CN114113045A - Novel near-infrared hydrazine hydrate fluorescence detection reagent and application thereof - Google Patents
Novel near-infrared hydrazine hydrate fluorescence detection reagent and application thereof Download PDFInfo
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- CN114113045A CN114113045A CN202010896692.8A CN202010896692A CN114113045A CN 114113045 A CN114113045 A CN 114113045A CN 202010896692 A CN202010896692 A CN 202010896692A CN 114113045 A CN114113045 A CN 114113045A
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 title claims abstract description 41
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- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 28
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- 238000001514 detection method Methods 0.000 claims abstract description 10
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims abstract description 5
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- 239000003068 molecular probe Substances 0.000 claims description 7
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- 238000004445 quantitative analysis Methods 0.000 abstract 1
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- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
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- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 101710138657 Neurotoxin Proteins 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
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- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
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- 231100000618 neurotoxin Toxicity 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/76—Chemiluminescence; Bioluminescence
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plasma & Fusion (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
The invention discloses construction and application of a novel near-infrared hydrazine hydrate fluorescence detection reagent, wherein the detection reagent is a fluorescence probe, and the chemical structural formula of the probe is as follows:
Description
Technical Field
The invention belongs to the technical field of analytical chemistry, and relates to construction and application of a novel near-infrared hydrazine hydrate fluorescence detection reagent.
Background
Hydrazine hydrate (Hydrazine, N)2H4) Is a colorless flammable liquid and has application in battery fuel and even missile and rocket propulsion systems. Meanwhile, the product is a reductive and alkalescent substance with high reaction activity, and can be widely applied to the related fields of pharmacy and pesticides as an antioxidant, a herbicide, a plant growth regulator and the like. In addition, hydrazine hydrate also plays an important role in textile dyes, corrosion protection and other fine chemical engineering.
However, hydrazine hydrate is a highly toxic chemical substance for organisms, and it is easy to cause environmental pollution such as soil and human body injury in the processes of use, transportation, storage and the like. Hydrazine hydrate, for example, is a neurotoxin which has excellent water solubility and is easily absorbed into the human body through the oral cavity or the skin, thereby seriously damaging organs and the central nervous system. The united states Environmental Protection Agency (EPA) lists hydrazine hydrate as a potential carcinogen and sets its Threshold Limit (TLV) to 10 ppb. Therefore, the development of a reliable and sensitive hydrazine hydrate real-time detection method has very important significance.
Conventional methods such as chromatography, electrochemical method, titration method and the like have been reported to be applicable to the detection of hydrazine hydrate, but the methods usually have the defects of expensive instrument and equipment, complicated pretreatment and operation process and the like. In contrast, fluorescence detection methods based on fluorescent probes are favored by researchers because of their excellent selectivity, sensitivity, and a series of advantages such as the ability to perform real-time detection in cell tissues.
A plurality of fluorescent probes have been reported at present and have excellent specificity and sensitivity, but most of them have maximum emission wavelength in ultraviolet region (400-600 nm). For example, CN 110204535 a reports that a fluorescent molecular probe of hydrazine hydrate of coumarin compounds can specifically react with hydrazine hydrate to generate changes of fluorescence spectrum, thereby realizing quantitative detection of hydrazine hydrate, but the maximum emission wavelength is 450 nm. Has larger tissue injury and smaller tissue penetrating power, is easily interfered by background fluorescence, and has easily influenced accuracy. Therefore, it is very important and necessary to develop a near infrared fluorescent probe with high sensitivity and strong specificity, which can be used for detecting hydrazine hydrate in aqueous solution and organism.
Disclosure of Invention
Aiming at the defects of the existing hydrazine hydrate fluorescent molecular probe, the invention aims to provide a near-infrared fluorescent probe which has high sensitivity and strong specificity and can be used for detecting hydrazine hydrate in aqueous solution and organisms and a high-efficiency preparation method thereof.
In order to achieve the above object, the present invention provides a fluorescence detection reagent having a structure of formula I:
the preparation method of the fluorescent probe is preferably as follows:
1) dissolving o-hydroxybenzaldehyde and DCM-CHO into absolute ethyl alcohol, adding tetrahydropyrrole as a catalyst, placing a reaction system at room temperature, and stirring until the reaction is complete, so that a large amount of red solid is separated out. And (3) carrying out suction filtration, washing with absolute ethyl alcohol for three times, and drying to obtain a compound 1.
2) Compound 1 and levulinic acid were dissolved in anhydrous dichloromethane and EDC and DMAP were added as condensing agent and catalyst. The reaction was stirred at room temperature until the reaction was complete. And (4) removing the solvent under reduced pressure, and purifying by column chromatography to obtain the target molecular probe.
