CN110964022A - Fluorescent probe for detecting peroxynitrite ions and preparation method and application thereof - Google Patents
Fluorescent probe for detecting peroxynitrite ions and preparation method and application thereof Download PDFInfo
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Abstract
The invention provides a fluorescent probe for detecting peroxynitrite ions, which comprises the following components in part by weight:
. The fluorescent probe has high specificity, is not interfered by other components in the process of detecting corresponding peroxynitrite ions, can be used for real-time determination of the peroxynitrite ions in living cells, and has wide application prospect. The fluorescent probe for detecting the peroxynitrite ions in the cells has high sensitivity and good fluorescence emission spectrum characteristics, and can realize the purpose of quickly and accurately detecting the peroxynitrite ions in the cells by drawing a standard curve to measure the peroxynitrite ions in the cells.
Description
Technical Field
The invention belongs to the technical field of analytical chemistry, and particularly relates to a fluorescent probe for detecting peroxynitrite ions and application thereof.
Background
In addition to its normal physiological functions, nitric oxide is also associated with some cell and tissue damage in the body. Current evidence suggests that the product of the reaction of nitric oxide with superoxide anion is peroxynitrite ion (ONOO-). On the one hand, peroxynitrite ions can play a role in auxiliary regulation in the immune system of the body. On the other hand, peroxynitrite ion is a strongly oxidizing and potent cytotoxic substance, which is responsible for the pathological effects of nitric oxide, which can lead to DNA damage, enzyme inhibition, cell death and bacterial intoxication and can cause a range of diseases. At present, peroxynitrite ions have been found to be present in septic shock, ischemia-reperfusion injury, atherosclerosis, diabetes, senile dementia and other diseases. Through the detection research on free radicals, the method can help people to better explain the reasons of disease generation, can take effective preventive measures and reduce the damage degree of the disease to organisms, and therefore, the development of the detection on the peroxynitrite ions in cells is very necessary.
The lifetime of peroxynitrite ions in organisms is very short, resulting in normally very low steady state concentrations, whereas short lifetime and low concentration mean that the determination of peroxynitrite ions is very difficult. The existing methods for measuring free radicals mainly comprise an Electron Spin Resonance (ESR) method, a High Performance Liquid Chromatography (HPLC), a chemiluminescence method (CL) and the like, wherein a fluorescent probe analysis method has the advantages of high sensitivity, simplicity, feasibility, high selectivity, easy synthesis, small steric hindrance, many binding sites and the like. Therefore, the method has wide development space and application prospect in the detection of peroxynitrite ions.
Disclosure of Invention
The invention provides a fluorescent probe for detecting peroxynitrite ions, which has the advantages of high response speed and strong anti-interference capability.
The invention also aims to provide the application of the fluorescent probe in detecting peroxynitrite ions in a solution or in biological cells.
In order to achieve the purpose, the invention adopts the following technical scheme.
A fluorescent probe for detecting peroxynitrite ions has a chemical structural formula shown in formula (I):
formula (I).
The preparation method of the fluorescent probe comprises the following steps:
(1) β -aminopropionic acid and p-toluenesulfonyl chloride react in NaOH solution, hydrochloric acid solution is added after the reaction is finished, and the precipitated precipitate is purified to obtain a compound 1:
；
(2) 4-diethylaminoketo acid and m-hydroxyphenylpiperazine on CH3And (3) carrying out reflux reaction in COOF, and separating and purifying after the reaction is finished to obtain a compound 2:
；
(3) under the protection of nitrogen, reacting the compound 1, the compound 2, EDC, HOBT and DIEA in DMF, and separating and purifying after the reaction is finished to obtain a compound 3:
；
(4) and reacting the compound 3 with hydrazine hydrate in absolute ethyl alcohol, and separating and purifying after the reaction is finished to obtain the fluorescent probe.
The molar ratio of the β -aminopropionic acid to the p-toluenesulfonyl chloride is 1: 1.2-1.5.
In the step (1), the purification step is as follows: washing the precipitate with cold water, drying, dissolving with dichloromethane, and performing column chromatography with petroleum ether and ethyl acetate as eluent at volume ratio of 5: 1.
In the step (2), the separation and purification step comprises: the reaction mixture was concentrated to give a concentrated solution of CH at a volume ratio of 5:12Cl2MeOH is eluent and is subjected to column chromatography.
