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Chain-functionalized multi-level branched polyethylene glycol and synthesis method thereof

A polyethylene glycol and chain functional technology, applied in the field of branched polyethylene glycol and its preparation, can solve the problems of low efficiency, inability to isolate proteins or polypeptides, etc.

Active Publication Date: 2012-03-07
XIAMEN SINOPEG BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 1) Since this technology only connects one end of polyethylene glycol to the protein or polypeptide, it cannot effectively isolate the protein or polypeptide from the outside world and fully protect the protein or polypeptide from inactivation;
[0006] 2) Since only one end of polyethylene glycol has an active group and can be connected with a protein or polypeptide, the efficiency is extremely low when coupling with a protein or polypeptide, and an excess of polyethylene glycol of 5 to 20 times is usually required to make the reaction full

Method used

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  • Chain-functionalized multi-level branched polyethylene glycol and synthesis method thereof
  • Chain-functionalized multi-level branched polyethylene glycol and synthesis method thereof
  • Chain-functionalized multi-level branched polyethylene glycol and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Sequential Polymerization of Ethylene Oxide, 1-Ethoxyethyl-2,3-Glycidyl Ether and Glycidol:

[0043] The ethanol (R-OH, R is CH 3 CH 2 ) and dimethyl sulfoxide (DMSO) solution of diphenylmethyl potassium (DPMK) were added to an anhydrous and oxygen-free airtight reaction kettle, and the reaction kettle was placed in an ice-water bath at 0°C, and the initiator and diphenylmethane The molar ratio of base potassium is 1:1.

[0044] Add ethylene oxide (EO) and 1-ethoxyethyl-2,3 glycidyl ether with a molar ratio of 4:1, raise the temperature to 0-50°C, and react for 24-48 hours.

[0045]

[0046] (1) Then, under the premise of not changing the airtightness of the reactor, use a peristaltic pump to slowly add glycidol (glycidol) dimethyl sulfoxide (DMSO) solution dropwise, and at the same time increase the reaction temperature to 100-120 ° C, the reaction time 4 to 12 hours.

[0047]

[0048] (2) Add ethylene oxide (EO) and 1-ethoxyethyl-2,3 glycidyl ether with a mo...

Embodiment 2

[0057] 20%R 1 for CH 2 OH, X is CH 3 Preparation of Tertiary Branched Polyethylene Glycol:

[0058] In a dry and clean 50mL round bottom flask, add 1g of the iodomethane-terminated polymer obtained in Example 1, 20mL of tetrahydrofuran and 0.5mL of concentrated hydrochloric acid, and spin dry tetrahydrofuran and concentrated hydrochloric acid after 15 minutes of reaction to obtain 20% R 1 for CH 2 OH, X is CH 3 multi-level branched polyethylene glycol. 20%R 1 for -CH 2 OH, X is CH 3 The hydrogen spectrum data of the multi-stage branched polyethylene glycol is as follows:

[0059] 1 H NMR (CDCl 3 )δ (ppm): 3.35 (CH 3 O-), 3.40-3.80 (-CH 2 CH 2 O-, glycidol).

Embodiment 3

[0061] 20%R 1 for CH 2 OCH 2 CH 2 CN, X is CH 3 Preparation of Tertiary Branched Polyethylene Glycol:

[0062] In a dry and clean 50mL round bottom flask, add 1g of 20%R prepared in Example 2 1 for CH 2 OH, X is CH 3 Multi-level branched polyethylene glycol, 20mL dioxane and 0.2g potassium hydroxide, slowly add 1mL acrylonitrile dropwise at 0°C. After continuing to react at room temperature for 8 hours, the dioxane was removed by rotary evaporation, and the product was dissolved in chloroform and washed with water three times, and the chloroform phase was dried with anhydrous magnesium sulfate, filtered, concentrated, and precipitated to obtain 20% R 1 for CH 2 OCH 2 CH 2 CN, X is CH 3 multi-level branched polyethylene glycol. 20%R 1 for CH 2 OCH 2 CH 2 CN, X is CH 3 The hydrogen spectrum data of the multi-stage branched polyethylene glycol is as follows:

[0063] 1 H NMR (CDCl 3 )δ (ppm): 2.40 (-CH 2 CN), 3.35 (CH 3 O-), 3.40-3.80 (-CH 2 CH 2 O-, glyci...

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Abstract

The invention discloses a chain-functionalized multi-level branched polyethylene glycol and a synthesis method thereof. The chain-functionalized multi-level branched polyethylene glycol has a molecular weight of 2,000-1,000,000 and has a following structural formula, wherein 1-99% of R1 independently is H; the remaining R1 independently is CH2OH, CH2OCH2CH2CN, CH2OCH2CH2CH2NH2, CH2Br, CH2N3, CH2OCH2CHO, CH2OCH2CH2COOH, CH2OCH2CH2CONH2, CH2OCH2CH=CH2, or CH2OCH2CHis equivalent to CH2, or R is an alkyl of an alcohols initiator; X is a methyl or ethyl; z is the number of X groups; n1, n2 ellipsis are respectively the degrees of polymerization of 1,2 ellipsis level branched chains and are integers from 10 to 500; the branched level is not less than 2; and the number of the branched chains on each level branch is not less than 2. Such a multi-level branched polyethylene glycol has a plurality of functionalized groups capable of being subjected to homologous protein or polypeptide coupling.The protein or polypeptide can be completely wrapped, thereby resisting the attacks of outside macromolecular matters and further reducing the inactivation of the protein or polypeptide in an organism.

Description

technical field [0001] The invention relates to a branched polyethylene glycol and a preparation method thereof, in particular to a chain functionalized multi-level branched polyethylene glycol and a synthesis method thereof. Background technique [0002] At present, in the study of biopharmaceutical carriers, the most studied is to modify the hydroxyl or carboxyl groups of linear and branched (two-arm and multi-arm) polyethylene glycols into highly reactive functional groups, such as active esters and aldehyde groups. , Amino, etc. Compared with linear polyethylene glycol with the same molecular weight, branched (two-arm and multi-arm) polyethylene glycol containing monofunctional groups has a larger molecular volume, which is more conducive to the modification and modification of small molecule drugs. At the same time, due to the special molecular shape, this branched polyethylene glycol can form an umbrella-shaped protective layer on the surface of the drug, increasing t...

Claims

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Application Information

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IPC IPC(8): C08G65/28A61K47/48
Inventor 刘超翁文桂
Owner XIAMEN SINOPEG BIOTECH
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