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Quick high-selectivity hydrogen sulfide colorimetric probe

A compound and hydrogen atom technology, applied in the field of hydrogen sulfide colorimetric probes, can solve the problems of insufficient selectivity, complex synthesis, difficult hydrogen sulfide detection, etc., and achieve the effects of good water solubility and simple synthesis

Inactive Publication Date: 2013-03-27
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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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041]

[0042] (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%.

[0043] (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%.

[0044] (Scheme 3) Dissolv...

Embodiment 2

[0049] 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.

[0050] 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 gradually decreased, and in the 0-130μM Na 2 In the concentration range of S, Na 2 The concen...

Embodiment 3

[0052] 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 quick high-selectivity hydrogen sulfide colorimetric probe. Specifically, the probe provided by the invention is a tricyanovinyl nitrogen phenyl compound and can be used as a hydrogen sulfide colorimetric probe for detecting hydrogen sulfide. The probe can realize at least one of the following technical effects: identification of hydrogen sulfide / sodium sulfide with high selectivity; qualitative and quantitative analysis of hydrogen sulfide / sodium sulfide in a naked eye observation mode; quick response to hydrogen sulfide; immediate detection on hydrogen sulfide; stable property and long-term storage; good water solubility favorable for detecting hydrogen sulfide under physiological level conditions; and relatively strong anti-jamming capability.

Description

technical field [0001] The present invention relates to tricyanoethylene nitrogen phenyl compounds as hydrogen sulfide colorimetric probes, which can be used in rapid and highly selective identification of hydrogen sulfide under physiological level conditions, or can be used to determine the concentration of hydrogen sulfide / sodium sulfide in samples concentration. 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. On...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/42C07C253/30G01N21/78
Inventor 朱宝存赵允洲
Owner UNIV OF JINAN
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