In the step (3), the separation and purification step comprises: the reaction mixture was concentrated to give a concentrated solution of CH in a volume ratio of 15:12Cl2MeOH is eluent and is subjected to column chromatography.
In the step (4), the separation and purification step comprises: the reaction mixture was concentrated to give a concentrate of CH in a volume ratio of 20:12Cl2MeOH is passed through column chromatography.
An application of the fluorescent probe in detecting peroxynitrite ions in solution and cells.
The mechanism of the invention is as follows:
the fluorescent probe can enable rhodamine derivative spiroamide to form an open-loop structure in the presence of peroxynitrite ions, generate a form with high fluorescence emission capability, and detect the peroxynitrite ions by detecting different fluorescence intensities.
The invention has the following advantages:
the fluorescent probe for detecting the peroxynitrite ions in the cells can be obtained by chemical synthesis, the synthesis process is simple and feasible, the raw materials are cheap and easy to obtain, the preparation cost is low, and the popularization is easy. The fluorescent probe for detecting the peroxynitrite ions in the cells has high specificity, is not interfered by other components in the process of detecting the corresponding peroxynitrite ions, can be used for real-time determination of the peroxynitrite ions in the living cells, and has wide application prospect. The fluorescent probe for detecting the peroxynitrite ions in the cells has high sensitivity and good fluorescence emission spectral characteristics (550-700 nm), and can be used for rapidly and accurately detecting the peroxynitrite ions in the cells by drawing a standard curve to measure the peroxynitrite ions in the cells.
Drawings
FIG. 1 is a drawing of Compound 11H NMR spectrum;
FIG. 2 is a drawing of Compound 31H NMR spectrum;
FIG. 3 shows a fluorescent probe1H An NMR spectrum;
FIG. 4 is a graph showing fluorescence spectra and linear relationship data of fluorescent probes at different concentrations of peroxynitrite ions;
FIG. 5 is the time of effect of a fluorescent probe on peroxynitrite ions;
FIG. 6 is a fluorescence spectrum of a fluorescent probe after reacting with different substances and a time response spectrum of the fluorescent probe with peroxynitrite ions;
FIG. 7 is a graph of cell activity of HepG2 cells treated with different concentrations of probe for 8 hours;
FIG. 8 is an imaging application of fluorescent probes in living cells.
Detailed Description
The present invention will be further described with reference to the following examples and drawings, but the present invention is not limited to the following examples.
EXAMPLE 1 Synthesis of fluorescent Probe
(1) β -aminopropionic acid (600 mg, 6.7 mmol) was added to distilled water (4 mL), aqueous NaOH (2M, 3.4 mL) was added, p-toluenesulfonyl chloride (1.83 g, 9.6 mmol) was then added, the reaction mixture was stirred at 35 deg.C, 1M aqueous NaOH was added to maintain pH at 9, after complete consumption of the base, stirring was carried out at 35 deg.C for one hour, unreacted p-toluenesulfonyl chloride was removed by filtration, the reaction mixture was acidified with 5M aqueous HCl at 0 deg.C to maintain pH =2, the precipitated white precipitate was filtered, washed with cold water, dissolved in dichloromethane solvent, and purified by column chromatography (petroleum ether: ethyl acetate =5:1) to give compound 1, which is compound 11The H NMR spectrum is shown in figure 1:
(2) 4-Diethylaminoketo acid (940 mg, 3 mmol), m-hydroxyphenylpiperazine (534.7 mg, 3 mmol) were dissolved in 5 mL of CH3COOF, heating reflux reaction at 90 deg.C for 12 h, vacuum concentrating the reaction mixture, and purifying by column Chromatography (CH)2Cl2MeOH =5:1 v/v) gave a red powder, compound 2, which was1H NMR chartThe spectrum is shown in FIG. 2:
