30 (m, 2H), 7.19 (d, J=7.6 Hz, 1H), 7.02 (dd, J=11.0, 4.2 Hz, 1H), 6.87 (dd, J=9.2, 6.4 Hz, 1H), 6.69 (t, J=6.5 Hz, 1H)。
Synthesis of Compound 3
Compound 2 (628.68 mg, 2mmol) and 2-methylpyridine salt (702 mg, 2.75mmol) were added to 10mL of ethanol, and the mixture was dissolved sufficiently and thenAdding 1mmol of piperidine, and reacting at 90 deg.CoC heating reflux, TLC monitoring till the reaction is complete. After the reaction is finished, the reaction system is cooled to room temperature, and is subjected to column chromatography purification after being concentrated under reduced pressure, so that 864.04 mg of a product is obtained, and the yield is 81.3%.1H-NMR (400 MHz, DMSO-d6, TMS): δ 8.93 (d, J=8.6 Hz, 1H), 8.60 (d, J=7.3 Hz, 1H), 8.10 (t, J=8.2 Hz, 1H), 8.04 (d, J=7.4 Hz, 1H), 7.78 (s, 1H), 7.66 (t, J=8.2 Hz, 1H), 7.52-7.50 (m, 3H) , 7.47 (t, J=7.8 Hz, 2H), 7.41(t, J=8.4 Hz, 1H), 7.29 (d, J=7.6 Hz, 1H), 7.06 (dd, J=11.0, 4.2 Hz, 1H), 7.02 (d, J=7.6 Hz, 1H), 6.99 (d, J=8.2 Hz, 1H), 6.95 (d, J=16.0 Hz, 1H), 6.87 (dd, J=9.2, 6.4 Hz, 1H), 5.35(s, 1H), 4.39 (s, 3H)。
Synthesis of target molecular probes
Under the protection of nitrogen and ice bath, dissolving the compound 3 (531.39 mg, 1 mmol) in a 25mL round-bottom flask containing 10mL of anhydrous dichloromethane, dropwise adding triethylamine into the reaction system, and slowly dropwise adding a dichloromethane solution containing 1mmol of 2, 4-dinitrochlorobenzene, 0oStirring under C, and monitoring the reaction by TLC until the reaction is complete. Respectively using water and saturated NaHCO3Extracting the solution with saturated saline solution, combining organic layers, drying with anhydrous magnesium sulfate, concentrating, and purifying by column chromatography to obtain 500.79 mg of target fluorescent probe with a yield of 71.8%.1H-NMR (400 MHz, DMSO-d6, TMS): δ8.94 (d, J=8.2 Hz, 1H), 8.88 (s, 1H), 8.62-8.60 (m, 2H), 8.12 (t, J=8.4 Hz, 1H), 8.06 (d, J=7.6 Hz, 1H), 7.91 (s, 1H), 7.66-7.64 (m, 2H), 7.51 (t, J=7.8 Hz, 2H) , 7.46 (t, J=7.8 Hz, 2H), 7.40(t, J=8.4 Hz, 1H), 7.27 (d, J=8.4 Hz, 1H), 7.15 (d, J=8.5 Hz, 1H), 7.10 (d, J=8.0 Hz, 1H), 7.04 (dd, J=11.0, 4.2 Hz, 1H), 7.02 (d, J=8.2 Hz, 1H), 6.95 (d, J=16.0 Hz, 1H), 6.88 (dd, J=9.2, 6.4 Hz, 1H), 4.40 (s, 3H). HR-MS (ESI, positive), m/z: calculated [M-I]+:570.1774, found [M-I]+: 570.1979。
Example 2
Fluorescence spectrum of fluorescence detection reagent at different sodium sulfide concentrations
This patent uses sodium sulfide in an aqueous solution to supply hydrogen sulfide. The fluorescent probe was dissolved in PBS buffer (10 mM, pH = 7.4) to prepare a fluorescent detection reagent. A sodium sulfide solution was added thereto so that the concentration of the probe in the final detection system was 10. mu.M, and the concentrations of sodium sulfide were 0. mu.M, 1. mu.M, 2. mu.M, 4. mu.M, 7. mu.M, 10. mu.M, 15. mu.M, 20. mu.M, 25. mu.M, and 30. mu.M, respectively. After incubation at room temperature for 20 min, the fluorescence spectra of the different systems were tested in 10mm cuvettes, respectively. The fluorescence spectrum is shown in FIG. 1. The results show that the fluorescence emission intensity of the system at 646 nm is gradually enhanced with the increase of the concentration of the added sodium sulfide. Meanwhile, a linear fitting graph (figure 2) for detecting hydrogen sulfide is prepared, and the result shows that when the concentration of sodium sulfide is in a range interval of 0-7 mu M, the fluorescence intensity at 646 nm and H2The concentration of S has a good linear relation, the regression linear equation is y =17.12937x +9.0072, and the linear correlation coefficient is as follows: 0.99478, and the limit of detection (LOD) was calculated to be 0.054. mu.M (S/N-3), indicating that the fluorescent probe has good sensitivity.
