Fluorescence chemical sensor capable of selectively detecting biological sulfhydryl compound, preparation method and application of fluorescence chemical sensor

A technology of chemical sensors and mercapto compounds, which is applied in the field of chemical sensors, can solve the problem of fewer molecules in the sensor, and achieve the effects of high sensitivity, easy control of reaction conditions, and high molecular yield of products

Inactive Publication Date: 2013-04-03
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, some reactive thiol sensors have been reported one after another, but due to the similarity in structure and properties of thiol-containing compounds, sensors that can distinguish cysteine ​​from homocysteine ​​and glutathione very few molecules

Method used

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  • Fluorescence chemical sensor capable of selectively detecting biological sulfhydryl compound, preparation method and application of fluorescence chemical sensor
  • Fluorescence chemical sensor capable of selectively detecting biological sulfhydryl compound, preparation method and application of fluorescence chemical sensor
  • Fluorescence chemical sensor capable of selectively detecting biological sulfhydryl compound, preparation method and application of fluorescence chemical sensor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] A preparation method and application of a fluorescent chemical sensor capable of selectively detecting biothiol compounds:

[0049] (1) Synthesis of BODIPY main compound:

[0050]①Weigh 8g (66.6mmol) of p-tolualdehyde, add 100mL (1441mmol) of pyrrole, slowly drop 0.5mL (6.7mmol) of trifluoroacetic acid into it during stirring, stir at room temperature for 10 minutes, and distill off pyrrole under reduced pressure A black viscous liquid was obtained, and the residue was subjected to column chromatography to obtain the compound represented by formula (B):

[0051]

[0052] ②Dissolve 2g (8.5mmol) of the compound shown in formula B in 100mL tetrahydrofuran, pass N 2 , cooled to -78°C, added 2.3g (17.2mmol) N-chlorosuccinimide, stirred at -78°C for 2 hours, then placed in the refrigerator for 18 hours, evaporated the solvent, and the residue Diluted with 100 mL of dichloromethane, washed 3 times with distilled water, dried the organic layer with anhydrous magnesium sulf...

Embodiment 2

[0072] A preparation method of a fluorescent chemical sensor for selectively detecting biological thiol compounds:

[0073] (1) Synthesis of BODIPY main compound: same as Example 1;

[0074] (2) Weigh 100mg (0.18mmol) of BODIPY main compound A and dissolve it in acetonitrile, pass through N 2 , add 125 mg (0.9 mmol) p-nitrophenol and 250 μL (1.8 mmol) triethylamine, N 2 Reflux for 5 hours under protection. The solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography to obtain the fluorescent compound shown in formula (II).

[0075] Light sensor molecules:

[0076]

[0077] Prepare 1 mmol / L acetonitrile solution of the compound represented by formula (II).

[0078] Cys absorption and emission spectrum test of the compound shown in formula (I): Use acetonitrile / HEPES buffer solution (v / v=2 / 8, 20mM, pH=7.4) to prepare 1mmol / L Cys, GSH and Hcy solutions and blank solution. Take 2 mL of the above-mentioned different solutions...

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Abstract

The invention relates to a fluorescence chemical sensor capable of selectively detecting a biological sulfhydryl compound, which is characterized by comprising the structural formula shown in the description, wherein, in the formula, R is one of the following structures shown in the description. The fluorescence chemical sensor, provided by the invention, has the advantages that the used raw materials are easily obtained, a synthetic method is simple, reaction conditions are easy to control, the sensitivity is high, the sub yield of the molecular weight of a product is high, a sulfhydryl-containing compound can be selectively recognized, and cysteine, glutathione and homocysteine can be separated from each other.

Description

technical field [0001] The invention relates to a fluorescent chemical sensor capable of selectively detecting biological mercapto compounds, a preparation method and an application thereof, and belongs to the technical field of chemical sensors. Background technique [0002] Sulfhydryl-containing biomolecules, such as cysteine ​​(Cys), homocysteine ​​(Hcy), and glutathione (GSH), play an important role in maintaining the stability of biological systems. Cysteine ​​is involved in biological proteases and oxidation-reduction reactions in the body, and its deficiency can lead to diseases such as neurotoxicity, liver damage, hair discoloration, edema, etc.; as an intermediate product of methionine metabolism, homocysteine ​​is the cause of An important factor of sclerosis, the high content of homocysteine ​​in plasma may lead to a series of diseases such as neural tube defects, osteoporosis, Alzheimer's disease, cardiovascular disease; glutathione as an intracellular content T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F5/02G01N21/76
Inventor 陈玉哲牛丽亚杨清正吴骊珠佟振合
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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