Method for preparing hydrogen sulphide fast and highly selectively colorimetric probe

A technology of colorimetric probe and hydrogen sulfide, which is applied in the preparation of organic compounds, chemical instruments and methods, and the preparation of carboxylic acid nitriles. Simple, water-soluble effect

Inactive Publication Date: 2013-04-03
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among these numerous detection methods, fluorescent probes have become the focus of researchers due to their unique advantages, but there are still some problems in the reported fluorescent probes, including insufficient selectivity, insufficient response speed, complex synthesis and Water solubility is not good enough
The rapid catabolism of hydrogen sulfide in living organisms causes continuous fluctuations in the content of hydrogen sulfide in living organisms, which brings great difficulties to the detection of hydrogen sulfide in living organisms. Therefore, it is necessary to develop analytical methods that can quickly detect hydrogen sulfide in living organisms of

Method used

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  • Method for preparing hydrogen sulphide fast and highly selectively colorimetric probe
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  • Method for preparing hydrogen sulphide fast and highly selectively colorimetric probe

Examples

Experimental program
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Effect test

Embodiment 1

[0035]

[0036] (Scheme 1) Dissolve 377.3mg (1mmol) of nitrogen-phenyldiethanolamine and 128mg (1.0mmol) of tetracyanoethylene in 20mL of N,N-dimethylformamide (DMF), then heat and reflux at 80°C for 4h, Then use ethyl acetate to extract to get the ethyl acetate phase, and then rotary evaporate to get the crude product, then use the mixed system of dichloromethane and anhydrous methanol (v / v, 100:1) for column chromatography to get the red pure product 298mg, the yield was 59%.

[0037] (Scheme 2) Dissolve 377.3mg (1mmol) of nitrogen-phenyldiethanolamine and 192mg (1.5mmol) of tetracyanoethylene in 20mL of N,N-dimethylformamide (DMF), then heat and reflux at 80°C for 4h, Then use ethyl acetate to extract to get the ethyl acetate phase, and then rotary evaporate to get the crude product, then use the mixed system of dichloromethane and anhydrous methanol (v / v, 100:1) for column chromatography to get the red pure product 415mg, the yield was 82%.

[0038](Scheme 3) Dissolve...

Embodiment 2

[0043] The inventor of the present invention has carried out following test: (a) different concentration Na 2 Effect of S (0-200μM) on the absorption spectrum of the probe (5μM); (b) the relationship between the absorption intensity at 527nm and the added Na 2 The linear relationship between S concentration (0-130μM); (c) different concentrations of Na 2 The color of the probe solution (5 μM) changed from pink to colorless in the presence of S (from left to right: 0, 50, 100, 200, 300, 400, 500 μM). The above determination was carried out in water (20mM PBS, pH 7.4), the probe used was the probe prepared in Example 1, and all spectral tests were carried out at 25°C under Na 2 Measured after adding S for 10 min. See Figure 1 for the results.

[0044] It can be seen from Figure 1 that with the Na in the probe solution 2 With the increase of S concentration, the absorption spectrum decreased gradually, and at 0 - 130 μM Na 2 In the concentration range of S, Na 2 The concen...

Embodiment 3

[0046] The effect of different analytes (150 μM) on the absorption spectrum of the probe (5 μM). Analytes include: cysteine ​​Cys, glutathione GSH, leucine Leu, proline Pro, threonine Thr, glutamic acid Glu, glycine Gly, potassium ion K + , calcium ion Ca 2+ , Zinc ion Zn 2+ , Sulfate ion SO 4 2- , nitrate ion NO 3 - , perchlorate ion ClO 4 - , Sodium Sulfide Na 2 S, their concentration is 150 μM. All test conditions were completed in water (20mM PBS, pH 7.4), the probe used was the probe prepared in Example 1, and all spectra were measured after adding the analyte at 25°C for 10 minutes . Specifically, pipette 25 μL of the probe stock solution (1 mM) into a 5 mL colorimetric tube, then add 3 mL of ultrapure water, then pipette 75 μL of the above analyte stock solution (10 mM) into the colorimetric tube, and then pipette 0.5 mL of PBS solution (pH 7.4, 200mM), and finally dilute to 5mL with ultrapure water. Shake well, let it stand for 10min, then measure. The res...

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Abstract

The invention relates to a method for preparing a hydrogen sulphide fast and highly selectively colorimetric probe and particularly relates to a method for preparing a tri-cyano vinyl nitrogen phenyl compound as a hydrogen sulphide fast and highly selectively colorimetric probe and the application of the colorimetric probe. The probe can be used for identifying the hydrogen sulphide highly selectively and analyzing the hydrogen sulphide qualitatively and quantitatively through the observation of naked eyes. The probe is synthesized easily by adopting the heating method through one-step reaction.

Description

technical field [0001] The invention relates to a preparation method of a fast and highly selective hydrogen sulfide colorimetric probe. Background technique [0002] Hydrogen sulfide is famous for its typical smell of rotten eggs and toxicity. However, recent studies have found that hydrogen sulfide in living bodies has many physiological functions. Hydrogen sulfide has become the third bioactive gas signal molecule discovered after nitric oxide and carbon monoxide. Hydrogen sulfide in the living body participates in many physiological processes, and has physiological functions such as dilating blood vessels, regulating blood pressure, myocardial contraction, regulating the respiratory system, inhibiting cell apoptosis, and neurotransmission. Once the hydrogen sulfide content in the living body cannot be maintained within the normal physiological range, many diseases will occur in the living body, including arterial and pulmonary hypertension, heart disease, Alzheimer's di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/42C07C253/30G01N33/52
Inventor 朱宝存赵允洲
Owner UNIV OF JINAN
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