CN115650900B - High-selectivity sensitive nickel ion detection fluorescent probe, preparation method and application - Google Patents
High-selectivity sensitive nickel ion detection fluorescent probe, preparation method and application Download PDFInfo
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- CN115650900B CN115650900B CN202211378703.9A CN202211378703A CN115650900B CN 115650900 B CN115650900 B CN 115650900B CN 202211378703 A CN202211378703 A CN 202211378703A CN 115650900 B CN115650900 B CN 115650900B
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Abstract
The invention relates to a high-selectivity nickel ion fluorescent probe, and provides an effective and simple method for detecting nickel ions. Specifically, the probe of the invention is a quinoline salt derivative compound, which can be used as a nickel ion fluorescent probe for detecting nickel ions. Such probes may achieve at least one of the following technical effects: high selectivity for recognition of nickel ions; the sensitivity detection of nickel ions can be realized; the quantitative analysis of nickel ions can be accurately carried out; the property is stable; can be stored for a long time; can also be used for detecting nickel ions in living cells and zebra fish.
Description
Technical Field
The invention relates to a benzoindole derivative compound which is used as a nickel ion fluorescent probe, can be used for specifically identifying nickel ions in quick response or can be used for measuring the concentration of nickel ions in a sample and can be used for detecting the nickel ions in living cells or zebra fish; the invention also provides a method for preparing the fluorescent probe.
Background
Nickel is a trace element essential to the human body and mainly derived from vegetables, cereal foods, kelp, and the like. However, with the continuous improvement of the requirements of people on life quality, various purifying water dispensers are popular, but after the water dispensers repeatedly heat water, the nickel ion content is increased, and the excessive nickel intake of human bodies can be caused by the repeated use of metal tableware. Normally, the nickel content in human blood is about 0.11ug/ml, and when the nickel content is higher than the normal standard, the human health is seriously jeopardized. The biggest harm of nickel to human body is skin, which directly affects the color of skin, and causes contact dermatitis. After the skin is contacted with nickel, the skin is subjected to severe itching as the first symptom, then pimples, herpes and erythema appear, and even the patients with severe illness state have inflammatory reactions such as fester, suppuration and the like.
It has been reported that hair whitening, trachoma, chronic pharyngitis and the like are liable to occur after long-term contact with nickel, and that the combined toxic effect of low-concentration nickel and its compounds with hydrochloric acid, ammonia and the like is greater, and dermatitis, tracheitis and pneumonia are caused by skin mucous membrane, respiratory tract and the like. Nickel has carcinogenicity and in 1990, nickel compounds were listed as a class of carcinogens by the world health organization's subordinate International cancer research institute. Nickel has a stimulating and damaging effect on the lung and respiratory tract, and popular medical research shows that nickel compounds can cause nose cancer and lung cancer of nickel smelting workers, and nickel with higher content in cigarettes can combine with carbon monoxide in smoke to form nickel tetracarbonyl, so that smokers are more prone to lung cancer. The nickel content in leukemia human serum is 2-5 times that of healthy human, and the disease degree is obviously related to the nickel content in serum, which suggests that nickel is also one of the causative factors of leukemia. Due to the hazard of nickel ions and importance in biological systems, the nickel ion is a target for Ni 2+ There is an increasing need for monitoring and quantifying nickel, and a sensitive method for detecting nickel is sought in order to realize the aim of nickel in living bodies and in environmentsIn-situ detection of ions provides a new direction for exploring the physiological and pathological processes of the ions.
In recent years, methods for detecting nickel ions have been reported to include atomic absorption spectrometry, flame atomic absorption spectrometry, inductively coupled plasma emission spectrometry, inductively coupled plasma mass spectrometry, spectrophotometry, and fluorescent probe analysis, among which fluorescent probes are focused on by researchers because of their unique advantages such as high selectivity, ultrasensitivity, and simplicity in synthesis. The currently reported fluorescent probe analysis methods still have certain defects such as low sensitivity, poor selectivity, poor water solubility, complex synthesis and the like. Therefore, the development of a highly selective and highly sensitive nickel ion fluorescent probe is an urgent problem to be solved.
