Hydrogen sulfide recognition and detection fluorescent probe, preparation method and applications thereof

A fluorescent probe and hydrogen sulfide technology, applied in the field of chemical analysis, can solve the problems of inability to detect hydrogen sulfide, and achieve the effect of fast response and good water solubility

Active Publication Date: 2020-04-28
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional hydrogen sulfide detection techniques such as colorimetry and gas chromatography can detect the production of hydrogen sulfide, but they cannot detect hydrogen sulfide in living cells and tissues with selectivity and sensitivity

Method used

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  • Hydrogen sulfide recognition and detection fluorescent probe, preparation method and applications thereof
  • Hydrogen sulfide recognition and detection fluorescent probe, preparation method and applications thereof
  • Hydrogen sulfide recognition and detection fluorescent probe, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Preparation of compounds of general formula (1):

[0032]

[0033] Follow the steps below:

[0034] 1) Preparation of compound L2-1:

[0035]

[0036] Dissolve DMF (2.1mL, 27.3mmol) in 5mL of dichloromethane, and slowly add phosphorus oxychloride (2.3mL, 25mmol) in dichloromethane solution dropwise at 0°C, compound A (1.65g, 12.4mmol) Dichloromethane solution was added dropwise to the above solution, and refluxed at 45°C for 6h. The reaction was cooled to room temperature, 5M NaOH solution was added under an ice-water bath to adjust the pH to 8, the layers were separated, the organic layer was washed 3 times with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and passed through a neutral alumina column (PE:EA= 8:1), to obtain 1.35 g of bright yellow solid L2-1 with a yield of 53%. LC-MS (ESI) m / z: 207.1 [M] + ;

[0037] 2) Preparation of compound L2-2:

[0038]

[0039] Compound L2-1 (898mg, 5mmol) was dissolved in NaOH in eth...

Embodiment 2

[0056] Example 2 Changes in the ultraviolet absorption spectrum of the probe (1) in response to hydrogen sulfide

[0057] Add 3 mL of PBS (10 mM, pH 7.4) to the quartz cuvette for zero baseline adjustment, then add 10 μL of L2-B acetonitrile stock solution to make the final concentration 10 μM, and then add 5 times the equivalent of NaSH solution to test the difference Changes in UV absorption of time probe L2-B reacting with hydrogen sulfide. Depend on image 3 It can be seen that with the prolongation of time, the absorption peak of the probe at 555nm gradually decreases, while the ultraviolet absorption at 470nm gradually increases, reaching the peak at 15min.

Embodiment 3

[0058] Example 3 Fluorescence Spectrum Change of Probe (1) Responding to Hydrogen Sulfide

[0059] Add 3mL of PBS (10mM, pH7.4) to the quartz cuvette, then add 10μL of L2-B acetonitrile stock solution to make the final concentration of 10μM, then add 2.5 times the equivalent of NaSH solution, detect probe L2-B and Fluorescence-time variation of the hydrogen sulfide response. Depend on Figure 4 It can be seen that as the reaction time prolongs, the fluorescence of the probe at 576nm is gradually quenched, and a new peak appears at 542nm, and the reaction reaches equilibrium in 15min.

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PUM

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Abstract

The invention belongs to the technical field of chemical analysis, and relates to a small molecular fluorescent probe, particularly to a hydrogen sulfide fluorescent probe with a structure representedby a formula (1), a preparation method and applications thereof, wherein the probe belongs to a BODIPY structure fluorescent probe, has good stability and good water solubility, and can be used for quickly and sensitively detecting hydrogen sulfide.

Description

Technical field: [0001] The invention belongs to the technical field of chemical analysis, and relates to a small molecule fluorescent probe, in particular to a hydrogen sulfide fluorescent probe and its preparation method and application. It has good stability and water solubility, and can quickly and sensitively detect hydrogen sulfide. [0002] technical background: [0003] The prior art discloses that hydrogen sulfide is another gas signal molecule after nitric oxide, and it is the simplest biothiol, which can be produced in the human body through enzymatic or non-enzymatic pathways. Studies have shown that hydrogen sulfide and other reactive sulfur species play an important role in a series of physiological reactions that maintain the healthy state of cells. Studies have shown that abnormal levels of hydrogen sulfide may contribute to a variety of diseases, such as diabetes, Parkinson's disease and Alzheimer's disease. Although more and more studies have found that hy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06G01N21/643C09K2211/1029C09K2211/1055G01N2021/6432
Inventor 古险峰李咪咪陈纪安
Owner FUDAN UNIV
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