CN111484470A - Fluorescent probe for detecting hydrazine, preparation method and application thereof - Google Patents
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Abstract
The invention provides a fluorescent probe for detecting hydrazine, which has a chemical structural formula as follows:
(ii) a The invention also provides a preparation method and application of the fluorescent probe, and develops the synthesis of the fluorescent probe responding to hydrazine, so that the detection of hydrazine in a biological system is realized, and the maximum absorption is at 406 nm; n prepared by the invention2H4Probe, with addition of 0-50 equivalents of hydrazine, with N2H4The increasing fluorescence of the added equivalent progressively indicates that the N prepared by the invention2H4The probe has wide detection range and high sensitivity on the concentration of hydrazine; n prepared by the invention2H4Probe, 10. mu.MWhen 20 equivalents of hydrazine is added at the concentration, the fluorescence intensity rapidly reaches the maximum with the increase of time, and N is realized2H4The fluorescence intensity basically shows linear increase along with the time increase and reaches the maximum value at 125min when the detection is carried out for 0-40 min.
Description
Technical Field
The invention relates to a fluorescent probe for detecting hydrazine, and a spectrum test and a cell imaging method; belonging to the field of organic small molecule fluorescent probes.
Background
Hydrazine (also known as hydrazine, anhydrous hydrazine, formula N)2H4) The material is widely applied to the fields of medicine, chemical engineering, military affairs, aerospace and the like, and is used for manufacturing isoniazid, photographic developing medicaments, jet engine fuel, rocket fuel, antioxidants, reducing agents, high-pressure boiler water supply deoxidizers and the like, but hydrazine is toxic to blood and nervous systems of human bodies, the toxicity can be accumulated for a long time, the hydrazine is extremely toxic, and L D is orally taken by mice50At 59mg/kg, was administered intravenously L D50It was 57 mg/kg. Hydrazine has become a recognized carcinogen and is also one of the important harmful substances in the environment.
At present, the hydrazine is detected by a commonly used method such as a chromatographic method, an electrochemical method, a spectrophotometric method, a chemical titration method and the like. The fluorescence spectrum analysis method has the advantages of simple operation, high sensitivity, strong specificity, good biocompatibility and the like.
The existing organic small molecular fluorescent probe is shown in N2H4The detection of (2) has the defects of long response time and single recognition site.
Disclosure of Invention
Aiming at the existing organic small molecule fluorescent probe in N2H4The invention synthesizes a hydrazine fluorescent probe with new recognition sites and high selectivity by molecular design, and the hydrazine fluorescent probe is used for detecting the N-type fluorescent probe2H4The response time is fast.
In order to solve the technical problems, the invention adopts the following technical scheme:
a fluorescent probe for detecting hydrazine, wherein the chemical structural formula of the fluorescent probe is as follows:
the following is a further improvement of the above technical solution:
a preparation method of a fluorescent probe for detecting hydrazine comprises the steps of preparing an intermediate product from a compound 1 and a compound 2, and then reacting the intermediate product with acetyl chloride to prepare the fluorescent probe.
The chemical structural formula of the compound 1 is as follows:
the chemical structural formula of the compound 2 is as follows:
the chemical structural formula of the intermediate is as follows:
probe Cou-L yso-N2H4The synthetic route of (2) is as follows:
dissolving the compound 1 in absolute ethyl alcohol, adding triethylamine and the compound 2, and heating under reflux for 6-9 hours; the molar ratio of the compound 1 to the compound 2 is 1: 1.1-1.3; the molar ratio of the compound 1 to triethylamine is 1: 1.1-1.3; the mass-volume ratio of the compound 1 to the absolute ethyl alcohol is 10-11 mg/ml.
The preparation of the fluorescent probe comprises the steps of dissolving an intermediate product in dichloromethane, adding triethylamine, stirring in an ice water area, then dropwise adding acetyl chloride, moving to room temperature, and stirring until the reaction is finished.
