A water-soluble ratiometric fluorescent probe for detecting hydrazine hydrate

A technology of fluorescent probes and hydrazine hydrate, which is applied in the direction of fluorescence/phosphorescence, luminescent materials, measuring devices, etc., can solve the problems of no mention of selectivity, single fluorescence response mode, and difficulty in realizing pure water phase detection, so as to reduce organic The effect of solvent participation, good fluorescence and UV selectivity, and good biological application prospects

Active Publication Date: 2021-06-22
HUAZHONG AGRI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although some fluorescent probes for the detection of hydrazine hydrate have been reported, there are still some shortcomings: 1. The detection process requires a large amount of organic solvents to participate, and it is difficult to achieve pure aqueous phase detection; 2. The fluorescence response mode is single, mainly Fluorescence enhancement or quenching type, it is difficult to eliminate background interference in vivo; 3. Some probes lack selectivity and it is difficult to distinguish hydrazine hydrate from other organic amines
[0004] CN 108003173 A discloses a fluorescent probe, which uses coumarin as a fluorescent matrix and acetate as a recognition group to specifically recognize hydrazine hydrate, but the fluorescent emission peak of the probe itself is at 500nm. After combining with hydrazine hydrate, the fluorescence wavelength blue-shifts to 425nm, which is located in the blue light region, and there is no mention of imaging of living organisms such as zebrafish and detection of hydrazine vapor
In addition, the patent does not mention the selectivity of the compound to other organic amine compounds

Method used

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  • A water-soluble ratiometric fluorescent probe for detecting hydrazine hydrate
  • A water-soluble ratiometric fluorescent probe for detecting hydrazine hydrate
  • A water-soluble ratiometric fluorescent probe for detecting hydrazine hydrate

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Experimental program
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Effect test

Embodiment 1

[0027] Synthesis and structural characterization of embodiment 1 probe

[0028] The substituted o-hydroxybenzaldehyde is used as the starting material, and the target product is finally obtained through cyclization reaction, decarboxylation reaction, Wilsmeyer-Hacker reaction and condensation reaction.

[0029] The synthetic probe route of the probe is as follows:

[0030]

[0031] Synthetic steps:

[0032] (1) References for the preparation of compounds 1, 2, and 3 (Chem. Commun. 2016, 52, 8675-8678).

[0033] (2) Preparation of Compound 4: Dissolve Compound 3 (6mmol, 1.48g) and 4-pyridineacetonitrile (7mmol, 0.83g) in 20mL of absolute ethanol, then add 10 drops of piperidine; the reaction system was stirred at 60°C After 6 hours, the heating was stopped, and it was naturally cooled to room temperature. The precipitated solid was filtered under reduced pressure and dried to obtain 1.43 g of compound 4 as a brown solid, with a yield of 68%. Due to the poor solubility of...

Embodiment 2

[0041] The impact of embodiment 2 probes on the ultraviolet absorption of hydrazine hydrate

[0042] 1. If figure 1 Shown, in 10mM, the PBS buffer solution that pH is 7.4, the ultraviolet absorption of probe (10μM) itself is at 560nm place, after adding 100μM (10 equivalents) hydrazine hydrate, the ultraviolet absorption peak that is positioned at 560nm place obviously reduces, and the new absorption A peak is generated at 450nm. Other types of amines (including methylamine, ammonia, morpholine, N,N-diisopropylethylamine, and aniline) and metal ions (zinc, mercury, and cadmium ions) do not produce UV responses.

[0043] 2. If figure 2 As shown, as the concentration of hydrazine hydrate increases (0-100 μM), the ultraviolet absorption peak at 560 nm gradually decreases, and the ultraviolet absorption peak at 450 nm gradually increases.

[0044] 3. If image 3 As shown, the probe has an excitation wavelength of hydrazine hydrate at 560nm, and the fluorescence emission wavel...

Embodiment 3

[0052] Embodiment 3 probe is to the detection of hydrazine vapor

[0053] Soak 20μL of the probe (1mM) solution in a round filter paper, put it in a fume hood to dry naturally, and put it into a 10mL sample bottle cap, which contains air, water, 0.1%, 1% and 5% respectively hydrazine hydrate solution with a concentration of 1mL, put the lid on and let stand for 20min. Such as Figure 8 As shown, the test paper in contact with air and water vapor has no color change and fluorescence response. After contacting with hydrazine vapor, the color of the test paper gradually changes from dark red to yellow with the increase of the solubility of hydrazine vapor. Under the light, the fluorescence gradually changes to green light.

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Abstract

The invention discloses a water-soluble ratiometric fluorescent probe for detecting hydrazine hydrate, which has the chemical structure shown below. The probe has good fluorescence and ultraviolet selectivity for hydrazine hydrate, and can realize pure water phase It is detected in medium and has good biological application prospects, and can realize ratiometric fluorescence imaging in cells and zebrafish in vivo.

Description

technical field [0001] The invention relates to a water-soluble ratio fluorescent probe for detecting hydrazine hydrate. Background technique [0002] Hydrazine hydrate is an important chemical raw material, commonly used in the preparation of pesticides and pharmaceutical intermediates in industry. However, hydrazine hydrate is highly toxic, and its vapor can irritate the nose and upper respiratory tract, causing dizziness and central nervous system damage. Long-term skin contact with hydrazine hydrate will cause poisoning through skin absorption, and water pollution caused by hydrazine hydrate will also enter the body of fish and possibly lead to its death. Therefore, the detection of hydrazine hydrate is very important for environmental pollution monitoring. [0003] Traditional methods for detecting hydrazine hydrate mainly include mass spectrometry, electrochemical methods, and electrophoresis methods. Compared with the above methods, fluorescent probes have the advan...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/06C09K11/06G01N21/64G01N21/78
CPCC07D405/06C09K11/06C09K2211/1029C09K2211/1088G01N21/6458G01N21/6486G01N21/78
Inventor 李俊位灯国崔元超
Owner HUAZHONG AGRI UNIV
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