Disclosure of Invention
The field is urgently required to prepare a simple high-selectivity ultrasensitive nickel ion fluorescent probe so as to be capable of effectively detecting nickel ions. Therefore, the novel nickel ion fluorescent probe is synthesized, has the advantages of simple synthesis, good selectivity and high sensitivity, can specifically identify nickel ions, and can be used as the nickel ion fluorescent probe to more accurately realize the detection of the nickel ions. Specifically, the invention provides a novel nickel ion fluorescent probe which is an indole salt derivative compound and has the following structure:
wherein: r is R 1 ，R 2 ，R 3 ，R 4 And R is 5 Is independently selected from the group consisting of a hydrogen atom, a linear or branched alkyl group, a sulfonic acid group, an ester group, and a hydroxyl group; and wherein R is 1 ，R 2 ，R 3 ，R 4 ，R 5 And R is 6 May be the same or different.
In some embodiments of the invention, the fluorescent probe of the invention is R 1 ，R 2 ，R 3 ，R 4 ，R 5 And R is 6 The compounds of formula (II) which are all hydrogen atoms have the following structural formula:
the invention also provides a preparation method of the fluorescent probe of the formula (I), which takes the compounds of the formula (III) and the formula (IV) as raw materials and carries out reaction preparation according to the following reaction route:
in some embodiments of the invention, specific preparation steps are as follows: dissolving the compounds of the formula (III) and the formula (IV) in acetonitrile solution, adding piperazine with a certain molar ratio, heating and refluxing under the protection of nitrogen, after the reaction is finished, vacuum filtering to obtain filtrate, evaporating the solvent under the condition of reduced pressure, obtaining a crude product, and separating the crude product by using dichloromethane to obtain the pure compound of the formula (I).
In some embodiments of the present invention, wherein the molar ratio of the compounds of formula (III) to formula (IV) is from 1:1 to 1:3.
In some embodiments of the present invention, wherein the reflux time is 6 hours.
The invention also provides a fluorescent probe composition for measuring, detecting or screening nickel ions, which comprises the fluorescent probe of the formula (I) or the formula (II).
In some embodiments of the invention, the fluorescent probe composition further comprises a solvent, an acid, a base, a buffer solution, or a combination thereof.
The present invention also provides a method for detecting the presence of nickel ions in a sample or determining the nickel ion content in a sample, comprising:
a) Contacting a fluorescent probe of formula (I) or formula (II) with a sample to form a fluorescent compound;
b) Determining the fluorescent properties of the fluorescent compound.
In some embodiments of the invention, the sample is a water sample, a chemical sample, or a biological sample.
The invention also provides application of the fluorescent probe of the formula (I) or the formula (II), and the fluorescent probe is used for preparing a reagent applied to detection or real-time detection of nickel ions in organisms.
The invention also provides application of the fluorescent probe of the formula (I) or the formula (II) in cell fluorescence imaging.
The invention also provides a detection preparation or kit for detecting the concentration of nickel ions in a sample, which comprises the fluorescent probe of the formula (I) or the formula (II).
Compared with the prior art, the invention has the following remarkable advantages and effects:
(1) Short response time and high sensitivity
The fluorescent probe provided by the invention has the advantages of sensitive reaction with nickel ions, low detection limit of 17nM, rapid reaction and capability of reaching a platform in three minutes, thereby realizing rapid detection of nickel ions, and being particularly applicable to detection of nickel ions in organisms.
(2) High selectivity and high anti-interference ability
The fluorescent probe of the invention can selectively react with nickel ions specifically to generate fluorescent change
Compared with common other metal ions such as silver ions, aluminum ions, chromium ions, copper ions, ferrous ions, ferric ions, magnesium ions, manganese ions, sodium ions, lead ions, tin ions, zinc ions, potassium ions and the like, the fluorescent probe of the invention has higher selectivity and strong anti-interference capability.
(4) Low cytotoxicity, and can be applied under physiological level
The fluorescent probe provided by the invention has low cytotoxicity, is favorable for application under physiological level conditions, and can be applied to living cell fluorescence imaging.
(5) Can be applied under physiological level
The nickel ion fluorescent probe can be applied under the physiological level condition, and the interference of common metal ions in organisms on the nickel ion fluorescent probe is small, so that the nickel ion fluorescent probe can be applied to living cell fluorescent imaging.
(6) Good stability
The nickel ion fluorescent probe has good stability, and can be stored for a long time.
