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A dual brain tumor targeting lipid material and its application

A technology of targeting lipids and targeting liposomes, applied in the field of medicine, can solve the problems of limited targeting ability, limited improvement, and inability of drugs to reach more brain tumor tissues.

Active Publication Date: 2021-06-01
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Glucose or RGD peptide-modified liposomes can improve the brain tumor targeting of drugs to a certain extent and promote the accumulation of drugs in tumor tissues, but this improvement is still very limited.
This may be due to the limited targeting ability of a single targeting molecule modification, resulting in the inability of the drug to reach more brain tumor tissues

Method used

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  • A dual brain tumor targeting lipid material and its application
  • A dual brain tumor targeting lipid material and its application
  • A dual brain tumor targeting lipid material and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of Compound 2

[0038]

[0039] Add succinic anhydride 1 (5.00 g, 49.96 mmol), benzyl alcohol (5.94 g, 54.96 mmol) and 4-dimethylaminopyridine (DMAP, 61 mg, 0.50 mmol) into 50 mL of tetrahydrofuran, heat up to 50 °C The reaction was stirred for 5 hours. Remove the solvent under reduced pressure, add 100 mL of ethyl acetate to the residue, wash with saturated sodium bicarbonate (100 mL), discard the organic layer, adjust the aqueous layer to pH = 2 with dilute hydrochloric acid (1 mol / L), and filter , the filter cake was dried to obtain 6.58 g of white solid, yield 63.29%, Mp: 60-62 o c.

Embodiment 2

[0041] Preparation of Compound 4

[0042]

[0043] Anhydrous glucose 3 (Glu, 18.02 g, 0.10 mol) was dissolved in 230 mL of anhydrous pyridine, and after cooling in an ice bath for 5 minutes, trimethylchlorosilane (TMSCl, 76.06 mL, 0.60 mol) and hexamethyl A mixed solution of disilazylamine (HDMS, 62.88 mL, 0.30 mol) was slowly added dropwise to the above pyridine solution, and stirred at room temperature for 24 hours. Remove the solvent under reduced pressure, add 200 mL of water to disperse, extract the aqueous layer with diethyl ether (200 mL×2), combine the organic layers, and successively wash with dilute hydrochloric acid (1mol / L, 200 mL×2), saturated aqueous sodium chloride (200 mL×2) 2) Washing, drying with anhydrous sodium sulfate, and removing the solvent under reduced pressure to obtain 52.87 g of a yellow oil, with a yield of 97.70%. The product can be directly subjected to the next reaction without purification.

Embodiment 3

[0045] Preparation of compound 6

[0046]

[0047] Compound 4 (10.99 g, 20.31 mmol) was dissolved in a mixed solution of acetone and methanol (5:8, 65 mL), and acetic acid (2.1 mL, 36.72 mmol) in acetone and methanol (5:8) was slowly added dropwise under ice cooling. 8, 6.5 mL) mixed solution. After the dropwise addition, the reaction solution was moved to room temperature and stirred for 2 hours, and sodium carbonate powder (3.30 g, 31.14 mmol) was added to continue stirring at room temperature for 20 minutes. The white solid was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate=50 / 1) to obtain 7.40 g of a colorless oil with a yield of 77.65%. 1 H NMR (400 MHz, CDCl 3 , ppm) δ :0.12-0.18 (m, 36H), 3.31-0.34 (m, 1H), 3.37 (dd, 1H, J = 2.8 Hz, 9.2 Hz), 3.55 (t, 1 H, J = 8.8 Hz), 3.62-3.64 (m, 3H), 3.79 (t, 1 H, J = 8.8 Hz), 5.02(d, 1 H, J = 2....

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Abstract

The invention discloses a novel lipid material, which is used for prolonging the circulation time and increasing the targeted delivery of drugs to brain tumor tissues. The new lipid material is bridged with polyethylene glycol, one side is connected with cholesterol, and the other side is connected with glucose and RGD peptide, which makes up for the lack of brain tumor targeting ability of liposomes modified by single glucose or RGD peptide, and realizes trans Efficient targeting of brain tumors behind the blood-brain barrier. This new type of lipid material can be used in different dosage forms including liposomes, nanoparticles, micelles, etc. The prepared paclitaxel-loaded liposomes have obvious brain tumor targeting functions and have broad application prospects.

Description

technical field [0001] The present invention relates to a new type of lipid material and its application in the drug delivery system, which has the functions of prolonging the internal circulation and double brain tumor targeted drug delivery, including the preparation of the material and its function as a drug carrier in drug delivery The application belongs to the technical field of medicine. Background technique [0002] According to statistics, about 1 / 5 of the world's population suffers from various types and degrees of central nervous system (CNS) diseases, including brain tumors, acute or chronic pain syndrome, epilepsy, encephalitis, cerebral ischemia and neurodegeneration Diseases (e.g. Alzheimer's, Parkinson's, etc.). As the world's population ages, this trend will intensify and have serious implications for human health. The existence of the blood-brain barrier (BBB) ​​has a certain protective effect on the human central nervous system, but it also restricts man...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/24A61K47/54A61K47/64A61K31/337A61K47/69A61P35/00
CPCA61K31/337A61K47/24A61K47/549A61K47/64A61K47/6911A61P35/00
Inventor 吴勇海俐郭丽赵毅乐其明陈洋付秋旖
Owner SICHUAN UNIV
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