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A near-infrared fluorescent probe for detecting cys in the brain of depressed mice and its synthesis method and application

A technology of fluorescent probes and synthesis methods, applied in the field of synthesis of near-infrared fluorescent probes, to achieve the effect of simple operation methods, simple operation, and universal applicability

Active Publication Date: 2021-02-23
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the near-infrared imaging research on Cys has not been reported yet.

Method used

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  • A near-infrared fluorescent probe for detecting cys in the brain of depressed mice and its synthesis method and application
  • A near-infrared fluorescent probe for detecting cys in the brain of depressed mice and its synthesis method and application
  • A near-infrared fluorescent probe for detecting cys in the brain of depressed mice and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0037] A method for preparing a novel near-infrared fluorescent probe for detecting Cys in cells and living bodies, comprising the following steps:

[0038] Probe structure:

[0039]

[0040] Probe synthesis method:

[0041]

[0042] The structural formula of Changsha Red of the present application is as follows:

[0043]

Embodiment 1

[0047] Synthesis of compound b: under nitrogen protection conditions, 20mL DMF and 20mlCH 2 Cl 2 After mixing evenly, add 18ml POCl dropwise at 0°C 3 and 17mlCH 2 Cl 2 After the dropwise addition was completed, 2.65ml of cyclohexanone was added dropwise. After the dropwise addition, the reaction was transferred to an oil bath and reacted at 40°C for 3h. The reaction was quickly poured into crushed ice and kept overnight at 0°C. A yellow solid was obtained by suction filtration.

[0048] Synthesis of compound e: under nitrogen protection, 600 μL iodoethane and 800 μL indole were dissolved in 3 ml toluene, reacted at 80° C. for 12 h, cooled, precipitated and filtered to obtain a purple solid.

[0049] Synthesis of compound f: Mix 1.63g of product e, 0.45g of product b, 0.6g of sodium acetate, and 10ml of acetic anhydride under nitrogen protection, stir at room temperature for 24 hours in the dark, pour it into ether, and leave it to precipitate with a metallic luster green ...

Embodiment 2

[0054] The optical properties of the probe prepared in Example 1 were tested.

[0055] After adding Cys, the probe showed an absorption peak at about 700 nm ( figure 1 Middle A). Such as figure 1 As shown in B and C, under single-photon 590nm excitation, the fluorescence intensity of the probe at 710nm is weak, but after the probe is incubated with Cys, the fluorescence intensity of the probe at 710nm is significantly enhanced, and the fluorescence intensity varies with Cys concentration increased and enhanced. Such as figure 1 As shown in D, the linear range of the probe is 0-50 μM, and the detection limit is 0.45 μM.

[0056] Experiments of the invention in cells. The present invention first incubates PC12 cells with DTT (dithiothreitol) (increasing intracellular Cys) for 15 minutes, then adds a probe (10 μM) and then incubates for 2 minutes, and then uses PBS (phosphate-buffered saline) to remove residual extracellular The probes were washed away for fluorescence imag...

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Abstract

The invention relates to a method for synthesizing a near-infrared fluorescent probe for detecting Cys in the brain of depressed mice. Changsha red and phenyl thiochloroformate are uniformly mixed in a solvent and reacted to obtain the product. The invention is a near-infrared fluorescent probe which is nucleophilicly substituted by phenyl thioformate (a specific recognition group for Cys) and Changsha red (a fluorescent group). The invention has the advantages of simple preparation, sensitive detection, good selectivity and the like. It is worth noting that, using this invention, the present invention has successfully realized the imaging analysis of changes of Cys in the brain of depressed mice at the living level.

Description

technical field [0001] The invention belongs to the field of near-infrared fluorescent probe detection, and in particular relates to a synthesis method and application of a near-infrared fluorescent probe for detecting Cys in the brain of depressed mice. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Depression is a global mental disease with high prevalence, relapse rate, mortality rate and disability rate, which seriously endangers human health. Unfortunately, the current understanding of the pathophysiology of depression is still very imperfect. Existing studies have found that depression is closely related to oxidative stress-redox imbalance in the brain. In order ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/06C09K11/06A61K49/00
CPCA61K49/0021C07D405/06C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088
Inventor 唐波丁琪李平王昕张彦笛
Owner SHANDONG NORMAL UNIV
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