The molar ratio of the intermediate product to acetyl chloride is 1: 1.1-1.3; the molar ratio of the intermediate product to triethylamine is 1: 1.1-1.3; the mass-to-volume ratio of the intermediate product to the dichloromethane is 12-13 mg/ml.
The preparation of the probe preferably comprises the following steps:
the synthesis of the probe is carried out in two steps:
compound 1 (0.5 mmol, 103.1 mg) was dissolved in absolute ethanol (10.0 m L), triethylamine (0.6 mmol, 60.7 mg) and compound 2 (0.6 mmol, 78.1 mg) were added, heating under reflux for 8 hours, the reaction mixture was cooled, the precipitate was filtered, the solution was extracted with dichloromethane and water, the organic layers were combined, dried over anhydrous sodium sulfate and concentrated to give crude compound Cou-L yso column chromatography to give compound Cou-L yso.
Dissolving Cou-L yso (0.2 mmol, 63.6 mg) in dichloromethane (5.0 m L), adding triethylamine (0.24 mmol, 24.3 mg), stirring in ice water, adding acetyl chloride (0.24 mmol, 18.8 mg) dropwise into the above reaction, stirring at room temperature until the reaction is completed, cooling the reaction, adding water to quench, extracting with dichloromethane and water, drying, concentrating, and performing column chromatography to obtain probe Cou-L yso-N2H4。
Application of fluorescent probe for detecting hydrazine in water environment and biological system2H4Sensing and detecting; the sensing detection comprises fluorescence detection, cell imaging and hydrazine detection in the environment.
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention develops the synthesis of a fluorescent probe responding to hydrazine, realizes the detection of hydrazine in a biological system, and has the maximum absorption at 406 nm.
(2) N prepared by the invention2H4Probe, 0-50 equivalents (0-500. mu.M) of hydrazine added with N2H4The increasing fluorescence of the added equivalent progressively indicates that the N prepared by the invention2H4The probe has wide detection range and high sensitivity to the concentration of hydrazine.
(3) N prepared by the invention2H4Probe, 20 equivalents of hydrazine are added at 10. mu.M concentration, the fluorescence intensity rapidly reaches the maximum with the increase of time, and the realization ofN2H4The fluorescence intensity basically shows linear increase along with the time increase within 0-40min, and reaches the maximum value at 125min, which shows that the N of the invention2H4The probe, when used for detecting hydrazine, has short response time.
(4) The invention realizes N2H4The molecular probe has the advantages of rapid detection selectivity, good selectivity and strong anti-interference ability of other ions. Based on its specific and remarkable color change, the reagent can be used for neutralizing N in biological cells as display aqueous solution2H4The specific indicator of the existence of the molecule can carry out real-time qualitative visual colorimetric detection.
(5) The synthesis of the probe can be completed by only two steps, and the post-treatment process is simple; thus, the present invention is a simple, fast, sensitive N2H4The molecular specificity detection reagent has wide application prospect in the field of biomolecule detection.
The properties of which will be described in detail in the examples with reference to the accompanying drawings.
Drawings
FIG. 1 shows probes Cou-L yso-N in example 12H4Is/are as follows1H NMR spectrum;
FIG. 2 shows probes Cou-L yso-N2H4An absorption spectrum;
FIG. 3 shows probes Cou-L yso-N2H4With different equivalent weights of N2H4The change in added fluorescence intensity of (1);
FIG. 4 shows probes Cou-L yso-N2H4Change in fluorescence intensity over time;
FIG. 5 shows probes Cou-L yso-N2H4Selective histogram data;
in FIG. 5, ions Nos. 1 to 15 are added: 1: none; 2: n is a radical of2H4；3：Al3+；4：ALA；5：Ca+；6：Cl-；7：CO3 2-；8：Cu2+；9：Cys；10：GSH；11：I-；12：K+；13：Mg2+； 14:Na+；15:SO3 2-；
FIG. 6 shows probes Cou-L yso-N2H4Application to N in cells2H4Fluorescence imaging of (2).
