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Novel bis-amidogen phosphoryl choline compound Lys-EG-PC and preparation method thereof

A phosphorylcholine compound technology, applied in the field of novel diamino phosphorylcholine compound Lys-EG-PC and its preparation, can solve the problems of low reactivity, non-stable existence for a long time, low reaction rate, etc. Achieve the effects of improving activity and stability, improving biocompatibility, and inhibiting protein adsorption

Inactive Publication Date: 2017-04-19
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Without the help of amino groups, the reaction rate of these compounds will be very low, so long-term and high-temperature reaction conditions are required, or grafting cannot be performed.
[0005] Therefore, patent document 4 (CN201180062050.7) discloses a phosphorylcholine compound containing a monoamino group and a preparation method thereof, but the application of such compounds still has limitations
This type of compound has only a single amino functional group, and can only be used as a surface treatment agent for grafting on the surface of the substrate, and its reactivity is low, so it cannot exist stably for a long time. In addition, due to the limitation of single amino group, this type of compound cannot be used as a chain extender. or cross-linking agents, thereby failing to enhance biocompatibility from the bulk of the material

Method used

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  • Novel bis-amidogen phosphoryl choline compound Lys-EG-PC and preparation method thereof
  • Novel bis-amidogen phosphoryl choline compound Lys-EG-PC and preparation method thereof
  • Novel bis-amidogen phosphoryl choline compound Lys-EG-PC and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0038] Step 1. Dissolve 0.132mol of Cbz-Cl in 100mL of diethyl ether solution, add dropwise 200mL of 10% NaCO containing 0.055molL-lysine 3 After the dropwise addition, keep the temperature at 0°C for 5 hours. The obtained product is acidified with an appropriate amount of 10% citric acid and then extracted with chloroform. After the product is washed with water, it is evaporated to dryness to obtain a large amount of N,N'-bisbenzyloxycarbonyl-L- Lysine, about 93% yield.

[0039] Step 2. Add 0.055mol of N,N'-bisbenzyloxycarbonyl-L-lysine into a dry 500mL three-necked flask, add 0.11mol of triethylamine acid-binding agent and 200mL of anhydrous tetrahydrofuran, mix well, and put Dissolve 0.145 mol of thionyl chloride in 50 mL of acetone, put it into a constant pressure dropping funnel, and set a mechanical stirrer at -15°C to control the rate of addition of thionyl chloride. After about 2 hours, the addition of thionyl chloride is completed. After about 2 hours after the reacti...

specific example 2

[0044] Step 1. Add 0.055mol of L-lysine and 0.11mol of triethylamine into a 500ml dry three-neck flask, preferably dissolve in 200mL of tetrahydrofuran, keep the reaction temperature at -15°C, and slowly add the solution dropwise under mechanical stirring. Add 0.145 mol thionyl chloride in acetone, drop it within 2 hours, keep the temperature and continue the reaction for 2 hours; after raising the temperature to room temperature, slowly add 0.08 mol ethylene glycol dropwise, react for 6 hours, pour the reaction solution out and suction filter A light yellow solution was obtained, diethyl ether was used three times, and the solvent was evaporated to obtain the product with a yield of about 96%.

[0045] In step 2, 0.155 mol of Cbz-Cl was dissolved in 100 mL of diethyl ether solution, and 200 mL of 10% NaCO containing 0.0645 mol of compound (2) was added dropwise. 3 Aqueous solution, keeping the temperature at 0°C, reacting for 5 hours, the obtained product was acidified with a...

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Abstract

The invention discloses a novel bis-amidogen phosphoryl choline compound Lys-EG-PC and a preparation method thereof and aims to provide the phosphoryl choline compound capable of being used for a surface treating agent or a surface treating agent raw material. The compound of the type can furthermore directly serve as a dressing agent, a chain extender or a cross-linking agent for decorating surfaces of various base materials or modifying the base materials so as to improve blood compatibility of high molecular materials, lower protein adsorption and reduce cell sediment, and the compound has huge academic value and broad prospect in the fields of tissue engineering, drug controlled release, gene therapy, cosmetics and the like. Steps are simple, operation is convenient to perform, and practicability is high.

Description

technical field [0001] The invention belongs to the field of preparation of phosphorylcholine derivatives, in particular to a novel diamino phosphorylcholine compound Lys-EG-PC and a preparation method thereof. Background technique [0002] Phosphorylcholine is the hydrophilic end group of lecithin, which is the structural unit of the cell membrane. It is the outer functional group in the outer membrane of the cell. The surface with this structure and composition interacts with the physiological environment not only will not adsorb and deposit proteins, but also will not trigger platelet activation, leading to adverse reactions such as blood coagulation, and has good biocompatibility. Studies in recent years have shown that the use of phosphorylcholine groups and their polymers to construct an anti-external membrane structure on the surface of the material can reduce the adsorption of fibrinogen, and increase the matrix material by reducing the adhesion and activation of pla...

Claims

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Application Information

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IPC IPC(8): C07F9/09B01F17/18B01F17/16B01F17/14C08K5/521C09K23/14C09K23/16C09K23/18
CPCC07F9/091C08K5/5205C08K5/521C09K23/14Y02P20/55
Inventor 侯昭升贾骐
Owner SHANDONG NORMAL UNIV
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