Diamido-terminated phosphorylcholine modified polyethylene glycol compound and preparation method thereof

A technology of diaminophosphorylcholine and bisaminophosphorylcholine is applied in the field of terminal diaminophosphorylcholine modified polyethylene glycol compound and preparation thereof, and can solve the problem of main chain modification of polymer biomaterials, Lack of flexible chains, difficult surface grafting, etc., to achieve the effect of improving biocompatibility and reducing adsorption

Inactive Publication Date: 2017-10-20
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, the patent document CN102070780B discloses a polyethylene glycol phosphorylcholine compound. Although various functional groups are introduced, when chemically bonding with the substrate surface treatment agent, there is no complementary functional group on the substrate surface. The reaction rate will be very low, so long-term and high-temperature reaction conditions are required, resulting in damage to the substrate, or grafting cannot be performed
Patent document CN106565772A discloses a terminal bisaminophosphorylcholine compound, but it lacks a flexible chain and is not easy to self-assemble on the surface of the material, resulting in low utilization of phosphorylcholine groups, so the biocompatibility of the matrix material not ideal
[0006] Therefore, although the poly(ethylene glycol) with PC group and PEG molecule combined to prepare the end-linked PC group meets the requirements of long-term implantation biomaterials (especially blood contact) in clinical bioenvironmental compatibility requirements, but at this stage The lack of activity of the end-capping group of this type of compound limits the application of this type of compound in the field of biomaterials, and there are still problems such as main chain modification of polymer biomaterials and difficulties in surface grafting.

Method used

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  • Diamido-terminated phosphorylcholine modified polyethylene glycol compound and preparation method thereof
  • Diamido-terminated phosphorylcholine modified polyethylene glycol compound and preparation method thereof
  • Diamido-terminated phosphorylcholine modified polyethylene glycol compound and preparation method thereof

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Effect test

Embodiment 1

[0051] Step 1: Dissolve 1 mol of monoamino-terminated polyethylene glycol, n=10, in N,N-dimethylformamide, add 1.2 mol of hexanoylphosphorylcholine compound, and react at 50°C for 12 hours, After cooling down to 8°C, add NaBH with a concentration of 0.02g / mL 4 Methanol solution (wherein NaBH 4 The amount of the substance is 2.4mol), adjust the reaction temperature to 20°C, react for 12h, and settle with ether to obtain polyethylene glycol with a phosphorylcholine group at the end.

[0052]

[0053] Step 2: Add 0.055 mol of N,N'-bisbenzyloxycarbonyl-L-lysine into a dry reaction flask, add 0.11 mol of triethylamine and 200 mL of tetrahydrofuran and mix well, then add 0.145 mol of dichlorohydrin Dissolve sulfone in 50mL of acetone, adjust the reaction temperature to -10°C, control the drop rate of the thionyl chloride solution, dropwise add in 2h, continue to react for 2h, rise to room temperature, and then continue to dropwise add 0.08mol end-connected phosphoryl The tetrah...

Embodiment 2

[0058] Step 1: Dissolve 1 mol of monoamino-terminated polyethylene glycol, n=50, in N,N-dimethylformamide, add 1.2 mol of formylphosphorylcholine compound, and react at 50°C for 12h, After cooling down to 8°C, add NaBH with a concentration of 0.02g / mL 4 Methanol solution (wherein NaBH 4 The amount of the substance was 2.4 mol), the reaction temperature was adjusted to 20° C., and the reaction was carried out for 12 hours, and the ether was precipitated to obtain polyethylene glycol end-connected with phosphorylcholine.

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Abstract

The invention discloses diamido-terminated phosphorylcholine modified polyethylene glycol and a preparation method thereof. Diamido is introduced into the terminal on the basis of phosphorylcholine modified polyethylene glycol, so that the diamido-terminated phosphorylcholine modified polyethylene glycol has high biocompatibility, the degradation product is non-toxic and can be absorbed and metabolized by an organism, and the application space of the phosphorylcholine modified polyethylene glycol is widened. Compared with the diamido-terminated phosphorylcholine compound, the diamido-terminated phosphorylcholine modified polyethylene glycol disclosed by the invention has the advantages that phosphorylcholine groups are easily self-assembled on the material surface due to flexible chains, and the preparation method is simple, rapid, easy to purify and low in cost.

Description

technical field [0001] The invention belongs to the technical field of biomaterials, in particular to the field of biocompatibility modification of biomedical polymer materials, in particular to a diaminophosphorylcholine-terminated polyethylene glycol compound and a preparation method thereof. Background technique [0002] With the rapid development of biotechnology, biomedical materials have become a hot spot in the current scientific research field. However, in the clinical application of existing biomedical materials and devices, problems such as infection, blood coagulation, and postoperative tissue hyperplasia exist to varying degrees. These biocompatibility problems have become key factors restricting the clinical application of biomedical materials. Currently, surface modification of materials is a very effective way to improve their biocompatibility. Generally speaking, the biocompatibility of materials can be improved by coating hydrophilic substances on the surfa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/322C08G65/333C08G65/335
CPCC08G65/33396C08G65/322C08G65/3356C08G2650/04
Inventor 侯昭升贾骐
Owner SHANDONG NORMAL UNIV
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