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Fluorescent probe of recognizing H2S based on 4-styrene pyridinium long wave emission and synthetic method and application thereof

A styrene pyridinium salt, fluorescent probe technology, applied in luminescent materials, fluorescence/phosphorescence, chemical instruments and methods, etc., can solve problems such as complex synthesis routes, photodamage of cells and biological tissues, detection and imaging interference, etc.

Active Publication Date: 2018-12-28
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Anal.Chem., (2018), 90, 7510-7516; Anal.Chem., (2015), 87, 1188-1195; J.Org.Chem., (2017), 82, 10234-10246; Chem.Commun .,(2012),48,10871-10837; Anal.Chem.,(2013),85,7875-7881, although these documents can specifically identify H 2 S, but the emission wavelength is short, it cannot be detected in the long wavelength region, and the synthesis route is complicated and the response time is long
As we all know, in the visible spectral region, biological samples have strong background fluorescence and self-absorption, which will interfere with detection and imaging and affect the accuracy of measurement.
At the same time, the wavelength of visible light is short, and the radiation energy is relatively large during fluorescence imaging, which is easy to cause photodamage to cells and biological tissues.

Method used

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  • Fluorescent probe of recognizing H2S based on 4-styrene pyridinium long wave emission and synthetic method and application thereof
  • Fluorescent probe of recognizing H2S based on 4-styrene pyridinium long wave emission and synthetic method and application thereof
  • Fluorescent probe of recognizing H2S based on 4-styrene pyridinium long wave emission and synthetic method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) The specific synthetic steps of compound 1 are as follows:

[0030]

[0031] 4-Diethylamino salicylaldehyde (1.54g, 8.0mmol), 4-picoline salt (1.88g, 8.0mmol) and piperidine (0.8mmol) were dissolved in ethanol, heated to reflux for 12h, and the solvent was spun off. The crude product was purified by thin-layer column chromatography using CH 3 OH:CH 2 Cl 2 =1:50 (v / v) was used as eluent, and 2.05g of compound 1 was isolated with a yield of 62.5%;

[0032] 1 H NMR (400MHz, DMSO-d 6 )δ10.13(s,1H),8.59(d,J=6.5Hz,2H),8.03-7.93(m,3H),7.49(d,J=9.0Hz,1H),7.15(d,J=16.0 Hz,1H),6.33(dd,J=9.0,2.4Hz,1H),6.21(d,J=2.4Hz,1H),4.15(s,3H),3.39(q,J=7.0Hz,4H), 1.15(t,J=7.0Hz,6H).

[0033] (2) The specific synthesis steps of fluorescent probe L are as follows:

[0034]

[0035] Compound 1 (410mg, 1mmol), 2,4-dinitrofluorobenzene (223mg, 1.2mmol), potassium carbonate (207mg, 1.5mmol), were dissolved in 10mL DMF, and reacted at room temperature for 6h. After the reaction, wash...

Embodiment 2

[0039] (1) Synthesis of Compound 1

[0040] 4-Diethylamino salicylaldehyde (1.54g, 8.0mmol), 4-picoline salt (3.76g, 16.0mmol) and piperidine 16mmol were dissolved in ethanol, heated to reflux for 8h, and the solvent was spun off. The crude product was purified by thin-layer column chromatography using CH 3 OH:CH 2 Cl 2 =1:100 (v / v) was used as the eluent, and compound 1 was obtained by separation;

[0041] (2) Synthesis of fluorescent probe L

[0042] Compound 1 (410mg, 1.0mmol), 2,4-dinitrofluorobenzene (278.5mg, 1.5mmol), potassium carbonate (276mg, 2.0mmol) were dissolved in 15mL DMF, and reacted at room temperature for 8h. After the reaction, wash with water, extract with ethyl acetate, dry over anhydrous sodium sulfate, spin out the solvent, and purify the crude product by thin-layer column chromatography, using CH 3 OH:CH 2 Cl 2 =1:80 (v / v) was used as the eluent to obtain 420 mg of probe L with a yield of 72.9%. fluorescent probe L 1 H NMR spectrum as figure ...

Embodiment 3

[0044] (1) Synthesis of compound 1

[0045] 4-Diethylamino salicylaldehyde (1.54g, 8.0mmol), 4-picoline salt (9.4g, 40.0mmol) and piperidine 8mmol were dissolved in ethanol, heated to reflux for 16h, and the solvent was spun off. The crude product was purified by thin-layer column chromatography using CH 3 OH:CH 2 Cl 2 =1:100 (v / v) was used as the eluent, and compound 1 was obtained by separation;

[0046] (2) Synthesis of fluorescent probe L

[0047] Compound 1 (410mg, 1.0mmol), 2,4-dinitrofluorobenzene (371mg, 2mmol), potassium carbonate (414mg, 3.0mmol) were dissolved in 15mL DMF, and reacted at room temperature for 10h. After the reaction, wash with water, extract with ethyl acetate, dry over anhydrous sodium sulfate, spin out the solvent, and purify the crude product by thin-layer column chromatography, using CH 3 OH:CH 2 Cl 2 =1:100 (v / v) was used as eluent to obtain fluorescent probe L. fluorescent probe L 1 H NMR spectrum as figure 1 as shown, 13 C NMR spect...

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Abstract

The invention relates to a fluorescent probe of recognizing H2S based on 4-styrene pyridinium long wave emission and a synthetic method and application thereof. The fluorescent probe has a structuralformula as follows: a formula is as shown in the description. The preparation method comprises the following steps: inputting 4-(diethylamino) salicylaldehyde, 4-methyl pyridinium and piperidine by taking ethanol as a solvent; heating the mixture for a reflux reaction; spinning out a solvent; purifying a coarse product by means of silica gel column chromatography; carrying out separation by methane and dichloromethane as an eluent to obtain a compound 1; inputting compounds 1,2,4-dinitrofluorobenzene and potassium carbonate by taking DMF as a solvent; stirring the mixture at room temperature;filtering the mixture to obtain a coarse product; purifying the coarse product by means of silica gel column chromatography; and carrying out separation through an eluent to obtain the fluorescent probe L. The fluorescent probe has the advantages that the fluorescent probe is simple in synthetic step and easy to separate and purify; the fluorescent probe can recognize H2S in a water medium in an enhanced manner by long wave emission of fluorescence, has good selectivity, relatively high sensitivity and relatively good interference resistance and can be applied to an actual water sample to detect H2S.

Description

technical field [0001] The invention relates to a method based on 4-styrene pyridinium salt long-wave emission recognition H 2 S fluorescent probes and their synthesis methods and applications. Background technique [0002] Hydrogen sulfide (H 2 S), a newly discovered gaseous signaling molecule, has become a research hotspot in the field of biology due to its diverse functions in physiological and pathological processes. h 2 S mainly comes from volcanic eruptions and mammalian cells themselves through cystathionine-β-synthase (CBS), cystathionine-γ-lyase (CSE), 3-mercaptopyruvate sulfur transferase (3-MST), etc. produced by the action of enzymes. Previous studies have shown that H 2 S plays an important role in regulating blood pressure, cardiovascular protection, regulating cell growth and stimulating angiogenesis. In addition, high levels of H in living systems 2 S can cause human diseases such as Alzheimer's disease, Down's syndrome, hypertension and liver cirrhosi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/38C09K11/06G01N21/64
CPCC07D213/38C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029G01N21/643
Inventor 钟克利汤立军曲秀莉侯淑华任欢欢李秋莹徐永霞边延江周诗怡
Owner BOHAI UNIV
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