CN113735796A - Design synthesis and property research based on phenothiazine reversible fluorescent probe - Google Patents
Design synthesis and property research based on phenothiazine reversible fluorescent probe Download PDFInfo
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Abstract
The invention relates to the field of fluorescent probes, provides synthesis of a fluorescent probe with good selectivity on GSH, and particularly relates to a reversible fluorescent probe capable of specifically recognizing GSH, which is designed and synthesized by taking phenothiazine as a luminophore and taking Michael reaction acceptor-active double bond as a reaction site. The structural formula is as follows:
Description
Technical Field
The invention relates to the field of fluorescent probes, in particular to a reversible fluorescent probe with good GSH selectivity, which is designed and synthesized by taking phenothiazine as a luminophore and taking Michael reaction acceptor-active double bonds as reaction sites.
Background
Glutathione is a small molecule mercaptan with the largest content in organisms, the content of other thiols in organisms such as cysteine is less than one percent of that of glutathione, and the content of homocysteine is less than one thousandth of that of glutathione. It is widely present in animals and plants, and plays important physiological roles in organisms, such as participating in intracellular redox reactions, intracellular signal transmission, and in vivo metabolism. Simultaneously, the glutathione also plays an important physiological role in a biochemical defense system in a human body, and the main physiological role of the glutathione is to remove free radicals in the human body, be used as an important antioxidant in the human body and protect molecules such as various proteins and enzymes.
In view of the fact that glutathione plays an important physiological role in organisms and the abnormal change of the content of glutathione in organisms is often related to certain diseases, the detection of glutathione attracts attention. There are many methods for detecting bio-thiol, such as electrochemical detection and high performance liquid chromatography, but these methods often have their own limitations, such as large sample size or long detection time. The detection of the fluorescence probe on the biological mercaptan has the advantages of low detection line, no damage, visualization, high speed and the like, and is increasingly viewed in the aspect of biological mercaptan detection.
In recent years, the development of biomolecular thiol fluorescent probes is long, and various fluorescent probes are generated, so that a new method is provided for detecting thiol in organisms. However, the selective detection of biomolecular thiols still faces a great challenge, and the physiological structures of different thiol small molecules are different, so that the selective fluorescent probe has great significance.
Disclosure of Invention
The invention provides synthesis of a fluorescent probe with good selectivity on GSH by taking phenothiazine as a fluorophore. In particular to a reversible fluorescent probe for recognizing GSH, which is designed and synthesized by taking phenothiazine as a luminophore and taking Michael reaction acceptor-active double bond as a reaction site.
The invention provides a fluorescent probe with good selectivity on GSH, wherein the name of the fluorescent probe is (E) -2-cyano-3- (10-ethyl-10H-phenothiazin-3-yl) -N, N-dimethylacrylamide, the name of the fluorescent probe is (E) -2-cyano-3- (10-ethyl-10H-phenothiazin-3-yl) -N, N-dimethylacrylamide, and the structural formula is as follows:
the preparation method of the fluorescent molecular probe comprises the following steps:
The application of the fluorescent probe comprises the following steps of distinguishing and detecting Cys, Hcy and GSH:
after 35 min of probe (10 μ M) in PBS (pH = 7.4) buffer containing 1% DMSO in response to Cys (200 μ M), Hcy (15 μ M) and GSH (5 mM), it can be seen from the UV absorption spectrum that the probe has almost no significant change in Cys and Hcy, but has significant response to GSH, and the peaks at 310 nm and 435 nm are significantly reduced. After the probe reacts with GSH, the fluorescence intensity of the probe is obviously reduced, and the probe has almost no obvious change to Cys and Hcy. The probe is considered to react with GSH, and the mercapto group and the active double bond have Michael addition reaction, thereby influencing the fluorescence of the probe. Cys and Hcy have limited interaction with the probe due to their low concentrations, and have high GSH content, with significant interaction with the probe. Thereby realizing the selection of the biological thiol GSH.