The molar ratio of the o-hydroxybenzaldehyde, the DCM-CHO and the tetrahydropyrrole in the step (1) is 2:2: 1.
The molar ratio of the compound 1, the levulinic acid, the EDC and the DMAP in the step (2) is 5:10:10: 1.
The synthesis of the invention is as follows:
the mechanism of the present invention is as follows:
compared with the prior art, the technical scheme of the invention has the beneficial technical effects that:
(1) the fluorescence detection reagent provided by the invention can perform specific action with hydrazine hydrate to generate the change of fluorescence spectrum, thereby realizing the quantitative detection of the hydrazine hydrate;
(2) the fluorescence detection reagent provided by the invention can emit red fluorescence after responding to hydrazine hydrate, has strong tissue penetrating power and small tissue damage, can effectively avoid the interference of background fluorescence, and has higher accuracy;
(3) the fluorescence detection reagent provided by the invention can be synthesized only by 2 steps, has simple post-treatment and high yield, and is suitable for large-scale popularization and use.
Drawings
FIG. 1 is a fluorescence emission spectrum of the fluorescence intensity of the fluorescence detection reagent according to the variation of the hydrazine hydrate 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 reagent and the concentration of hydrazine hydrate in the practice of the present invention;
FIG. 3 is a graph showing the selectivity of a fluorescence detection reagent for hydrazine hydrate in the practice of the present invention;
FIG. 4 is a confocal image of fluorescence of the 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
O-hydroxybenzaldehyde (272.30 mg, 2 mmol) and DCM-CHO (552.57 mg, 2 mmol) were dissolved in 18 mL of anhydrous ethanol, 0.07 mL (71.12 mg, 1 mmol) of tetrahydropyrrole was added as a catalyst, the reaction system was left to stir at room temperature, TLC monitored to completion, and a large amount of red solid was precipitated. After suction filtration and washing with anhydrous ethanol three times and drying, 1605.83 mg of the compound was obtained with a yield of 76.8%.
Synthesis and structural characterization of target molecular probe
Compound 1 (394.42 mg, 1 mmol) and levulinic acid (232.23 mg, 2 mmol) are dissolved in 18 mL of anhydrous dichloromethane, and EDC (383.4 mg, 2 mmol) and DMAP (24.43 mg, 0.2 mmol) are added as the condensing agent and catalyst. The reaction was stirred at room temperature and monitored by TLC to completion. The solvent was removed under reduced pressure and purified by column chromatography to give 404.38 mg of the target molecular probe, 82.1% yield.1H NMR (400 MHz, DMSO-d6) δ 8.22 (d, J=7.9 Hz, 1H), 8.08-8.06 (m, 2H), 7.89 (d, J=7.8 Hz, 1H), 7.72-7.70 (m, 2H), 7.59 (d, J=14.6 Hz, 1H), 7.56-7.55 (m, 2H), 7.47 (t, J=8.2 Hz, 1H), 7.33 (d, J=7.6 Hz, 4H), 6.85-6.81 (m, 2H), 6.37 (s, 1H), 2.72-2.70 (m, 4H), 2.13 (s, 3H). HRMS (m/z): [M+H]+ calcd for : 493.5187, found: 493.4924.
Example 2
Preparation of fluorescence detection reagent mother liquor and hydrazine hydrate mother liquor
The fluorescent probe compound prepared in example 1 was carefully transferred to a 50 mL volumetric flask and CH was added at room temperature3CN, fully shaking up to completely dissolve the CN, and finally fixing the volume to a scale mark to obtain 1 mM of fluorescence detection reagent mother liquor. In the testing process, 20 μ L of the above solution is measured by a microsyringe each time, and is dissolved in the testing system, and the total volume of the solution is ensured to be 2 mL each time, at this time, the concentration of the fluorescence detection reagent in the testing system is 10 μ M. Hydrazine hydrate was prepared in 5 mL stock solutions in different concentration gradients (0.1 mM, 0.2 mM, 0.4 mM, 0.7 mM, 1.0 mM, 1.5 mM, 2.0 mM, 3.0 mM, 4.0 mM, 5.0 mM) in PBS buffer. The rest of the tests required the use of small molecules and inorganic salts were separately prepared in PBS buffer solution to a 3 mM concentration of stock solution.
