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Fluorescent probe for detecting hydrogen sulfide by virtue of fluorescence enhancement as well as synthetic method and application of fluorescent probe

A fluorescence-enhanced and fluorescent molecular probe technology is applied in the preparation of fluorescence-enhanced detection of hydrogen sulfide fluorescent probes, and the application field of hydrogen sulfide detection, and can solve the problems of large background interference, slow hydrogen sulfide response speed, and high detection limit. Achieve the effect of high sensitivity, wide detection range and fast response speed

Inactive Publication Date: 2015-03-18
SUZHOU ROWLAND BIOTECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Most of the reported fluorescent probes respond to hydrogen sulfide only in the visible light region, and the background interference is relatively large. At the same time, the response speed to hydrogen sulfide is slow and the detection limit is high.

Method used

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  • Fluorescent probe for detecting hydrogen sulfide by virtue of fluorescence enhancement as well as synthetic method and application of fluorescent probe
  • Fluorescent probe for detecting hydrogen sulfide by virtue of fluorescence enhancement as well as synthetic method and application of fluorescent probe
  • Fluorescent probe for detecting hydrogen sulfide by virtue of fluorescence enhancement as well as synthetic method and application of fluorescent probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the preparation of compound 3

[0034] In a 100 mL single-necked flask, add 4-dimethylaminocinnamaldehyde (0.35 g, 2 mmol), o-hydroxyacetophenone (0.27 g. 2 mmol) and sodium hydroxide (0.2 g, 5 mmol) dissolved in 20 ml In methanol, the temperature was raised to reflux for 5 hours. After the reaction was completed, cool to room temperature, pour the reaction solution into ice water, adjust the pH value to about 2 with hydrochloric acid, and precipitate a large amount of solids. The solid was collected by suction filtration, dried, and recrystallized from ethanol. The solid product 0.38 g (yield: 65 %) was obtained as compound 2.

[0035] δ H (400 MHz, CDCl 3 ): δ 7.83 (dd, J = 8.1, 1.3 Hz, 1H), 7.74 (dd, J = 14.5, 11.2 Hz, 1H), 7.48 – 7.39 (m, 3H), 7.11 (d, J = 14.5 Hz, 1H), 7.04 – 6.97 (m, 2H), 6.94 – 6.83 (m, 2H), 6.70 (d, J = 7.7 Hz, 2H), 3.03 (s, 6H).

[0036]

Embodiment 2

[0037] Embodiment 2: the preparation of compound 2

[0038] Under ice cooling, compound 3 (293 mg, 1 mmol) and 2 mL of 20% sodium hydroxide solution were dissolved in 20 mL of methanol solution, and 1 mL of 30% hydrogen peroxide was added dropwise to the reaction solution. After the dropwise addition, the temperature was raised to reflux for 3 hours. After the reaction was completed, the temperature was lowered to room temperature, and a precipitate was precipitated. Collect the precipitate and dry the obtained product as compound 2. 175 mg (yield: 57 %)

[0039] 1 H NMR (400 MHz, DMSO- d 6 ) δ 7.95 (d, J = 8.4 Hz, 1H), 7.43 (dd, J = 17.0, 9.1 Hz, 3H), 7.34 (d, J = 8.8 Hz, 2H), 7.17 (ddd, J = 7.9, 5.0, 2.9 Hz, 1H), 6.97 (d, J = 16.2 Hz, 1H), 6.66 (d, J = 8.8 Hz, 2H), 2.88 (s, 6H).

[0040]

Embodiment 3

[0041] Embodiment 3: the preparation of fluorescent probe

[0042] Compound 2 (31 mg, 0.1 mmol), 2,4-dinitrofluorobenzene (22 mg, 0.12 mmol) and potassium carbonate (17 mg, 0.12 mmol) were dissolved in 10 ml of acetonitrile and refluxed for 8 hours. Cool down, pour into water, extract with dichloromethane, dry over anhydrous sodium sulfate, and separate by column chromatography (dichloromethane) to obtain 36 mg of the product (yield: 76 %), which is the probe compound.

[0043] 1 H NMR (400 MHz, DMSO- d 6 ) δ 9.33 (d, J = 2.7 Hz, 1H), 8.76 (dd, J = 9.3, 2.8 Hz, 1H), 8.45 (d, J = 7.9 Hz, 1H), 8.35 – 8.16 (m, 3H), 8.01 (d, J = 8.8 Hz, 2H), 7.93 (t, J = 8.8 Hz, 2H), 7.41 (d, J = 15.9 Hz, 1H), 7.16 (d, J = 8.8 Hz, 2H), 2.92 (s, 6H).

[0044]

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Abstract

The invention relates to a fluorescence enhancement type hydrogen sulfide fluorescent probe and particularly relates to a fluorescence enhancement type hydrogen sulfide fluorescent probe based on flavone derivatives. Flavone derivatives are directly reacted with 2,4-dinitrofluorobenzene, and a reaction product is subjected to column chromatography to generate a pure probe product. According to the fluorescence enhancement type hydrogen sulfide fluorescent probe, probe molecules have the maximum absorption wavelengths of 460nm, relatively good solubility in a 1.5mM CTAB water solution and stable optical performance; by adding the probe molecules together with hydrogen sulfide, the absorption wavelengths are blueshifted from 460nm to 450nm, and the intensity of a fluorescence spectrum is continuously enhanced at 612nm and is maximally enhanced by 96 times. According to the fluorescence enhancement type hydrogen sulfide fluorescent probe, the deficiencies that an existing fluorescent probe is slow in response to hydrogen sulfide and high in detection line, and detection wavelengths are in a visible light region are overcome; the probe molecules are high in sensitivity, stable in optical performance, relatively high in synthetic yield, strong in capability of identifying hydrogen sulfide, high in response speed, wide in detection range and low in detection lower limit, the response range is 0-50 mu M, and the detection limit is 0.09 mu M; therefore, the fluorescent probe has practical application values in the fields of biological chemistry, environmental science and the like.

Description

technical field [0001] The invention relates to the technical field of chemical analysis and detection, in particular to a preparation method of a fluorescent probe for fluorescence enhanced detection of hydrogen sulfide and the application of the fluorescent probe in the detection of hydrogen sulfide. [0002] Background technique [0003] Hydrogen sulfide, known for its unpleasant rotten egg smell, has traditionally been regarded as a poisonous gas. Recent studies have shown that hydrogen sulfide is an endogenous gas signaling compound with biological importance equal to other known endogenous gas signaling molecules carbon monoxide and nitric oxide. Hydrogen sulfide has been identified as a modulator in many biological processes. Studies have shown that as a switch of K-ATP channel, hydrogen sulfide can affect the cardiovascular system. In the treatment of ischemic heart failure, hydrogen sulfide plays a positive protective role by combining its anti-oxidation and anti-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D311/22G01N21/64
Inventor 宋相志陈颂
Owner SUZHOU ROWLAND BIOTECH
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