The application of the fluorescent probe, the titration of the probe and the GSH and the detection line measurement are as follows:
fluorescence intensity at 606 nm after reaction of probe (10 μ M) with GSH (1-10 mM) in PBS (pH =7.4, 1% DMSO) was monitored over a GSH concentration range of 0-10 mM. As the concentration of GSH increases, the fluorescence intensity of the emission peak at 606 nm also decreases. We performed tests with GSH at concentrations of 0-10 mM and fitted the probe linearly to the concentration of GSH (0-5 mM) based on the test results and found that at GSH concentrations less than 5mM, the fluorescence intensity is linearly related to the concentration of GSH with the equation of a straight line y = -147.11x + 764.89. When the GSH concentration reached 5mM, the fluorescence intensity remained within a relatively stable range with almost no change in fluorescence intensity, and the lowest detection limit for GSH was calculated to be 1.07. mu.M (0-10 mM for GSH in cells).
Drawings
FIG. 1 scheme for the synthesis of the probe.
FIG. 2 UV absorption and fluorescence emission spectra of probes (10 μ M) in PBS buffer containing 1% DMSO (pH = 7.4) in response to Cys (200 μ M), Hcy (15 μ M) and GSH (5 mM) for 35 min.
FIG. 3 is a graph of fluorescence emission spectra of probes (10. mu.M) in PBS buffer containing 1% DMSO (pH = 7.4) after 35 min response to 0-10 mM GSH, and a graph of fluorescence intensity at 606 nm and linear relationship in the range of 0-5 mM GSH.
Figure 4 graph of probe (10 μ M) versus GSH (5 mM) response in PBS buffer (pH = 7.4) containing 1% DMSO, fluorescence intensity at 606 nm as a function of time.
Figure 5 graph of probe (10 μ M) fluorescence intensity change at 606 nm in PBS buffer pH =4-10 (pH = 7.4) containing 1% DMSO; graph of fluorescence intensity at 606 nm after response 35 min for probe (10 μ M) and GSH (5 mM) in PBS buffer pH =4-10 containing 1% DMSO.
Figure 6 graph of fluorescence intensity at 606 nm of probes (10 μ M) after response to different amino acids and common cations in human in PBS buffer containing 1% DMSO (pH = 7.4).
Figure 7 graph of the change in fluorescence intensity at 606 nm of probe (10 μ M) and GSH (2 mM) in PBS buffer (pH = 7.4) containing 1% DMSO.
Detailed Description
EXAMPLE 1 preparation of fluorescent Probe
The preparation route of the fluorescent probe of the invention is shown in figure 1.
(1) Preparation of Compound a1
Phenothiazine (0.199 g, 1 mmol) was added to a reaction flask (100 mL), and 20 mL of DMSO was added to the reaction flask and dissolved by stirring. Sodium hydride (0.166 g, 1 mmol) was added to the reaction flask and the materials were mixed and stirred under nitrogen for 0.5 h. Measuring bromoethane (0.074 mL, 1 mmol), adding into a reaction bottle, reacting at room temperature under the protection of nitrogen for 24 hours, tracing by a TLC point plate, determining whether the reaction is finished, washing with distilled water after the reaction is finished, extracting with dichloromethane (40 mL, 3 times), drying with anhydrous magnesium sulfate, carrying out vacuum filtration, spinning off the excess solvent, selecting a proper eluent (PE: EA (v: v) = 10: 1), and purifying by column chromatography. Finally, 0.163 g of a white solid was obtained in a yield of 72%. 1H NMR (400 MHz, DMSO). delta.7.19 (t, J = 12.0 Hz, 2H), 7.14 (d, J = 8.0 Hz, 2H), 7.02 (d, J = 8.0 Hz, 2H), 6.93 (t, J = 8.0 Hz, 2H), 3.92 (q, J = 8.0 Hz, 4H), 1.29 (t, J = 8.0 Hz, 3H).