(7) Simple synthesis
The nickel ion fluorescent probe is simple to synthesize and is favorable for commercialized popularization and application.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, it being obvious that the drawings in the following description are only some embodiments of the invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a time kinetic profile of probe (5. Mu.M) versus nickel ion (10. Mu.M) at 575 nm;
FIG. 2 is an absorption spectrum of a probe (5. Mu.M) before and after addition of nickel ions (5. Mu.M, 10. Mu.M);
FIG. 3 is a fluorescence spectrum of a probe (5. Mu.M) before and after addition of nickel ions (0-10. Mu.M);
FIG. 4 is a graph showing the linear relationship between the fluorescence intensity of a probe (5. Mu.M) at 575nm and nickel ions (0-4. Mu.M);
FIG. 5 is the effect of nickel ions (10. Mu.M) and other different ionic analytes (25. Mu.M) on the fluorescence intensity of the probe (5. Mu.M) and the fluorescence intensity of the probe (5. Mu.M) after recognition of nickel ions (5. Mu.M) in the presence of different ionic analytes (25. Mu.M);
FIG. 6 is a fluorescence microscopic image of the probe (10. Mu.M) for exogenous nickel ions in HeLa cells;
FIG. 7 is a fluorescent microscopic image of exogenous nickel ions in zebra fish with a probe (10. Mu.M).
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it should be apparent that the described embodiments are only some of the embodiments of the present invention and should not be used to limit the protection scope of the present invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the present invention without making any inventive effort, are intended to fall within the scope of the present invention.
EXAMPLE 1 Synthesis of Compound of formula (II)
The synthetic route is as follows:
the specific operation steps are as follows:
embodiment 1: the compound of the formula (V) (252 mg,1 mmol), the compound of the formula (VI) (162 mg,1 mmol) and anhydrous piperazine (129 mg,1.5 mmol) were dissolved in 15ml of acetonitrile, and reacted under heating and refluxing conditions under nitrogen for 6 hours, and after the reaction, the solid was obtained by suction filtration under reduced pressure, whereby a crude product was obtained. The crude product was dissolved in dichloromethane to remove soluble impurities to give 210mg of the pure compound in a violet color with a yield of 53.0%.
Embodiment 2: the compound of the formula (V) (252 mg,1 mmol), the compound of the formula (VI) (243 mg,1.5 mmol) and anhydrous piperazine (129 mg,1.5 mmol) were dissolved in 15ml of acetonitrile, and reacted under heating reflux under nitrogen for 6 hours, and after the reaction, the solid was obtained by suction filtration under reduced pressure, whereby a crude product was obtained. The crude product was dissolved in dichloromethane to remove soluble impurities to give 230mg of pure brown compound in 58.1% yield.
Embodiment 3: the compound of the formula (V) (252 mg,1 mmol), the compound of the formula (VI) (324 mg,2 mmol) and anhydrous piperazine (129 mg,1.5 mmol) were dissolved in 15ml of acetonitrile, and reacted under heating and refluxing conditions under nitrogen for 6 hours, and after the reaction, the solid was obtained by suction filtration under reduced pressure, whereby a crude product was obtained. The crude product was dissolved in dichloromethane to remove soluble impurities to give 242mg of pure brown compound in 61.1% yield.
Embodiment 4: the compound of the formula (V) (252 mg,1 mmol), the compound of the formula (VI) (405 mg,2.5 mmol) and anhydrous piperazine (129 mg,1.5 mmol) were dissolved in 15ml of acetonitrile, and reacted under heating reflux under nitrogen for 6 hours, and after the reaction, the solid was obtained by suction filtration under reduced pressure, whereby a crude product was obtained. The crude product was dissolved in dichloromethane to remove soluble impurities to give 256mg of pure brown compound in 64.6% yield.
Embodiment 5: the compound of the formula (V) (252 mg,1 mmol), the compound of the formula (VI) (4816 mg,3 mmol) and anhydrous piperazine (129 mg,1.5 mmol) were dissolved in 15ml of acetonitrile, and reacted under heating and refluxing conditions under nitrogen for 6 hours, and after the reaction, the solid was obtained by suction filtration under reduced pressure, whereby a crude product was obtained. The crude product was dissolved in dichloromethane to remove soluble impurities to give 282mg of pure brown compound in 71.2% yield.