Example 3
Selectivity of fluorescent detection reagent to sodium sulfide
Dissolving the fluorescent probe in PBS buffer solution (10 mM, pH = 7.4) to prepare a fluorescent detection reagent, and adding different solutions of the substance to be detected into the fluorescent detection reagent to ensure that the concentration of the probe in the final detection system is 10 mu M, and the concentration of sodium sulfide is 25 mu M, Hcy, GSH, Val, Tyr, His and H2S、PhSH、Ca2+、OH-After incubation at room temperature for 20 min at a concentration of 100. mu.M, the fluorescence spectra of the different systems were measured in 10mm cuvettes, respectively, and the results are shown in FIG. 3. Found only with H2In response to S, the fluorescence of the fluorescent probe changes significantly, whereas when other test substances are added, the probe changes only slightly or does not change. The fluorescent probe is shown to have good selectivity and can effectively avoid the interference of other active molecules.
Example 4
Imaging application of fluorescence detection reagent in living cells
Hela cells were placed in a culture medium (DMEM medium and 10% fetal bovine serum) under 37% conditionsoC、5 % CO2Was cultured in an incubator for 24 hours. The fluorescent probe (10. mu.M) of the present invention was pipetted by a micro-injector into the culture medium containing Hela cells, and the incubation was continued in the incubator for 30 minutes. 100 μ M sodium sulfide solution was added and incubation was continued for 30 minutes. The cultured cells were washed 3 times with PBS, subjected to fluorescence imaging, and observed for change in fluorescence under a fluorescence microscope, and the results are shown in FIG. 4. Experiments show that the probe molecules entering the cell body react with hydrogen sulfide, so that the fluorescent probe has good imaging effect on the hydrogen sulfide in the cell and can be used for detecting H in the organism2S。
Although the present invention has been described with reference to the specific embodiments shown in the drawings, it is not intended to limit the scope of the present invention, and various modifications or variations can be made by those skilled in the art from the disclosure of the present invention without inventive efforts.
Claims (6)
1. The fluorescence detection reagent based on the imidazopyridine parent nucleus is characterized in that the structural formula of a used fluorescence probe is as follows:
2. the method of claim 1 for preparing a fluorescent probe for detecting signal molecule hydrogen sulfide, comprising the steps of: dissolving 2-benzoylpyridine, salicylaldehyde and ammonium acetate in acetic acid, and reacting at 90 deg.CoHeating and refluxing under C, and monitoring by TLC until the reaction is complete; after the reaction is finished, cooling the reaction system to room temperature, pouring the reaction system into ice water, collecting a solid by suction filtration, washing the solid with water, and recrystallizing acetonitrile to obtain a compound 1; the structural formula of the compound 1 is shown as follows:
3. dissolving compound 1 and hexamethyl-hydroxylamine in trifluoroacetic acid, and reacting the mixture in a reaction system of 90oC, heating and refluxing, and monitoring by TLC until the reaction is complete; after the reaction is finished, cooling the reaction system to room temperature, pouring the reaction system into ice water, adjusting the pH value to be nearly neutral by using a NaOH solution, separating out a large amount of precipitates, carrying out suction filtration, collecting and washing a filter cake, carrying out vacuum drying, and carrying out column chromatography purification to obtain a compound 2;
the structural formula of the compound 2 is shown as follows:
4. adding the compound 2 and 2-methylpyridine salt into 10mL of ethanol, adding piperidine after fully dissolving, and reacting the reaction system at 90 DEGoC, heating and refluxing, and monitoring by TLC until the reaction is complete; after the reaction is finished, cooling the reaction system to room temperature, concentrating under reduced pressure, and purifying by column chromatography to obtain a compound 3; the structural formula of the compound 3 is shown as follows:
5. dissolving the compound 3 in a 25mL round-bottom flask filled with anhydrous dichloromethane under the protection of nitrogen and ice bath, dropwise adding triethylamine into the reaction system, and slowly dropwise adding a dichloromethane solution dissolved with 2, 4-dinitrochlorobenzene and 0 oStirring under C, and monitoring the reaction by TLC until the reaction is complete; respectively using water and saturated NaHCO3Extracting the solution with saturated saline solution, combining organic layers, drying with anhydrous magnesium sulfate, concentrating, and purifying by column chromatography to obtain the target fluorescent probe.
6. The use of the fluorescent detection reagent for detecting hydrogen sulfide as claimed in claim 1, wherein the reagent is used for the fluorescent detection and cell imaging detection of hydrogen sulfide content in environmental and biological samples to be detected.
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| CN116283968A (en) * | 2023-02-20 | 2023-06-23 | 广东省科学院测试分析研究所(中国广州分析测试中心) | Acetamido imidazopyridine compound and preparation method and application thereof |
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