Detailed Description
The invention is further illustrated by the following examples and figures, but is not limited by the following examples, which are numbers of compounds in the examples that are given in relation to the numbers of compounds in the schemes above.
Example 1 Probe Compound Cou-L yso-N2H4The synthesis of (2):
(1) preparation of Compounds Cou-L yso
Compound 1 (0.5 mmol, 103.1 mg) was dissolved in absolute ethanol (10.0 m L), triethylamine (0.6 mmol, 60.7 mg) and compound 2 (0.6 mmol, 78.1 mg) were added, heating was performed under reflux for 8 hours, the reaction mixture was cooled, the precipitate was filtered, the solution was extracted with dichloromethane and water, the organic layers were combined, dried over anhydrous sodium sulfate, concentrated to give crude compounds Cou-L yso, and column chromatography gave compounds Cou-L yso.
(2) Preparation of Probe
Dissolving Cou-L yso (0.2 mmol, 63.6 mg) in dichloromethane (5.0 m L), adding triethylamine (0.24 mmol, 24.3 mg), stirring in ice water, adding acetyl chloride (0.24 mmol, 18.8 mg) dropwise to the reaction, stirring at room temperature until the reaction is completed, cooling the reaction, adding water to quench, extracting with dichloromethane and water, drying, concentrating, and performing column chromatography to obtain probe Cou-L yso-N2H4。
1H NMR (400 MHz, CDCl3): 9.09 (s, 1H), 8.7 (s, 1H), 7.88 (d,J= 6.8Hz, 1H), 7.21 (d,J= 1.6 Hz, 1H), 7.15 (dd,J 1 = 2.0 Hz,J 2 = 6.8 Hz, 1H),3.76 (t,J= 3.6 Hz, 4H), 3.59 (dd,J 1 = 4.4,J 2 = 8.8, 2H), 2.61 (s, 2H),2.53(s, 4H) , 2.36(s, 3H)。
Example 2 Probe Compound Cou-L yso-N2H4Absorption spectrum of
The probe Cou-L yso-N prepared in example 1 was used2H4Dissolving in N, N-Dimethylformamide (DMF) to obtain 1 mmol/L stock solution, adding 30 μ L two parts from the stock solution into a centrifuge tube with 5m L, diluting with PBS buffer solution (0.1 mol/L, pH = 7.4) and DMSO at a volume ratio of 1:1 to 3 m L, and adding N with different equivalent (0-50 equiv) to obtain N-Dimethylformamide (DMF) solution2H4Standard solution, reaction 2h for spectroscopic testing. As shown in fig. 2. Adding N2H4The maximum absorption of the rear probe is at 406 nm.
Example 3 Probe Compound Cou-L yso-N2H4With N2H4Change in fluorescence spectrum of increase of addition equivalent
The probe Cou-L yso-N prepared in example 1 was used2H4Dissolving in dimethyl sulfoxide (DMSO) to obtain 1 mmol/L stock solution, taking out 30 μ L from the stock solution, adding into 5m L centrifuge tube, adding N with different equivalent (0-100 equiv)2H4Standard solutions, diluted to 3 m L with PBS buffer (0.1 mol/L, pH = 7.4) in a volume ratio of 1:4 DMSO, were measured for fluorescence properties. fluorescence spectra are shown in FIG. 3. it can be seen from FIG. 3 that as N increases2H4The fluorescence increased gradually when equivalent weight of N was added to 50 equivalent (500. mu.M)2H4At this time, the fluorescence of the system was saturated.
Example 4 Probe Cou-L yso-N2H4Change of fluorescence spectrum with time
30 μ L from the fluorescent probe stock solution in example 1 was added to a 5m L centrifuge tube, and N was added2H4(20equiv) Standard solution, diluted to 3M L (10. mu.M) in DMSO/PBS (1:4, v/v), measured for fluorescence properties, the fluorescence spectrum is shown in FIG. 4, as can be seen from FIG. 4, probes Cou-L yso-N are added2H4Then, N is added directly2H4The fluorescence intensity rapidly reaches with the increase of timeAt maximum, realize N2H4Detection of (3).
