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A fluorescent probe compound for detecting cysteine ​​and its application

A technology of fluorescent probes and cysteine, which is applied in the direction of fluorescence/phosphorescence, organic chemistry, luminescent materials, etc. It can solve the problems that the detection signal is interfered by the detection background, cannot distinguish Cys, and the yield is low.

Active Publication Date: 2021-09-24
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis method of the above-mentioned probes is complex, the yield is low, time-consuming and labor-intensive
Moreover, the excitation and emission wavelengths of such fluorescent probes are short, and the detection signal is seriously interfered by the detection background.
Cannot distinguish thiols such as Cys and Hcy, which has great application limitations in the accurate detection of Cys in the environment, cells and living bodies

Method used

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  • A fluorescent probe compound for detecting cysteine ​​and its application
  • A fluorescent probe compound for detecting cysteine ​​and its application
  • A fluorescent probe compound for detecting cysteine ​​and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Formula I compound (synthesis of probe BCy-AC) synthetic route diagram is as follows:

[0022]

[0023] Add 1,1,2-trimethyl-1H-benzo[e]indole (105.0mg, 0.5mmol) and iodoethane (78.0mg, 0.5mmol) to 10ml of acetonitrile, and heat the mixture under reflux for 12 hours After filtration, the obtained solid matter and 4-hydroxyisobenzaldehyde (30.0 mg, 0.2 mmol) were heated to reflux in a mixed solvent of n-butanol and toluene (7:3, v / v) for 3 hours to obtain a green crude product ( Compound shown in formula II). The obtained crude product was separated and purified on a silica gel chromatography column (200-300 mesh) with ethyl acetate / methanol (3:1, v / v) as eluent, and the yield was 79%.

[0024] Take a 250mL round-bottomed flask, add 10mL of dichloromethane into it, then add acryloyl chloride (0.16mL, 2mmol) and a small amount of N,N-diisopropylethylamine, and stir at 0°C for 30 minutes under the protection of argon. 10 mL of dichloromethane and formula II (177 mg, 0....

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Abstract

The invention relates to a fluorescent probe compound for detecting cysteine ​​and its application. The compound is represented by formula I. The present invention uses the compound as a fluorescent probe for detecting Cys, and provides a fluorescent probe that can be used for the selective detection of Cys in the environment, in cells and in vivo, and the fluorescence intensity of the fluorescent probe is significantly increased in the presence of Cys, It can be used for the detection of Cys, and can greatly reduce the interference of external detection conditions, and improve the detection speed and accuracy. The probe can be used to deeply study the dynamic mechanism of Cys production, transport and accumulation in the environment and in vivo, and it can also help to clarify the biological role of cysteine ​​in physiological and pathological processes. A new mechanism of acid homeostasis.

Description

technical field [0001] The invention relates to a fluorescent probe compound for detecting cysteine ​​and its application. Background technique [0002] As an important biological sulfhydryl group, cysteine ​​(cysteine, Cys) plays an important role in various physiological processes of biological organisms. Normal Cys concentrations are maintained at micromolar levels, and abnormal levels of intracellular cysteine ​​can lead to many diseases. Abnormal increase of Cys concentration can lead to diseases such as cardiovascular disease, neurotoxicity, Alzheimer's disease and Parkinson's disease, while its deficiency can cause edema, hair loss and liver damage and so on. Most Cys in cells are involved in the synthesis and metabolism of biothiols such as glutathione (GSH) and other biomolecules. In addition, since Cys has similar chemical structure and properties with GSH and homocysteine ​​(Hcy), the detection of Cys is always interfered by GSH and Hcy. A detailed understandin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/60C09K11/06G01N21/64A61K49/00
CPCA61K49/0021C07D209/60C09K11/06C09K2211/1029G01N21/6428G01N21/6456G01N21/6486G01N2021/6432
Inventor 陈令新张霞张良伟韩潇玥高敏
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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