Example 2: testing of time dynamics of fluorescent probes
A10 mL test system with a probe concentration of 5. Mu.M was prepared, then 10. Mu.M nickel ions were added to the test system, and immediately after shaking, the change in fluorescence intensity was measured by a fluorescence spectrometer. The above measurement was performed in an acetonitrile and aqueous solution (v/v 3:7) system using the probe prepared in example 1, and the fluorescence spectrum was measured at 25℃and the test results are shown in FIG. 1.
As is clear from FIG. 1, when nickel ions are added, the fluorescence intensity reaches a maximum value in three minutes and remains unchanged, which indicates that the probe reacts rapidly with nickel ions and can provide a rapid analysis method for the determination of nickel ions.
Example 3 testing absorbance spectra of fluorescent probes before and after Nickel ion addition
Two 5mL test systems were prepared, labeled A and B. Test system B served as a control group without any manipulation. After adding a probe (5. Mu.M) to the test system A, measurement was performed by an ultraviolet absorption spectrometer, and then nickel ions (5. Mu.M, 10. Mu.M) were added to the test system A, respectively, and measurement was performed by an ultraviolet absorption spectrometer. The above measurement was performed in an acetonitrile and aqueous solution (v/v 3:7) system using the probe prepared in example 1, and the fluorescence spectrum was measured at 25℃and the test results are shown in FIG. 2.
As is clear from fig. 2, the absorption peak of the probe changes significantly when nickel ions are added.
Example 4: testing concentration gradient of fluorescent probe to Nickel ion
A plurality of parallel samples with the probe concentration of 5 mu M are arranged in a 10mL colorimetric tube, then nickel ions (0-10 mu M) with different concentrations are added into a test system, and after uniform shaking, a fluorescence spectrometer is used for testing the change of fluorescence intensity. The above assay was performed in an acetonitrile and aqueous solution (v/v 3:7) system using the probe prepared in example 1, and fluorescence spectra were measured at 25℃and the test results are shown in FIGS. 3 and 4.
As is clear from fig. 3, the fluorescence intensity at 575nm gradually decreases as the nickel ion concentration increases. Also, as can be seen from FIG. 4, after the probe (5. Mu.M) was added with nickel ions (0-4. Mu.M), a good linear relationship was exhibited between the fluorescence intensity at 575nm and the concentration of nickel ions, which demonstrated that quantitative analysis of nickel ions was possible by means of the fluorescent probe.
Example 5: testing the selectivity and anti-interference performance of fluorescent probes
A plurality of parallel samples with the probe concentration of 5 mu M are arranged in a 10mL colorimetric tube, then different analytes (the analytes are respectively blank, silver ion, aluminum ion, chromium ion, copper ion, ferrous ion, ferric ion, magnesium ion, manganese ion, sodium ion, lead ion, tin ion, zinc ion, potassium ion and nickel ion, the concentrations of other analytes are 25 mu M except for the nickel ion, and the concentration of the other analytes is 25 mu M) are added into a test system, and a fluorescence spectrometer is used for testing the fluorescence intensity change after the analytes are uniformly shaken. The above measurement was performed in an acetonitrile and aqueous solution (v/v3:7) system using the probe prepared in example 1, and the fluorescence spectrum was measured at 25℃and the test results are shown in the right bar chart of each set of bar charts in FIG. 5.
As is clear from fig. 5, only the addition of nickel ions causes a strong change in the fluorescence intensity of the probe, while the effect of other analytes is almost negligible. Experiments prove that the probe has higher selectivity on nickel ions, and is favorable for detection and analysis of the nickel ions.
A plurality of parallel samples with the probe concentration of 5 mu M are arranged in a 10mL colorimetric tube, then different analytes (the analytes are blank, silver ion, aluminum ion, chromium ion, copper ion, ferrous ion, ferric ion, magnesium ion, manganese ion, sodium ion, lead ion, tin ion, zinc ion, potassium ion and nickel ion respectively, the concentrations of other analytes are 25 mu M except for the nickel ion, the concentration of the other analytes is 25 mu M) are added respectively except for the first blank group after shaking uniformly, and the fluorescence intensity change is tested by a fluorescence spectrometer after shaking uniformly. The above assay was performed in an acetonitrile and aqueous (v/v 3:7) system using the probe prepared in example 1 and fluorescence spectra were measured at 25℃as shown in the left bar graph of each set of bar graphs in FIG. 5.