Example 5 selectivity of fluorescent probes Cou-L yso-N2H 4 for different ions
30 μ L from the fluorescent probe stock solution in example 1 was added to 5m L centrifuge tubes, and equimolar amounts of competitor standard solutions were added, one of them being added with equimolar amounts of N2H4The fluorescence emission spectrum change of the standard solution is detected after 120 min, and other interfering ion pair compounds Cou-L yso-N can be found from figure 52H4Has little effect on the fluorescence of (2), and N2H4Addition of the solution led to compound Cou-L yso-N2H4The fluorescence of (a) is significantly enhanced.
Example 6 Cou-L yso-N2H 4 fluorescent Probe imaging N2H4 fluorescence in cells
We applied the probes of the invention to N in He L a cells2H4The detection is carried out by the application of fluorescence imaging (figure 6) the specific operation steps are that a) 20 mu M probe DMSO solution is added into the culture solution with He L a cells to be cultured for 0.5 h in a carbon dioxide incubator, bright field imaging is carried out, the approximate outline of the cells can be seen, b) a) blue light is used for excitation and observation to obtain an imaging image, c) the images of a) and b) are superposed, d) 20 mu M probe DMF solution is added into the culture solution with He L a cells to be cultured for 0.5 h in the carbon dioxide incubator, and N is added2H4Then, bright field imaging is carried out, and the approximate outline of the cell can be seen; e) carrying out excitation observation on d) by using blue light to obtain an imaging picture; f) superimposing the d) and e) image images. Shows that the fluorescent probe realizes N in cells2H4Detection of (3).
Claims (9)
1. A fluorescent probe for detecting hydrazine, which is characterized in that: the chemical structural formula of the fluorescent probe is as follows:
2. a preparation method of a fluorescent probe for detecting hydrazine is characterized by comprising the following steps: and preparing an intermediate product from the compound 1 and the compound 2, and then reacting the intermediate product with acetyl chloride to prepare the fluorescent probe.
3. The method for preparing a fluorescent probe for detecting hydrazine according to claim 2, wherein the method comprises the following steps: the chemical structural formula of the compound 1 is as follows:
4. the method for preparing a fluorescent probe for detecting hydrazine according to claim 2, wherein the method comprises the following steps: the chemical structural formula of the compound 2 is as follows:
5. the method for preparing a fluorescent probe for detecting hydrazine according to claim 2, wherein the method comprises the following steps: the chemical structural formula of the intermediate is as follows:
6. the method for preparing a fluorescent probe for detecting hydrazine according to claim 2, wherein the method comprises the following steps: dissolving the compound 1 in absolute ethyl alcohol, adding triethylamine and the compound 2, and heating under reflux for 6-9 hours; the molar ratio of the compound 1 to the compound 2 is 1: 1.1-1.3; the molar ratio of the compound 1 to triethylamine is 1: 1.1-1.3; the mass-volume ratio of the compound 1 to the absolute ethyl alcohol is 10-11 mg/ml.
7. The method for preparing a fluorescent probe for detecting hydrazine according to claim 2, wherein the method comprises the following steps: the preparation of the fluorescent probe comprises the steps of dissolving an intermediate product in dichloromethane, adding triethylamine, stirring in an ice water area, then dropwise adding acetyl chloride, moving to room temperature, and stirring until the reaction is finished.
8. The method for preparing a fluorescent probe for detecting hydrazine according to claim 7, wherein the method comprises the following steps: the molar ratio of the intermediate product to acetyl chloride is 1: 1.1-1.3; the molar ratio of the intermediate product to triethylamine is 1: 1.1-1.3; the mass-to-volume ratio of the intermediate product to the dichloromethane is 12-13 mg/ml.
9. The application of a fluorescent probe for detecting hydrazine is characterized in that: the fluorescent probe is applied to N in water environment and biological system2H4Sensing and detecting; the sensing detection comprises fluorescence detection, cell imaging and hydrazine detection in the environment.
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Cited By (1)
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Application publication date: 20200804 |