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Merocyanine fluorescent probe as well as preparation method and application thereof

A technology of fluorescent probes and cyanines, which is applied in the preparation and application fields of fluorescent probes, can solve the problems of shallow imaging depth and biological autofluorescence interference in imaging results, and achieve the effect of simple detection process.

Active Publication Date: 2022-05-27
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The emission wavelengths of the currently reported fluorescent probes for fatty liver imaging are mostly in the visible region, and the imaging depth is shallow, and the imaging results are easily interfered by the autofluorescence of organisms
Moreover, most of the traditional fatty liver imaging probes are intensity-variable probes, and the change of a single wavelength is easily affected by factors such as the local concentration of the probe.

Method used

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  • Merocyanine fluorescent probe as well as preparation method and application thereof
  • Merocyanine fluorescent probe as well as preparation method and application thereof
  • Merocyanine fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 Preparation of probe Cy-Mp:

[0033] (1) Synthesis of compound 2:

[0034]

[0035] At -10 °C, to the mixed solution containing 18 mL dichloromethane and 18 mL dimethylformamide was slowly added dropwise phosphorus oxychloride (15 mL, 161 mmol), the reaction continued to stir for 1 h, followed by the addition of cyclohexanone (4.5 mL, 43 mmol), the mixed solution was heated to 80 °C reaction for 24 h. After the end of the reaction, the reaction system was poured into ice water overnight, the product was filtered, washed with petroleum ether and cold water to obtain yellow compound 2 (4.9g, 66.1%).

[0036] (2) Synthesis of compound 4:

[0037]

[0038]Toluene (30 mL) was added in a round-bottom flask and 2,3,3-trimethyl-3H-indole (7.2 mL, 45 mmol) and iodoethane (6 mL, 75 mmol) were added and refluxed for 24 h. Cooled to room temperature, filter the product, with ethyl acetate, to obtain a red compound 4 (8.7g, 61.5%).

[0039] (3) Synthesis of compound 5:

[...

Embodiment 2

[0045] Example 2 Detection of solvent polarity:

[0046] (1) Preparation of probe solution: Weigh 5.6mg of probe Cy-Mp in a 10mL volumetric flask and use DMSO to prepare a solution of 1.0mmol / L.

[0047] (2) Polarity responsiveness experiments: Probe Cy-Mp emission spectra in different proportions of water (high polarity) and 1,4-dioxane (low polarity) mixed solution, such as Figure 5a As shown, the emission intensity of the probe at 810 nm increases with the polarity of the solution. The intensity of the emission peak at 740 nm increased first with the increase of the polarity of the solution and then weakened, and the intensity ratio of the two was F 810 / F 740 Can be a good indication of changes in the polarity of the solution ( Figure 5 b)。 The excitation wavelength of the probe Cy-Mp is 600 nm.

[0048] (3) Selective experiment: In order to study the anti-interference ability of probe Cy-Mp, add common species of life systems such as Cu to the probe (HEPES buffer: DMSO= 9:1, ...

Embodiment 3

[0049] Example 3: Fluorescent imaging detection of non-alcoholic fatty liver mice:

[0050] (1) Preparation of probe solution: Weigh 5.6mg of probe Cy-Mp in a 10mL volumetric flask and use DMSO to prepare a solution of 1.0mmol / L.

[0051] (2) Probe distribution experiment in mice: In order to study the distribution of probe Cy-Mp in mice, we injected the probe (20 μM, 100 μL) into the mouse body by tail vein injection method, dissected the mouse after one hour, took the heart, liver, spleen, lungs, kidneys for fluorescent imaging, and used 600 nm as the excitation light to collect the emission signal of 790 nm. as Figure 7 As shown, the probe is mainly enriched in the liver of mice.

[0052](3) In vivo imaging of fatty liver model mice: In order to study the fluorescence imaging distinction between probe Cy-Mp on normal mice and non-alcoholic fatty liver mice, we successfully constructed fatty liver disease mice by feeding and injecting dexamethasone sodium phosphate solution with...

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Abstract

The invention belongs to the technical field of preparation and application of fluorescent probes, and particularly relates to a merocyanine fluorescent probe as well as a preparation method and application thereof. The merocyanine fluorescent probe provided by the invention can be used for solvent polarity detection and non-alcoholic fatty liver detection and diagnosis, and the detection process is simple, convenient and reliable.

Description

Technical field [0001] The present invention belongs to the field of fluorescent probe preparation and application technology, specifically relates to a kind of partial flower cyanide fluorescent probe, preparation method and application. Background [0002] Non-alcoholic fatty liver disease has become the most common chronic liver disease, accounting for about 25% of the total population. If timely and effective intervention is not carried out, non-alcoholic fatty liver disease is easy to develop into cirrhosis and even liver cancer. Therefore, it is of great significance to achieve early diagnosis of non-alcoholic fatty liver disease. Excessive accumulation of fat in fat cells is an important cause of fatty liver. At present, the diagnosis of non-alcoholic fatty liver is mainly achieved by B-ultrasound imaging, but it is limited by the limitations of acoustic imaging and its resolution is low. In contrast, fluorescence detection has the advantages of high sensitivity, real-time...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/08C09K11/06G01N21/64
CPCC07D401/08C09K11/06G01N21/6428G01N21/6458C09K2211/1029
Inventor 葛景园马尧庚陈忠研陈静黄文静陈玉洁
Owner WENZHOU UNIVERSITY