(2) Preparation of intermediate compound a2
DMF (2 mL) was added to a two-necked flask (100 mL), and POCl3 (2 mL) was gradually added dropwise to the flask and refluxed at 50 ℃ under nitrogen for 30 min. Intermediate a1 (0.16 g, 0.7 mmol) was dissolved in 1, 2-dichloroethane (15 mL) and transferred to an isopiestic dropping funnel where it was added slowly to the two-necked flask. Stirring and refluxing for 12 hours at 90 ℃ under the protection of nitrogen, tracing by a TLC point plate, and determining whether the reaction is finished or not until the reaction is finished. Cooled to room temperature and quenched in an ice-water bath by slow addition of distilled water. The pH was adjusted to neutral with 20% NaOH solution, washed with distilled water, extracted with dichloromethane (40 mL, 3 times), dried over anhydrous magnesium sulfate, filtered under reduced pressure, the excess solvent was decanted off, and the appropriate eluent (PE: EA (v: v) = 10: 1) was selected and purified by column chromatography. Finally, 0.13g of a pale yellow solid was obtained in a yield of 75%. 1H NMR (400 MHz, DMSO). delta.9.79 (s, 1H) 7.73(d, J = 8.0 Hz, 1H), 7.58 (s, 1H), 7.23 (t, J = 8.0 Hz, 1H), 7.16 (d, J = 8.0 Hz, 2H), 7.09(d, J = 8.0 Hz, 1H), 7.02 (t, J = 8.0 Hz, 1H), 4.00 (q, J = 8.0 Hz, 4H), 1.32 (t, J = 8.0 Hz, 3H).
(3) Preparation of fluorescent probes
Intermediate a2 (0.127 g, 0.5 mmol) was added to a reaction flask (100 mL), 20 mL of ethanol was measured and added to the flask and stirred to dissolve, 2-cyano-N, N-dimethylacetamide (0.084 g, 1.5 mmol) was added, 52. mu.L of piperidine was added, and the mixture was stirred and refluxed at 80 ℃ under nitrogen for 8 hours and followed by TLC spot plate to determine whether the reaction was complete. After the reaction was completed, the reaction mixture was washed with distilled water, extracted with dichloromethane (40 mL, 3 times), dried over anhydrous magnesium sulfate, suction-filtered under reduced pressure, and the excess solvent was removed by centrifugation, and an appropriate eluent (PE: EA (v: v) = 10: 1) was selected and purified by column chromatography. Finally, 0.078 g of a dark yellow solid is obtained, yield 45%. 1H NMR (400 MHz, CDCl 3): δ 7.77(d, J = 8.0 Hz, 1H), 7.61 (d, J = 8.0 Hz, 1H), 7.16 (t, J = 8.0 Hz, 1H), 7.10 (d, J = 8.0 Hz, 1H), 6.95(t, J = 8.0 Hz, 1H), 6.88 (t, J = 8.0 Hz, 2H), 3.97 (q, J = 8.0 Hz, 4H), 3.21(s, 3H), 3.06(s, 3H), 1.44 (t, J = 8.0 Hz, 3H), 13C NMR (100 MHz, CDCl3) δ 164.45, 150.86, 148.30, 143.12, 130.14, 128.90, 127.54, 127.46, 126.44, 124.39, 123.39, 123.10, 116.61, 115.36, 114.58, 3942, 3942.33.
Example 2 spectroscopic analysis of Probe and thiol response
To explore the response of the probe to different thiols, we performed a spectroscopic analysis of the reaction of the probe with the thiol. As shown in the figure, the spectral responses of the probe (10 [ mu ] M) and Cys (200 [ mu ] M), Hcy (15 [ mu ] M) and GSH (5 mM) are tested, and the probe has almost no obvious change on Cys and Hcy and has obvious response on GSH from the ultraviolet absorption spectrum, and the peaks at the wavelengths of 310 nm and 435 nm have obvious reduction. The same phenomenon can be seen from the fluorescence emission spectrum as shown in FIG. 2(b), and the fluorescence intensity of the probe is significantly reduced after the probe reacts with GSH, while the probe has almost no significant change for Cys and Hcy. The probe is considered to react with GSH, and the mercapto group and the active double bond have Michael addition reaction, thereby influencing the fluorescence of the probe. Cys and Hcy have limited interaction with the probe due to their low concentrations, and have high GSH content, with significant interaction with the probe.
