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A kind of biotin-labeled naringin, preparation method and application thereof

A technology of biotin labeling and naringin, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of unclear drug targets of naringin, achieve good anti-inflammatory effect, and simple preparation method Effect

Active Publication Date: 2021-11-23
HUAZHONG AGRI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, the good anti-inflammatory function of naringin has been widely concerned, but the drug target of naringin is still unclear, and there are few reports as an anti-inflammatory drug

Method used

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  • A kind of biotin-labeled naringin, preparation method and application thereof
  • A kind of biotin-labeled naringin, preparation method and application thereof
  • A kind of biotin-labeled naringin, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0037] The preparation of the naringin of embodiment 1 biotinylation

[0038](1) Add 2.6g of naringin, 30mg of 4-toluenesulfonamide (PTSA) and 15mL of organic solvent N,N-dimethylformamide DMF into a round bottom flask, and stir to dissolve it. Add 2.6 g of p-bromobenzaldehyde dimethyl acetal, and react at 35°C for 12-24 hours, 20 hours in this example. In this step of other embodiments, the amount of each substance can meet the following conditions: the molar ratio of naringin, PTSA and p-bromobenzaldehyde dimethyl acetal is 25-45:1:50-80; naringin and organic solvent The mass-to-volume ratio of naringin is 1:5-10, that is, the volume of organic solvent per gram of naringin is 5-10 milliliters.

[0039] After the reaction, DMF was distilled off under reduced pressure, and the residue was recrystallized from methanol to obtain compound 1 as a white solid with a yield of 40%. Carry out NMR analysis to the obtained white solid compound 1, 1 H NMR spectrum see figure 2 , the...

Embodiment 2

[0049] Example 2 Biotin-labeled naringin anti-inflammatory pharmacodynamics study

[0050] To test whether the substance still has anti-inflammatory activity after biotin-labeled naringin. Inflammation model of mouse macrophage RAW264.7 cells was established with lipopolysaccharide (LPS). RAW264.7 cells in the logarithmic growth phase were seeded in 24-well culture plates, and after one day of adherent growth, four different treatments were set, namely, the blank control group of RPMI-1640 medium without fetal bovine serum ; lipopolysaccharide LPS (1 μg / mL) treatment group; 50 μg / mL biotin-labeled naringin probe (Biotin-Naringin) and lipopolysaccharide LPS (1 μg / mL) treatment group; and naringin (50 μg / mL ) and lipopolysaccharide LPS (1 μg / mL). After 18 hours of drug treatment, remove the cell supernatant, add Trizol reagent, extract RNA according to the operation of the kit, and after reverse transcription, use real-time fluorescent quantitative PCR to detect the inflammato...

Embodiment 3

[0071] Example 3 Immunoprecipitation Screening for Binding Proteins of Naringin

[0072] In order to screen out the target protein specifically binding to naringin from mouse macrophages, the synthesized biotin-labeled naringin was used as a probe, and the method of immunoprecipitation was used for screening.

[0073] The procedure of immunoprecipitation assay is as follows: Figure 7shown. Take 60 μL of streptavidin agarose beads respectively in two 1.5 mL centrifuge tubes, add 500 μL of phosphate buffer saline (PBS) to each, and centrifuge to remove the supernatant (14000 g, 5 s). Add 500 μL of PBS and 4 μL of 1 μg / μL Biotin-Naringin and Biotin solutions respectively, and incubate at 4° C. for 1 h with shaking. After the incubation, centrifuge to remove the supernatant (14000g, 5s). Add 500 μL PBS and centrifuge and wash 3 times (14000g, 5s). Then add 500 μL of 1 μg / μL mouse macrophage total protein, and incubate at 4°C for 1 h with shaking. After the incubation, centri...

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Abstract

The invention belongs to the technical field of organic synthesis and medicinal chemistry, and in particular relates to a biotin-labeled naringin, a preparation method and an application thereof. The biotin-labeled naringin probe prepared by the present invention has the structural formula shown in formula (1), and the compound has a stable structure, simple synthesis and anti-inflammatory activity. Pharmacological experiments show that the biotin-labeled naringin probe of the present invention has better anti-inflammatory effect than independent naringin, and has the value of developing anti-inflammatory drugs; on the other hand, the biotin-labeled naringin It can be used as a molecular probe to explore the drug target of naringin, which is of great significance for exploring the mechanism of action of naringin in the inflammatory process.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and medicinal chemistry, and in particular relates to a biotin-labeled naringin, a preparation method and an application thereof. Background technique [0002] Biotin, also known as vitamin H and coenzyme R, is a water-soluble vitamin and also belongs to the vitamin B family. Biotin widely exists in various organisms in nature and is an essential element for human and animals to maintain health, hence the name. Avidin is a glycoprotein that can specifically bind to biotin. Both avidin and biotin can be combined with protein and fluorescein molecules without affecting the biological activity of the latter, so they are ideal labeling agents. [0003] Naringin belongs to dihydroflavonoids and is a natural product widely present in citrus fruits with biological activity and pharmacological effects. It has the ability to resist oxidation and scavenge free radicals, and participates in the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/07C07H1/00A61P29/00G01N21/64
CPCA61P29/00C07H1/00C07H17/07G01N21/6428
Inventor 马兆成李明程丽萍
Owner HUAZHONG AGRI UNIV
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