(3) compound 1 (243.3 mg, 1 mmol), Compound 2 (456.6 mg, 1 mmol), EDC (383.4 mg, 2 mmol), HOBT (67.6 mg, 0.5 mmol) were dissolved in 2 mL of DMF, 200. mu.L of DIEA was added after stirring for 10min, stirred at room temperature for 5 h under nitrogen, DMF was removed by extraction with water and saturated NaCl respectively, the reaction mixture was concentrated in vacuo and purified by column Chromatography (CH)2Cl2MeOH =15:1 v/v) gave a pink powder, compound 3, which was1The H NMR spectrum is shown in FIG. 3:
(4) compound 3 (234.2 mg, 0.3 mmol), hydrazine hydrate (150.2 mg, 3 mmol) were dissolved in 10 mL of anhydrous ethanol, heated at 90 ℃ under reflux for 2 h, the reaction mixture was concentrated in vacuo, and purified by column Chromatography (CH)2Cl2MeOH =20:1 v/v) to yield a white powder, i.e., a fluorescent probe, which was obtained1The H NMR spectrum is shown in FIG. 4:
example 2 response of fluorescent probes to different concentrations of peroxynitrite ion
The fluorescent probe obtained in example 1 was prepared as a mother liquor (containing 10% acetonitrile), solutions containing peroxynitrite ions in the same volume and different concentrations were added, water was used as a blank (0. mu.M) so that the probe concentration was 5. mu.M, and fluorescence detection (lambda.: was performedex=540 nm); calculating the fluorescence intensity in each system; the probe was evaluated for its response performance to peroxynitrite ion as shown in fig. 4 (a): the probe can respond to peroxynitrite ions with the concentration of 5-200 mu M; analysis of the Linear dependence of fluorescence intensity at 581 nm on the concentration of 5-50. mu.M peroxynitrite ionAs shown in FIG. 4 (B): in the concentration range, the linear relation between the fluorescence intensity and the concentration of peroxynitrite ions is good, the linear regression equation is y =24.34x-42.64, and R = 0.9961.
Example 3 response time of fluorescent probes to peroxynitrite ion
The fluorescent probe obtained in example 1 was prepared as a mother liquor (containing 10% acetonitrile), a solution containing peroxynitrite ions was added so that the probe concentration was 5. mu.M and the peroxynitrite ion concentration was 100. mu.M, and fluorescence detection was performed every 5 seconds (. lamda.) (lambda.ex=540 nm), detecting for 10 min; calculating the fluorescence intensity in each system; the probe was evaluated for its response speed to peroxynitrite ions, as shown in fig. 5: adding ONOO-The response time is less than 5s later, which shows that the probe pair ONOO-The response is very rapid.
Example 4 selectivity of fluorescent probes for different ions
The fluorescent probe obtained in example 1 was prepared as a 5. mu.M buffer solution (containing 5% acetonitrile, pH = 7.5), and 4mL of each probe solution was added to 100. mu.L of 40 mM Hcys and Na, respectively2S、Na2SO3、NO、H2O2、Cys、NaNO2And a solution of Vc and metal ions in PBS. Then fluorescence detection (lambda) was performedex=540 nm); calculating the fluorescence intensity in each system; the interference of the different substances with the fluorescent probe solution was evaluated and the results are shown in FIG. 6, in which 1 to 17 are 1 Blank; 2. ba2+；3. Al3 +；4. Ca2+；5. Co2+；6. Na+；7. Cys；8. Fe2+；9. GSH；10. Hcy；11. Hg2+；12. K+；13. Mg2+；14. OCl-；15. CO3 2-；16. SO3 2-；17. ONOO-. Therefore, the probe provided by the invention only responds to oxygen nitrite ions, and has strong anti-interference capability.
Example 5 toxicity of fluorescent probes to cells
HepG2 cells were seeded into 96-well plates at 8000 cells per well and cultured overnight in medium (100 mL) followed by incubation for 24 hours at different concentrations of RHPN. Then 10 mL of MTT solution at a concentration of 5 mg/mL was added for 3 hours, then the medium was removed and the precipitate was dissolved in 100 mL of dimethyl sulfoxide (DMSO), and then the plate was shaken for 40 min. Finally, the absorbance of the solution at 570 nm was measured with a microplate reader to evaluate the cytotoxicity of the probe, and the results are shown in FIG. 7. As can be seen, the cell survival rate of the probe of the present invention is 85% or more in the concentration range of 1-50. mu.M, and the cytotoxicity is low.