As can be clearly seen from FIG. 5, the addition of other metal ions hardly interferes with the detection of nickel ions by the fluorescent probe, and experiments prove that the probe has higher anti-interference capability on nickel ions and is beneficial to the detection and analysis of nickel ions.
Example 6: fluorescent probe fluorescence microscopy imaging of exogenous nickel ions in HeLa cells
HeLa cells were divided into three groups, group A as control group, incubated with probe alone (10. Mu.M) for 20min; group B was incubated with probe (10. Mu.M) for 20min followed by nickel ion (10. Mu.M) for 20min; group C was incubated with probe (10. Mu.M) for 20min followed by nickel ion (20. Mu.M) for 20min; finally, confocal microscopy imaging was performed on each of the three groups of cells, and the test results are shown in fig. 6.
As can be seen from FIG. 6, the background fluorescence intensity of the probe is lower, and the fluorescence intensity is enhanced along with the enhancement of the concentration of nickel ions, and experimental results prove that the probe can detect exogenous nickel ions in HeLa cells.
Example 7: fluorescent probe fluorescence microscopic imaging of exogenous nickel ions in zebra fish
Zebra fish cells were divided into three groups, group a as a control group, incubated with probe alone (10 μm) for 20min; group B was incubated with probe (10. Mu.M) for 20min followed by nickel ion (10. Mu.M) for 20min; group C was incubated with probe (10. Mu.M) for 20min followed by nickel ion (20. Mu.M) for 20min; finally, confocal microscopic imaging is carried out on the three groups of zebra fish respectively, and the test results are shown in fig. 7.
As can be seen from fig. 7, with the increase of the concentration of nickel ions, the fluorescence intensity in the zebra fish body is also increased, and as can be seen from fig. 7, the probe can detect exogenous nickel ions in zebra fish cells; experiments prove that the probe can be applied to nickel ion detection in biological samples.
While the invention has been described with reference to the above embodiments, it will be understood that the invention is capable of further modifications and variations without departing from the spirit of the invention, and these modifications and variations are within the scope of the invention.
Claims (9)
1. A fluorescent probe for measuring, detecting or screening nickel ions, characterized in that: the chemical structural formula is shown as formula (II):
2. a method of preparing the fluorescent probe of claim 1, comprising the steps of:
the quinoline salt (V) and the compound (VI) are used as raw materials and are prepared by the following reaction route:
3. the method of manufacturing according to claim 2, comprising the steps of:
dissolving the compound of the formula (V) and the formula (VI) in acetonitrile solution, adding piperazine with a certain molar ratio, heating and refluxing under the protection of nitrogen, after the reaction is finished, vacuum filtering to obtain filtrate, and evaporating the solvent under the condition of reduced pressure to obtain a crude product, and separating the crude product by using dichloromethane to obtain the pure compound of the formula (II).
4. A fluorescent probe composition for measuring, detecting or screening nickel ions comprising the fluorescent probe of claim 1.
5. The fluorescent probe composition of claim 4, further comprising a solvent, an acid, a base, a buffer solution, or a combination thereof.
6. A method for detecting the presence of nickel ions in a sample or determining the nickel ion content in a sample, comprising:
a) Contacting the fluorescent probe of claim 1 with a sample to form a fluorescent compound;
b) Determining the fluorescent properties of the fluorescent compound.
7. The method of claim 6, wherein the sample is a water sample, a chemical sample, or a biological sample.
8. Use of a fluorescent probe according to claim 1, characterized in that: the fluorescent probe is used for preparing a reagent for detecting or detecting nickel ions in organisms in real time for non-therapeutic or diagnostic purposes.
9. Use of a fluorescent probe according to claim 1 for fluorescence imaging of cells for non-therapeutic or diagnostic purposes.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107253932A (en) * | 2017-05-26 | 2017-10-17 | 济南大学 | A kind of quick high-selectivity hypersensitive nickel ion ratio fluorescent probe and preparation method thereof |
| CN112409238A (en) * | 2020-11-13 | 2021-02-26 | 山东师范大学 | Benzoindole compound, preparation method and application thereof in detection of cysteine |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107253932A (en) * | 2017-05-26 | 2017-10-17 | 济南大学 | A kind of quick high-selectivity hypersensitive nickel ion ratio fluorescent probe and preparation method thereof |
| CN112409238A (en) * | 2020-11-13 | 2021-02-26 | 山东师范大学 | Benzoindole compound, preparation method and application thereof in detection of cysteine |
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