Fluorescent probe for near infrared detection of cysteine as well as preparation method and application of fluorescent probe

A near-infrared detection and fluorescent probe technology, applied in the field of chemical analysis and detection, can solve the problems of biological imaging application limitations, inability to effectively distinguish cysteine ​​and homocysteine, etc., and achieve high sensitivity and sample penetration Strong, selective effect

Active Publication Date: 2018-06-08
湖南汇百益新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, most of the probes for cysteine ​​(Cys) detection are concentrated in the visible light region or rely on low-sensitivity ultraviolet-visible absorption method detection, and even cannot effectively distinguish cysteine ​​and homocysteine ​​(such as Chinese patent CN105693600A, CN105820810A, CN104447421A, Anal.Chem., 2016, 88(14), pp 7...

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  • Fluorescent probe for near infrared detection of cysteine as well as preparation method and application of fluorescent probe
  • Fluorescent probe for near infrared detection of cysteine as well as preparation method and application of fluorescent probe
  • Fluorescent probe for near infrared detection of cysteine as well as preparation method and application of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] A preparation method of a fluorescent probe, the preparation method comprising the following steps:

[0043]

[0044] The specific experimental operation is as follows:

[0045] Synthesis of 4-piperazine-1-benzaldehyde:

[0046] Add 15g (174.14mmol) of piperazine to a 100mL two-necked round-bottom flask, then add 18mL of water and 25mL of ethylene glycol methyl ether; measure 5mL (46.61mmol) of p-fluorobenzaldehyde with a graduated cylinder, and then add it to a constant pressure dropping funnel , add 5mL of ethylene glycol methyl ether to mix with it, and slowly drop it into the above-mentioned reaction flask under stirring; after the dropwise addition at room temperature, heat and reflux for 4 hours; wait for the reaction solution to cool to room temperature, pour the reaction solution into 200mL of water, and filter. Add the filter cake to 150mL of 10% hydrochloric acid solution and stir for 10 minutes, filter to remove insoluble matter, adjust the pH of the solu...

Embodiment 2

[0052] The processes of this embodiment and Embodiment 1 are basically the same, where the differences are:

[0053] The molar ratio of piperazine to p-fluorobenzaldehyde is 3:1 (139.83mmol:46.61mmol);

[0054] The molar ratio of 4-piperazine-1-benzaldehyde and 2-(3,5,5-trimethylcyclohex-2-enylidene) malononitrile is 1:1.05 (2.63mmol:2.76mmol);

[0055] The molar ratio of 2-(3,5,5-trimethylcyclohex-2-enylidene)malononitrile to 2,4-dinitrobenzenesulfonyl chloride was 1:1.05 (1 mmol:1.05 mmol).

[0056] In this example, the final result is the same as the experimental product in Example 1, indicating that the fluorescent probe can also be successfully synthesized under the above-mentioned ratio.

Embodiment 3

[0058] The processes of this embodiment and the embodiment are basically the same, where the differences are:

[0059] The molar ratio of piperazine to p-fluorobenzaldehyde is 4:1 (186.44mmol: 46.61mmol);

[0060] The molar ratio of 4-piperazine-1-benzaldehyde and 2-(3,5,5-trimethylcyclohex-2-enylidene) malononitrile is 1:1 (2.63mmol: 2.63mmol);

[0061] The molar ratio of 2-(3,5,5-trimethylcyclohex-2-enylidene)malononitrile and 2,4-dinitrobenzenesulfonyl chloride was 1:1.05 (1 mmol: 1 mmol).

[0062] In this example, the final result is the same as the experimental product in Example 1, indicating that the fluorescent probe can also be successfully synthesized under the above-mentioned ratio.

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Abstract

The invention provides a fluorescent probe with the advantages of reduced background interference, high sample penetration performance, good selectivity, high sensitivity and good imaging resolution for fluorescence open-close type near infrared detection of cysteine as well as a preparation method and application of the fluorescent probe. The fluorescent probe is subjected to fluorescence quenching by taking near infrared fluorescent parent nucleus containing a plurality of double bonds as a fluorophore and taking 2,4-dinitrobenzene sulfonamide as a quenching unit; in actual detection, in thepresence of the cysteine, sulfydryl of the cysteine carries out nucleophilic substitution reaction on electron deficient aromatic ring, a sulfonamide bond cracks and a fluorescence quencher is dissociated, so that the fluorescent probe without fluorescence or with weak fluorescence based on intramolecular charge transfer (ICT) process releases the fluorescent parent nucleus, fluorescence is enhanced or opened to generate a fluorescent signal for selectively recognizing the cysteine, and further the aims of selective recognition and analysis and detection of the cysteine (Cys) are achieved.

Description

technical field [0001] The invention relates to the technical field of chemical analysis and detection, in particular to a fluorescence "off-on" near-infrared fluorescent probe for detecting cysteine, a preparation method and application thereof. Background technique [0002] There are a variety of important small molecule sulfhydryl compounds in organisms, and cysteine ​​(Cys) is the only natural essential amino acid containing sulfhydryl (-SH), and is an important component of protein synthesis. The content of cysteine ​​in the body is closely related to many physiological diseases, such as Alzheimer's disease and cardiovascular disease. Therefore, the content of cysteine ​​can be used as one of the basis for the diagnosis of such diseases. At the same time, a detailed understanding of the generation, distribution and level fluctuation of cysteine ​​(Cys) is of great significance to the research of cell activity, body physiology and pathology. Important scientific signifi...

Claims

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Application Information

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IPC IPC(8): C07C311/21C07C303/38C07D295/112C07D295/155C09K11/06A61K49/00G01N21/64
CPCA61K49/0021C07C303/38C07C311/21C07D295/112C07D295/155C09K11/06C09K2211/1007C09K2211/1044G01N21/6428G01N2021/6432
Inventor 肖光汉
Owner 湖南汇百益新材料有限公司
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