Example 3 titration experiment of Probe with GSH
In order to investigate the response of the probe to GSH with different concentrations of 0-10 mM, we performed a titration experiment, and as can be seen from the fluorescence emission spectrum in fig. 3(a), as the GSH concentration increases, under the GSH condition of 0-5 mM, the fluorescence of the probe itself at 606 nm continuously decreases, which indicates that the probe has a very high sensitivity and can detect GSH with 0-5 mM, and that the fluorescence signal of the GSH with 6-10 mM is not clearly distinguished after the GSH and the probe stabilize, which may be due to the excessive concentration, so the probe cannot clearly distinguish GSH with 6-10 mM.
Example 4 Probe detection line assay
Fluorescence intensity at 606 nm after reaction of the probe (10 μ M) with GSH (1-10 mM) in PBS (pH 7.4, 1% DMSO) was monitored over a GSH concentration range of 0-10 mM. As the concentration of GSH increased, the fluorescence intensity of the emission peak at 606 nm also decreased, as shown in FIG. 3 (b). We performed tests with GSH at a concentration of 0-10 mM and fitted the probe linearly to the concentration of GSH (0-5 mM) according to the test results, and found that the fluorescence intensity at a concentration of GSH less than 5mM is linearly related to the concentration of GSH as shown in FIG. 3(c), and the equation for the straight line is y = -147.11x + 764.89. After the GSH concentration reached 5mM, the fluorescence intensity remained within a relatively stable range, with almost no fluorescence intensity. As shown in the figure, the lowest detection limit of GSH was calculated to be 1.07. mu.M (GSH in cells is 0-10 mM).
EXAMPLE 5 determination of Probe and GSH response time
The response time of probe 1 to GSH was measured, as shown in FIG. 4, using a probe concentration of 10. mu.M, and the fluorescence intensity at 606 nm after the addition of GSH (5 mM) was collected, from which it can be seen that the fluorescence intensity at 606 nm rapidly decreases after the addition of 5mM GSH and stabilizes within 35 min. The response of the probe and the GSH is very quick and is basically complete within 35 min, so the response time of the probe and the GSH is 35 min.
EXAMPLE 6 stability testing of probes
The stability of the probe was then tested and tested for its stability and ability to respond to GSH in PBS buffered solutions of different pH values, and the results are shown. As can be seen from FIG. 5(a), the fluorescence intensity of the probe itself hardly changes in the range of pH =4-10 in the PBS buffer solution, indicating that the probe itself has good pH stability and is not affected by pH to change the fluorescence intensity. Meanwhile, the response ability of the probe to GSH was also tested in the range of pH =4-10, and it can be seen from fig. 5(b) that the probe could not detect GSH well under acidic condition and could detect GSH well under neutral and alkaline condition in the range of pH = 7-10. The pH value under physiological conditions is 7.4, so the probe can be used for detecting GSH under physiological conditions.
EXAMPLE 7 Selective testing of probes
Next, a selectivity test is performed to determine whether the probe has good selectivity for GSH identification according to the test result, which is shown in fig. 6. The ability of the probe to respond to several common amino acids was tested, and it can be seen from the figure that the common amino acids were added to the 10 μ M probe added PBS (pH = 7.4), except that the fluorescence intensity of Hcy (15 μ M) and Cys (200 μ M) at 606 nm was slightly decreased, the fluorescence intensity of other amino acids at 606 nm did not change significantly, indicating that the probe hardly responded to other amino acids. Meanwhile, various cations exist in organisms, and then the response capability of the probe to the cations is tested, and the test result is shown in the figure, although partial cations and the probe respond, the responses of the cations and the probe are weak compared with the response of the probe to the GSH, and the influence of the responses on the amount of addition products in the organisms is negligible, so that the recognition of the probe to the GSH can be judged to have good selectivity.
