Preparation and application of multi-branch biotin modified breast cancer targeted liposomes

A technology targeting lipids and biotin, applied in the field of medicine

Inactive Publication Date: 2020-03-27
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, for the surface ligand functionalization of nanocarriers, researchers have focused on the types of ligands, such as comparing the targeting capabilities of different ligands or introducing multiple ligands simultaneously to impro...

Method used

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  • Preparation and application of multi-branch biotin modified breast cancer targeted liposomes
  • Preparation and application of multi-branch biotin modified breast cancer targeted liposomes
  • Preparation and application of multi-branch biotin modified breast cancer targeted liposomes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Preparation of Compound 2

[0040] Diethanolamine 1 (1 g, 9.51 mmol) was dissolved in 30 mL of acetonitrile, di-tert-butyl dicarbonate (2.49 g, 11.41 mmol) was added with stirring at room temperature, and the reaction was continued at room temperature for 4 hours, monitored by TLC. After the reaction was complete, it was concentrated under reduced pressure, and the residue was purified by silica gel flash column chromatography (petroleum ether: ethyl acetate = 5:1) to obtain 1.82 g of compound 2 as a colorless oil with a yield of 93.50%. 1 H NMR (400 MHz, CDCl 3 , ppm) δ: 1.47 (s, 9H), 2.83 (s, 2H), 3.44 (d,4H, J= 11.6 Hz), 3.80 (s, 4H).

Embodiment 2

[0042] Preparation of compound 3

[0043] Biotin (2.38 g, 9.76 mmol) was dissolved in a mixed solvent of dichloromethane and N, N-dimethylformamide (v / v=45 mL / 15mL), and EDCI (2.80 g, 14.61 mmol), DMAP (1.78 g, 14.61 mmol) and DIPEA (4.84 mL, 29.28 mmol) were added dropwise to 10 mL of compound 2 (500 mg, 2.44 mmol) in dichloromethane under stirring at room temperature. The reaction was carried out at room temperature for 10 hours, monitored by TLC. After the reaction is complete, wash the reaction solution with 1N hydrochloric acid solution (50 mL × 1), saturated NaCl solution (50 mL × 8) successively, anhydrous NaCl 2 SO 4 After drying, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel flash column chromatography (dichloromethane:methanol=30:1) to obtain 1.24 g of a light yellow solid with a yield of 77.33%. mp: 108-110 °C. 1 H NMR (400 MHz, CDCl 3 , ppm)δ: 1.26-1.29 (m, 4H), 1.47(s, 9H), 1.65-1.76 (m, 8H), 2.38 (s, 4H),...

Embodiment 3

[0045] Preparation of Compound 4

[0046] 3.22 g of compound 3 was dissolved in 20 mL of dichloromethane, and 10 mL of trifluoroacetic acid was added. After reacting at room temperature for 4 hours, the reaction solution changed from yellow to brick red, and the reaction was complete as monitored by TLC. Concentrate under reduced pressure to remove dichloromethane and trifluoroacetic acid to obtain 3.47 g of dark green oil, add 30 mL of glacial diethyl ether to precipitate a light yellow solid, centrifuge and dry to obtain 2.94 g of light yellow trifluoroacetate compound 4.

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Abstract

The invention discloses novel lipid materials for realizing the delivery of breast cancer targeted drugs. According to the novel lipid materials, through a branch framework, one end is connected to cholesterol extended by polyethylene glycol, and the other end is connected to a different number of biotins with a breast cancer targeting function; and affinity between the novel lipid materials and areceptor can be used to realize stronger tumor targeting and play a more effective role in breast cancer treatment. The novel lipid materials can be used in different dosage forms such as liposomes,nanoparticles and micelles, and the prepared paclitaxel-loaded liposomes have obvious breast cancer targeting and broad application prospects.

Description

technical field [0001] The invention relates to a new type of lipid material and its application in drug delivery system, which has the function of breast cancer targeted drug delivery, including the preparation and characterization of the material, and its application as a drug carrier in drug delivery, belonging to field of medical technology. Background technique [0002] Breast cancer is one of the common malignant tumors in women, which seriously affects the survival and quality of life of women, and is known as the number one killer of women's health. According to the national cancer statistics released by the National Cancer Center in 2018, breast cancer ranks first in the incidence of malignant tumors in women. Moreover, on a global scale, the incidence of breast cancer among women in both developed and developing countries ranks first. According to statistics, the global incidence of breast cancer has been on the rise since the late 1970s, and the age of onset is ...

Claims

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Application Information

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IPC IPC(8): A61K9/127A61K47/22A61K47/28A61K47/24A61K31/337A61P35/00
CPCA61K9/127A61K31/337A61K47/22A61K47/24A61K47/28A61P35/00
Inventor 吴勇海俐郭丽乐其明蒲妍池彭瑶
Owner SICHUAN UNIV
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