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Anti-adsorption and long-circulation lipid molecule, preparation method and application thereof in fields of medicines and cosmetics

A molecular and lipid technology, applied in the field of phospholipids as a pharmaceutical carrier material, can solve problems such as difficulty in meeting multiple modifications

Active Publication Date: 2012-09-05
INST OF PROCESS ENG CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, in DSPE-PEG molecules, only the hydroxyl groups at the ends of PEG molecules can be used for modification, which is difficult to meet the needs of multiple modifications

Method used

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  • Anti-adsorption and long-circulation lipid molecule, preparation method and application thereof in fields of medicines and cosmetics
  • Anti-adsorption and long-circulation lipid molecule, preparation method and application thereof in fields of medicines and cosmetics
  • Anti-adsorption and long-circulation lipid molecule, preparation method and application thereof in fields of medicines and cosmetics

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Synthesis of CBMA (compound (II))

[0060] Weigh 0.664g (3.97mmol) DMAEMA in a Schlenk bottle, and use N 2 Replace the oxygen in the bottle, in N 2 Under protection, add 20 mL of anhydrous dichloromethane with a disposable needle. After stirring at 25°C for about 10min, 0.343g (4.77mmol) of β-propiolactone was added rapidly, and stirred at 25°C for 5h. At the end of the reaction, use a rotary evaporator to remove the dichloromethane solvent, add an appropriate amount of acetone, and filter with suction to obtain a white solid, which is then washed with dichloromethane and ether, and dried in vacuo to obtain 0.8673 g of a white solid. figure 1 .

Embodiment 2

[0062] Synthesis of DSPE-Br (compound (III))

[0063] Take 0.2972g (0.40mmol) of DSPE in a flask, add 20mL of anhydrous dichloromethane and 0.0810g (0.80mmol) of triethylamine, and stir at 25°C for 1h. Add 0.1563g (0.68mmol) 2-bromo-2-methylpropionyl bromide to the above flask, heat to 45°C, condense and reflux for 12 hours. Transfer the reaction solution into a separatory funnel, add an equal volume of water to wash, and wash repeatedly 3 times. Add anhydrous sodium sulfate to the organic phase to dry, filter, and concentrate the filtrate to obtain 0.2674 g of a white solid, whose structural characterization is shown in the attached figure 2 .

Embodiment 3

[0065] Synthesis of DSPE-PCBMA (compound I)

[0066]Taking the synthesis of PCBMA with a theoretical degree of polymerization of 50 as an example to illustrate the polymerization process of DSPE-PCBMA. Weigh 0.0358g (0.04mmol) of the DSPE-Br prepared in Example 2 and dissolve it in 2mL of dichloromethane, weigh 0.4586g (2.00mmol) of the CBMA prepared in Example 1 and dissolve it in 20mL of absolute ethanol, after mixing Add it to a clean dry Schlenk flask, add 12.0mg (0.08mmol) Cu(I)Br, and perform three freeze-thaw cycles to degas. Then measure 0.0139g (0.08mmol) PMDETA in 1mL of absolute ethanol, inject the solution into the frozen above reaction system, and then perform three freeze-thaw cycle degassing. The sealed reaction system was reacted at 60°C for 24 hours. The product was dialyzed in an osmotic bag with a molecular weight cut-off of 3500, respectively, using absolute ethanol and deionized water as the external phase, and freeze-dried to obtain 0.2173 g of a white ...

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Abstract

The invention relates to a lipid molecule, namely poly-carboxyl oxyneurine (R1-L-PCB), which is represented by the formula (I), and a preparation method and application thereof. The method for preparing the R1-L-PCB comprises the following steps of: reacting the lipid molecule with halogenated hydrocarbon to obtain R1-L-X, (II) for short; and then with the R1-L-X as an initiator and carboxyl oxyneurine CB as a monomer, performing polymerization reaction on an atom transfer radical to obtain the R1-L-PCB, (I) for short. The R1-L-PCB lipid molecule derivate has high nonspecific protein adsorption resistance performance, can be used in nonspecific protein adsorption of a liposome, is favorable for improving the stability and the transferring efficiency of the liposome and can be applied to the fields of medicines, cosmetics and the like.

Description

technical field [0001] The invention relates to a pharmaceutical carrier material phospholipid, in particular, the invention relates to a lipid molecule-polycarboxybetaine, its preparation method and its application. Background technique [0002] Liposome is a molecular orderly assembly formed spontaneously by phospholipids in water by hydrophobic association, and is a multilamellar vesicle structure. Liposomes have the advantages of good biocompatibility, low toxicity, and low immune response. At present, liposomes are used to encapsulate hydrophobic drugs, hydrophilic drugs and genetic drugs, etc. After intravenous injection, liposomes can effectively delay drug release and improve bioavailability, and are widely used in the fields of medicine and cosmetics. [0003] During blood circulation, liposomes are prone to non-specific adsorption with serum proteins, forming large-sized aggregates, which are easily cleared by the mononuclear phagocyte system (MPS), resulting in s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F122/22C08F4/00C07F9/09A61K47/16A61K47/22A61K47/24A61K47/28A61K47/34
Inventor 张欣李燕代凤英
Owner INST OF PROCESS ENG CHINESE ACAD OF SCI
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