Example 8 reversibility verification of Probe and GSH reaction
To confirm the reversibility of the reaction of the probe with GSH, a reversible mechanism verification experiment was performed to monitor the change in fluorescence intensity at 606 nm during the reaction, as shown in fig. 7. GSH (2 mM) is selected to react with a probe (10 mu M), the fluorescence intensity at 606 nm gradually decreases, the fluorescence intensity tends to be stable about 35 min, the reaction is indicated to reach an equilibrium state, and H is added into the system after the reaction is stable2O2(5 mM) was allowed to react with GSH, at which time the fluorescence intensity at 606 nm of the probe gradually recovered, which is an experimental phenomenon indicating that the reaction of the probe with GSH is a reversible reaction.
Claims (4)
1. The synthesis and property research based on the phenothiazine reversible fluorescent probe is characterized in that the chemical structural formula of the fluorescent molecular probe is as follows:
。
2. the synthesis of a phenothiazine-based reversible fluorescent probe as claimed in claim 1, wherein the preparation method of the fluorescent molecular probe comprises the following steps: step 1 is the preparation of a compound 10-ethyl-10H-phenothiazine, which is to add phenothiazine into DMSO, add a proper amount of sodium hydride into the system, mix and stir for 0.5 hour, add bromoethane with the same molar ratio as phenothiazine into the system, react for 24 hours at room temperature under the protection of nitrogen, extract and dry after the reaction is finished, remove the solvent, and obtain a target substance through column chromatography; step 2 is the preparation of the compound 10-ethyl-10H-phenothiazine-3-formaldehyde: dissolving a proper amount of 10-ethyl-10H-phenothiazine in 1, 2-dichloroethane, dropwise adding a Vilsmeier-Haack reagent into the system, stirring and refluxing for 12 hours under the protection of nitrogen, adding distilled water to quench the mixture after the reaction is finished, adjusting the pH to be neutral, extracting and drying, removing the solvent, and carrying out column chromatography to obtain a target product; step 3 preparation of Probe (E) -2-cyano-3- (10-ethyl-10H-phenothiazin-3-yl) -N, N-dimethylacrylamide: dissolving a proper amount of 10-ethyl-10H-phenothiazine-3-formaldehyde in ethanol, adding 2-cyano-N, N-dimethylacetamide in the same molar ratio, adding piperidine, stirring and refluxing for 8 hours under the protection of nitrogen, extracting and drying after the reaction is finished, removing the solvent, and carrying out column chromatography to obtain the target product.
3. The use of a phenothiazine-based reversible fluorescent probe as claimed in claim 1, wherein the Cys, Hcy, GSH are differentiated as follows: after the probe (10 μ M) in a PBS (pH = 7.4) buffer solution containing 1% DMSO responded to Cys (200 μ M), Hcy (15 μ M) and GSH (5 mM) for 35 min, the probe showed almost no significant change in Cys and Hcy from the ultraviolet absorption spectrum, but showed significant response to GSH, and the peaks at 310 nm and 435 nm were significantly reduced; after the probe reacts with GSH, the fluorescence intensity of the probe is obviously reduced, and the probe has almost no obvious change to Cys and Hcy.
4. The use of a phenothiazine-based reversible fluorescent probe of claim 1, wherein the titration and detection lines of the probe with GSH are determined as follows: monitoring the fluorescence intensity at 606 nm after reaction of the probe (10 μ M) with GSH in PBS (pH 7.4, 1% DMSO) (1-10 mM) over a concentration range of 0-10 mM of GSH; as the concentration of GSH increases, the fluorescence intensity of the emission peak at 606 nm also decreases; according to the test result, the probe is linearly fitted with the concentration of GSH (0-5 mM), and the fluorescence intensity and the concentration of GSH are in a linear relation when the concentration of GSH is less than 5mM, and the linear equation is y = -147.11x + 764.89; when the GSH concentration reached 5mM, the fluorescence intensity remained within a relatively stable range with almost no change in fluorescence intensity, and the lowest detection limit for GSH was calculated to be 1.07. mu.M (0-10 mM for GSH in cells).
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| CN115232089A (en) * | 2022-07-04 | 2022-10-25 | 洛阳师范学院 | Vinylphenol thiazine fluorescent probe and preparation method and application thereof |
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