Target membrane micromolecule and preparation method and application thereof

A technology of small molecules and target membranes, applied in chemical instruments and methods, medical preparations containing active ingredients, pharmaceutical formulations, etc., can solve the problem of low yield of near-infrared fluorescent probes and the inability to achieve reliability in the second near-infrared region Fluorescent labeling and other issues

Pending Publication Date: 2022-04-29
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with traditional fluorescent probes, NIRF probes have deeper tissue penetration, which is beneficial for in vivo and in vitro imaging, but the yield

Method used

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  • Target membrane micromolecule and preparation method and application thereof
  • Target membrane micromolecule and preparation method and application thereof
  • Target membrane micromolecule and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Preparation of Intermediate 1

[0029]

[0030] Dissolve 1-bromo-3,4,5-trimethoxybenzene (5.0 g, 1.0 eq) in 100 mL of dichloromethane, evacuate nitrogen and cool it to -78 °C in a dry ice / acetone bath for about 30 min, Boron tribromide (20.0 g, 4.0 eq) was added dropwise and incubated at -78 °C for 30 min, then the solution was slowly warmed to 40 °C. After 24 h of reaction, saturated aqueous ammonium chloride solution was added to quench the reaction, the mixture was filtered and washed with ethyl acetate, then the filtrate was extracted with ethyl acetate, the organic phase was dried over magnesium sulfate and separated and purified using silica gel column chromatography (ethyl acetate). : n-hexane=3:10) to obtain Intermediate 1.

Embodiment 2

[0031] Example 2: Preparation of Intermediate 2

[0032]

[0033] Potassium carbonate (4.0 g, 6.0 eq) and intermediate 1 were dissolved in 100 mL of acetone, and nitrogen was sparged under vacuum, and 5-bromo-1,2,3-phloroglucinol (1.0 g, 1.0 eq) was added, and the mixture was heated at 90 °C. Heat to reflux and stir for 24h. After the reaction was completed, it was extracted with dichloromethane and separated and purified by silica gel column chromatography (petroleum ether:ethyl acetate=10:1) to obtain Intermediate 2.

Embodiment 3

[0034] Example 3: Preparation of Intermediate 3

[0035]

[0036] Intermediate 2 (1.0g, 1.0eq) and potassium acetate (0.4g, 2.5eq), pinacol biboronate (0.6g, 1.3eq), catalyst 1 × 1' bis(triphenylphosphine) dimethylene Ferric palladium chloride (24.0 mg) was added to the reaction flask, 20.0 mL of 1,4-dioxane was added, and nitrogen was sparged under vacuum, and the reaction was carried out at 100° C. for 2 h. After completion of the reaction, extract with dichloromethane, spin dry, and use silica gel column chromatography for separation and purification (petroleum ether:dichloromethane=10:2) to obtain Intermediate 3.

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Abstract

The invention relates to a multifunctional target membrane micromolecule BBT, a preparation method thereof and application of the multifunctional target membrane micromolecule BBT in preparation of anti-cancer drugs. According to the method, a final product BBT is obtained by modifying an initial raw material 1-bromo-3, 4, 5-trimethoxybenzene through a methoxy removal reaction, a halogen replacement reaction and the like, and the method is simple to operate, high in yield and low in loss. The prepared BBT has an efficient cell embedding effect, can realize near-infrared two-region fluorescence labeling, can effectively induce cell apoptosis and inhibit tumor growth, and has good chemotherapy and photothermal therapy effects.

Description

technical field [0001] The invention relates to the technical field of anticancer drugs, in particular to a multifunctional target membrane small molecule BBT used for cancer treatment and a preparation method and application thereof. Background technique [0002] Chemotherapy is one of the widely used forms of current cancer treatment, mainly through chemotherapy drugs to achieve the purpose of controlling and killing cancer cells. Chemotherapy drugs can be circulated in most tissues and organs in the body, and can be applied to the treatment of metastatic tumors. But it can cause a range of side effects, including fatigue, nausea, vomiting, hair loss, and decreased blood cells. Photothermal therapy is an emerging cancer treatment method. It refers to injecting photothermal materials into the body, focusing on the tumor site through targeted recognition technology, and converting light energy into heat energy under the irradiation of an external light source to kill cancer...

Claims

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Application Information

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IPC IPC(8): C07D513/04C09K11/06A61K41/00A61K49/00A61P35/00G01N21/64
CPCC07D513/04C09K11/06A61K41/0057A61K49/0021A61P35/00G01N21/6428C09K2211/1081C09K2211/1092C09K2211/1007
Inventor 鲍碧清刘天琪汪联辉周陆瑶
Owner NANJING UNIV OF POSTS & TELECOMM
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