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Polyethylene glycol-cyclooctyne derivatives

A polyethylene glycol and derivative technology, applied in the field of gel, polyethylene glycol-cyclooctyne active derivatives, can solve the problems of non-water solubility and limited application

Active Publication Date: 2017-12-01
JENKEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most traditional cyclooctyne reagents do not have good water solubility, which limits their application in biomedicine to a certain extent.

Method used

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  • Polyethylene glycol-cyclooctyne derivatives
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  • Polyethylene glycol-cyclooctyne derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Example 1: Preparation of Polyethylene Glycol (5000Da)-(Cyclooctyne-2-Oxygen)-Acetamide

[0073]

[0074] Dissolve 0.87g of cyclooctyne-2-oxoacetic acid and 0.64g of N-hydroxysuccinimide (NHS) in 20ml of dichloromethane, and add N,N'-dicyclohexylcarbodiimide ( DCC) 1.22g, reacted for 4h, dissolved 10.0g of polyethylene glycol (5000Da)-ethylamine in 80ml of dichloromethane, added to the reaction bottle, reacted overnight, filtered, concentrated at 40°C, heated to dissolve the ice with 150ml of isopropanol Precipitate in a water bath, filter, wash the filter cake twice with isopropanol, and dry in vacuum to obtain 9.3 g of polyethylene glycol (5000 Da)-(cyclooctyne-2-oxy)-acetamide.

[0075] 1 H-NMR (DMSO) δ: 1.44-2.33 (m, CH 2 ring,20H),4.26(m,CH ring,2H)

Embodiment 2

[0076] Example 2: Preparation of methoxypolyethylene glycol (5000Da)-(cyclooctyne-2-oxo)-acetamide

[0077]

[0078] Dissolve 0.44g of cyclooctyne-2-oxoacetic acid and 0.34g of N-hydroxysuccinimide (NHS) in 10ml of dichloromethane, and add N,N'-dicyclohexylcarbodiimide ( DCC) 0.62g, react for 4h, dissolve 10.0g of methoxypolyethylene glycol (5000Da)-ethylamine in 90ml of dichloromethane, add to the reaction bottle, react overnight, filter, concentrate at 40°C, and use 150ml of isopropanol Heat to dissolve the precipitate in an ice-water bath, filter, wash the filter cake twice with isopropanol, and vacuum-dry to obtain 9.5 g of methoxypolyethylene glycol (5000 Da)-(cyclooctyne-2-oxo)-acetamide.

[0079] 1 H-NMR (DMSO) δ: 1.44-2.33 (m, CH 2 ring,10H),4.26(m,CH ring,1H)

Embodiment 3

[0080] Example 3: Preparation of methoxypolyethylene glycol (10000Da)-ethylcarbamate-(bicyclo[6.1.0]nonon 4-yne)-9-methyl ester

[0081]

[0082] Dissolve 1.0 g of methoxypolyethylene glycol (10000 Da)-ethylamine in 10 ml of dichloromethane, and under nitrogen protection, (bicyclo[6.1.0]nonon 4-yne)-9-methoxycarbonyl-succinyl imidate Add 0.032g into the reaction flask, react overnight, filter, concentrate at 40°C, heat with 20ml of isopropanol to dissolve the precipitate in an ice-water bath, filter, wash the filter cake twice with isopropanol, and dry in vacuum to obtain methoxypolyethylene glycol (10000Da 0.9 g of )-ethylcarbamate-(bicyclo[6.1.0]nonon-4-yne)-9-methyl ester.

[0083] 1 H-NMR(DMSO)δ: 0.86-2.23(m, CH 2 ring,8H),1.26(t,CH,1H),4.01(d,CH 2 -O,2H)

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Abstract

The present invention provides a polyethylene glycol-cyclooctyne derivative of general formula I, characterized in that the polyethylene glycol-cyclooctyne derivative comprises PEG, a cyclooctyne end group Q and a A linking group X to the cyclooctyne end group Q. This polyethylene glycol-cyclooctyne derivative can undergo a copper-free click reaction with azide compounds, and has good water solubility, and has good applications in drug synthesis, drug sustained release, and functional materials. prospect. The present invention also provides gels obtained by copolymerizing the reactive derivatives with other polymer precursors.

Description

technical field [0001] The invention relates to a polyethylene glycol derivative, in particular to a polyethylene glycol-cyclooctyne active derivative with a cyclooctyne chain end, and a gel prepared from the active derivative. Background technique [0002] Polyethylene glycol is a polyether polymer compound with a wide range of uses. It can be used in many fields such as medicine, hygiene, food, and chemical industry. Polyethylene glycol can be dissolved in water and many solvents, and the polymer has excellent biocompatibility, can be dissolved in interstitial fluid in the body, and can be quickly excreted by the body without any toxic side effects. [0003] In the application of polyethylene glycol, the end group plays a decisive role, and polyethylene glycol with different end groups has different uses. The macromolecular chain segment of polyethylene glycol is not limited to the terminal hydroxyl group, and the active derivatives of polyethylene glycol obtained by intr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/48C08G81/00
Inventor 陈晓萌林美娜赵宣
Owner JENKEM TECH