Example 6 imaging application of fluorescent probes in Living cells
The fluorescent probe prepared in example 1 was prepared as a 10 μ M buffer solution (containing 5% acetonitrile, pH = 7.5); 3 portions of HeGp2 cells were cultured in DMEM medium (containing 10% fetal calf serum) at 37 ℃ in 5% CO2And 20% of O2Then, a portion of the fluorescent probe solution was aspirated by a microsyringe and injected into a medium containing HeGp2 cells, the incubation was continued in the incubator for 30min, and thereafter, the cultured cells were washed 3 times with PBS buffer and subjected to fluorescence imaging (lambda. fluorescence imaging)ex=561 nm); adding fluorescent probe into the other two parts, culturing for 30min, and adding 100 μ M and 200 μ M ONOO respectively-The solution was incubated in an incubator for 30min, and then the cultured cells were washed 3 times with PBS buffer and subjected to fluorescence imaging (. lamda.)ex=561 nm), the results are shown in fig. 8: HepG2 cells showed relatively weak fluorescence when ONOO was added-After solution, the red fluorescence increased and the fluorescence intensity followed the ONOO-The concentration increases.
Claims (8)
1. A fluorescent probe for detecting peroxynitrite ions has a chemical structural formula shown in formula (I):
formula (I).
2. A method of preparing a fluorescent probe according to claim 1, comprising the steps of:
(1) β -aminopropionic acid and paratoluensulfonyl chloride react in NaOH solution, hydrochloric acid solution is added after the reaction is finished, and the compound 1 is obtained by precipitation, filtration, washing and reduced pressure distillation:
；
(2) 4-diethylaminoketo acid and m-hydroxyphenylpiperazine on CH3And (3) carrying out reflux reaction in COOF, and separating and purifying after the reaction is finished to obtain a compound 2:
；
(3) under the protection of nitrogen, reacting the compound 1, the compound 2, EDC, HOBT and DIEA in DMF, and separating and purifying after the reaction is finished to obtain a compound 3:
；
(4) and reacting the compound 3 with hydrazine hydrate in absolute ethyl alcohol, and separating and purifying after the reaction is finished to obtain the fluorescent probe.
3. The preparation method according to claim 2, wherein the molar ratio of β -aminopropionic acid to p-toluenesulfonyl chloride is 1: 1.2-1.5.
4. The method according to claim 2, wherein in the step (1), the purification step is: washing the precipitate with cold water, drying, dissolving with dichloromethane, and performing column chromatography with petroleum ether and ethyl acetate as eluent at volume ratio of 5: 1.
5. The preparation method according to claim 2, wherein in the step (2), the separation and purification step is: the reaction mixture was concentrated to give a concentrated solution of CH at a volume ratio of 5:12Cl2MeOH is eluent and is subjected to column chromatography.
6.The preparation method according to claim 2, wherein in the step (3), the separation and purification step is: the reaction mixture was concentrated to give a concentrated solution of CH in a volume ratio of 15:12Cl2MeOH is eluent and is subjected to column chromatography.
7. The preparation method according to claim 2, wherein in the step (4), the separation and purification step is: the reaction mixture was concentrated to give a concentrate of CH in a volume ratio of 20:12Cl2MeOH is passed through column chromatography.
8. Use of the fluorescent probe of claim 1 for detecting peroxynitrite ions in a solution or cell.
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| CN115850314A (en) * | 2022-12-30 | 2023-03-28 | 厦门大学附属心血管病医院 | Peroxynitrite and lipid droplet dual-response probe and preparation method and application thereof |
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| CN106905235A (en) * | 2017-01-19 | 2017-06-30 | 北京师范大学 | Peroxynitrite detection probe, preparation method and applications |
| CN108164494A (en) * | 2018-02-11 | 2018-06-15 | 山东师范大学 | A kind of two-photon fluorescence probe for detecting peroxynitrite and its preparation method and application |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106905235A (en) * | 2017-01-19 | 2017-06-30 | 北京师范大学 | Peroxynitrite detection probe, preparation method and applications |
| CN108164494A (en) * | 2018-02-11 | 2018-06-15 | 山东师范大学 | A kind of two-photon fluorescence probe for detecting peroxynitrite and its preparation method and application |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115850314A (en) * | 2022-12-30 | 2023-03-28 | 厦门大学附属心血管病医院 | Peroxynitrite and lipid droplet dual-response probe and preparation method and application thereof |
| CN115850314B (en) * | 2022-12-30 | 2024-06-21 | 厦门大学附属心血管病医院 | Peroxynitrite and lipid drop dual-response probe and preparation method and application thereof |
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