Fluorescent probe for detecting biological hydrogen sulfide as well as preparation and application of fluorescent probe

A fluorescent probe, hydrogen sulfide technology, used in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve the problems of not being able to measure hydrogen sulfide in cells, large detection errors, etc., to achieve good biofilm permeability, avoid Interference, good effect of biofilm permeability

Inactive Publication Date: 2013-06-26
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the detection errors of these two methods are relatively large, and they can only measure hydrogen sulfi

Method used

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  • Fluorescent probe for detecting biological hydrogen sulfide as well as preparation and application of fluorescent probe
  • Fluorescent probe for detecting biological hydrogen sulfide as well as preparation and application of fluorescent probe
  • Fluorescent probe for detecting biological hydrogen sulfide as well as preparation and application of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: the preparation of fluorescent probe

[0020] The reaction formula is as follows:

[0021] .

[0022] The preparation steps are as follows:

[0023] (1) Preparation of formula II: appropriate amount of (E)-3-(2-((tert-butyldimethylsilyloxy)methyl)-5-formyl)phenyl-methyl acrylate (0.18-0.25 g ) and 1,3-dimethylfluoroborate dipyrrole fluorophore (0.10-0.15g) were dissolved in benzene (or toluene), added 0.1ml acetic acid and 0.1ml piperidine, heated to reflux for 4-5 hours, and divided The water tank removes the water generated by the reaction. After the reaction was completed, it was cooled to room temperature and quenched by adding water. The crude product was extracted with ethyl acetate, spin-dried, and purified by silica gel column chromatography.

[0024] (2) Preparation of formula III: the compound represented by formula II (0.10 g-0.20 g) was dissolved in acetonitrile, and 40% hydrofluoric acid aqueous solution (0.02-0.04 mL) was added dropwise...

Embodiment 2

[0027] Example 2: Fluorescence changes before and after the reaction of probe molecules with hydrogen sulfide

[0028] Dissolve the probe molecule in a small amount of acetonitrile, add phosphate buffer solution or sodium hydrogensulfide phosphate buffer solution respectively, so that the final concentration of the probe molecule is 10 μM, and the final concentration of sodium hydrogensulfide is 100 μM. After 1 hour of reaction Measured on a fluorescence spectrometer, and then confirmed that the fluorescence intensity of the probe molecule was significantly enhanced after the reaction with hydrogen sulfide, such as figure 2 shown.

Embodiment 3

[0029] Embodiment 3: the selectivity of probe molecule to hydrogen sulfide

[0030] Dissolve the probe molecules with a small amount of acetonitrile, and then make a solution with phosphate buffer. The samples to be tested dissolved in phosphate buffer were added respectively so that the concentration of the final probe molecule was 10 μM and the concentration of the sample to be tested was 100 μM. After reacting for 1.0 hour, it was measured on a fluorescence spectrometer, and then the selectivity of the probe molecule to hydrogen sulfide was determined. Such as image 3 As shown, the probe molecule has high selectivity to hydrogen sulfide.

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PUM

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Abstract

The invention provides a fluorescent probe for detecting biological hydrogen sulfide, with a structure as shown in a formula (I). The fluorescent probe, though not fluorescing by self in a physiological environment, can specifically and rapidly react with the hydrogen sulfide to generate a product with strong fluorescence, thereby achieving specific detection on the hydrogen sulfide. The fluorescent probe is good in stability and can be preserved for long time to use; the fluorescent probe has a long fluorescence excitation wavelength (>500nm), thereby causing no damage to an organism and being capable of effectively avoiding interference from biological macromolecule background fluorescence; and the fluorescent probe is high in detection signal-to-noise ratio, good in sensitivity, excellent in selectivity, capable of specifically detecting the hydrogen sulfide in a complicated biological sample, and good in biological membrane permeability, so that the fluorescent probe can be used for detecting the hydrogen sulfide in living cells.

Description

technical field [0001] The invention belongs to the field of biological detection, and relates to a fluorescent probe for detecting biological hydrogen sulfide, a preparation method and application thereof. Background technique [0002] Hydrogen sulfide, a colorless, flammable gas with the smell of rotten eggs, has long been considered a poison. However, recent studies have shown that mammals can synthesize a small amount of hydrogen sulfide from homocysteine ​​or cysteine ​​under the catalysis of hydrogen sulfide synthase, and use it as a signal molecule to regulate vasodilation, inflammatory response, Physiological processes such as glucose metabolism. Hydrogen sulfide is the third gas messenger discovered after nitric oxide and carbon monoxide. It can dilate blood vessels by opening ATP-sensitive potassium ion channels in vascular smooth muscle, thereby achieving the effect of lowering blood pressure. Hydrogen sulfide also has cardiovascular protective effects such as ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F5/02G01N21/64
Inventor 李新胡永洲张帅
Owner ZHEJIANG UNIV
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