Example 3
Change of fluorescence intensity and hydrazine hydrate concentration of fluorescence detection reagent
50. mu.L of a mother solution of a fluorescence detection reagent having a concentration of 1 mM is dissolved in a mixed solution of 3450. mu.L and 1450. mu.L each of a PBS buffer solution and an acetonitrile solution, and then 50. mu.L of mother solutions of hydrazine hydrate having different concentrations are transferred to the system so that the concentration of the probe in the whole detection system is 10. mu.M and the concentrations of hydrazine hydrate are 1. mu.M, 2. mu.M, 4. mu.M, 7. mu.M, 10. mu.M, 15. mu.M, 20. mu.M, 30. mu.M, 40. mu.M and 50. mu.M, respectively. After incubation for 20 min at room temperature with sufficient response, the fluorescence spectra of the different systems were tested in 10 mm cuvettes. The fluorescence emission spectrum change is shown in figure 1. The result shows that the fluorescence intensity of the system at 682 nm is gradually enhanced along with the increase of the concentration of the hydrazine hydrate. FIG. 2 is a linear graph of the change of fluorescence intensity of the fluorescence detection reagent prepared in example 1 with respect to the concentration of hydrazine hydrate, and it can be seen from FIG. 2 that the fluorescence detection reagent exhibits a good linear relationship in the range of 0-7 μ M, the linear equation is y =22.41343x +26.421, and the linear correlation coefficient is: 0.99454, and the limit of detection (LOD) was calculated to be 0.32. mu.M (S/N-3), indicating that the fluorescence detection reagent has good sensitivity.
Example 4
Fluorescence spectrum of fluorescence detection reagent reacted with different substances
Dissolving 50 μ L of 1 mM fluorescence detection reagent mother liquor in mixed solution of 3450 μ L and 1450 μ L of PBS buffer solution and acetonitrile solution, transferring 50 μ L of 2 mM hydrazine hydrate mother liquor and 3 mM NaClO, NaCN, and NaHSO3、Na2S、Na2SO4、NaBr、ZnCl2And respectively adding NaI mother liquor into the detection system to ensure that the concentration of a probe of the whole detection system is 10 mu M and the concentration of hydrazine hydrate is 20 mu M, and NaClO, NaCN and NaHSO are added3、Na2S、Na2SO4、NaBr、ZnCl2The concentration of NaI was 30. mu.M. After incubation for 20 min at room temperature and full response, fluorescence spectra of different systems are tested in a cuvette with the thickness of 10 mm, the relative fluorescence intensity value at 682 nm is calculated, the corresponding fluorescence intensity at 682 nm is taken as the ordinate, and a response histogram of the probe to different substances is obtained, and the result is shown in fig. 3. The results show that only hydrazine hydrate has higher responsiveness to the detection reagent.
Example 5
Adding 10 μ M of fluorescence detection reagent solution into HeLa culture medium, and placing at 37oC, 5% CO2After incubation in the incubator for 30 minutes, the cells were washed three times with 0.1M PBS buffer (10 mM, pH = 7.4) to remove probe molecules that have not entered the cells, the medium was then replaced, and the cells were incubated with hydrazine hydrate buffer solution (25 μ M) for 30 minutes, washed three times with 0.1M PBS buffer (10 mM, pH = 7.4), and subjected to fluorescence change under a fluorescence microscope, as shown in fig. 4. Experiments show that the probe molecules entering the cell body react with hydrazine hydrate to emit strong red fluorescence, so that the fluorescence detection reagent has good imaging effect on the hydrazine hydrate in the cell and can be used for detecting the hydrazine hydrate in the organism.
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 (3)
1. A novel hydrazine hydrate fluorescence detection reagent is a near-infrared molecular probe and is characterized by having a structure shown in a formula (I):
formula I.
2. The method for preparing a novel fluorescent probe for detecting hydrazine hydrate according to claim 1, wherein the method comprises the following steps:
dissolving o-hydroxybenzaldehyde and DCM-CHO into absolute ethyl alcohol, adding tetrahydropyrrole as a catalyst, placing a reaction system at room temperature, and stirring until the reaction is complete, so that a large amount of red solid is separated out; and (3) carrying out suction filtration, washing with absolute ethyl alcohol for three times, and drying to obtain a compound 1, wherein the structure of the compound 1 is as follows:
dissolving the compound 1 and levulinic acid in anhydrous dichloromethane, and adding EDC and DMAP as a condensing agent and a catalyst; and stirring the reaction system at room temperature until the reaction is finished, removing the solvent under reduced pressure, and purifying by column chromatography to obtain the target molecular probe.
3. Use of the fluorescence detection reagent according to claims 1 and 2, for the detection of hydrazine hydrate in the environment and in cells.
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| CN116496290A (en) * | 2023-03-24 | 2023-07-28 | 湘潭大学 | Preparation and application of hydrazine fluorescence probe based on pyran-coumarin dye |
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2020
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