Multi-arm star-shaped polyethylene glycol containing single-activity functional groups and preparation method thereof

A polyethylene glycol and functional group technology, applied in the field of multi-arm star polyethylene glycol and its preparation, can solve problems such as inability to carry out specific reactions, and achieve simple preparation method, good application value and industrial prospect, high yield effect

Inactive Publication Date: 2010-09-15
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the end groups of each arm in these multi-armed PEOs often contain the same hydroxyl functional group, which cannot react specifically

Method used

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  • Multi-arm star-shaped polyethylene glycol containing single-activity functional groups and preparation method thereof
  • Multi-arm star-shaped polyethylene glycol containing single-activity functional groups and preparation method thereof
  • Multi-arm star-shaped polyethylene glycol containing single-activity functional groups and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Preparation of small molecular compounds containing three active hydroxyl groups and one protected hydroxyl group

[0039] Under a nitrogen atmosphere, add 20 g of 2,2-iminobisethanol and 150 ml of THF to a 250 ml dry and clean round-bottom flask successively, and slowly dissolve 28 g of 1-ethoxyethyl 2 through a dropping funnel at room temperature, 3-Glycidyl ether was added, and the dropwise addition was completed within about 2.0 hours. After continuing to stir the reaction for 24 hours, the THF solvent was removed by rotary evaporation at 45°C. It was extracted and separated with ether and water, and the purity of the product was checked by thin-layer chromatography. Finally, a viscous colorless transparent liquid was obtained, which was sealed and stored for future use.

[0040]

[0041] 1 H NMR (CD 3 OD)d(ppm): 1.2(m, CH 3 CH 2 O-), 1.3 (m, CH 3 -CH-), 2.5-2.8(m, 6H(-CH 2 ) 2 -N-CH 2 -), 3.5-3.65 (m-CH 2 -), 3.8(m(-CH 2 ) 2 CH-OH), 4.7(m, -OCH(CH 3...

Embodiment 2

[0042] The preparation of the three-arm star-shaped polyethylene glycol (B 3 )

[0043] Add 0.50g of the above-mentioned small molecular compound, 30ml DMSO, 30ml THF, 2.8ml DPMK, and 10ml ethylene oxide into a dry and clean 300ml ampoule with a stirring magnet in sequence, and react at 40°C for 48h. Then, continue to add excess DPMK, stir well and then add bromoethane which is twice the molar amount of DPMK, and continue to react at 40°C for 24h. After the reaction, concentrate the polymer, add 100ml of methanol solvent to dissolve, then add 9ml of concentrated hydrochloric acid for hydrolysis reaction; react at room temperature for 3.0h, then spin off the solvent and extract with a large amount of dichloromethane, and then concentrate the organic layer after removing water , and finally precipitated with a large amount of anhydrous ether, filtered, and vacuum-dried to obtain a three-armed star-shaped polyethylene glycol containing an active hydroxyl group at the link.

[0...

Embodiment 3

[0046] Embodiment 3 The fourth arm end group is the preparation of the multi-arm star polyethylene glycol of hydroxyl group (AB 3 )

[0047] Dissolve 7.0 g of the three-arm star-shaped polyethylene glycol containing an active hydroxyl group at the above-mentioned link in 60 ml of DMSO and 60 ml of THF mixed solvent system, and transfer it to a dry and clean 500 ml ampoule with a stirring bar, and then slowly Add 3.5ml DPMK. Finally, 10ml of ethylene oxide was added, and the temperature was raised to 50°C for 48h. After the reaction was finished, the reaction was terminated with methanol, and the crude product was precipitated with anhydrous ether, filtered, and vacuum-dried to obtain the multi-armed star-shaped polyethylene glycol (AB 3 ).

[0048]

[0049] 1 H NMR (CD 3 OD)d(ppm): 1.13(m, CH 3 CH 2 O-), 2.5-2.8 (m, (-CH 2 ) 2 -N-CH 2 -), 3.51-3.77 (m, -CH 2 CH 2 O-of PEO).

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Abstract

The invention belongs to the synthetic chemistry field of macromolecules and relates to multi-arm star-shaped polyethylene glycol containing single-activity functional groups and a preparation method thereof. The preparation method comprises the following steps of: firstly, preparing a molecular compound containing n active hydroxyls and one protected hydroxyl; initiating ethylene oxides to carry out ring-opening polymerization by using the n active hydroxyls on the compound and diphenylmethyl potassium as common initiation systems, and then sealing ends by using bromoethane to obtain n-arm star-shaped polyethylene glycol; eliminating protection groups of the protected hydroxyl in a joint from an acid environment to obtain n-arm star-shaped polyethylene glycol containing one active hydroxyl; initiating ring-opening polymerization for the second time by using the active hydroxyl and the diphenylmethyl potassium as common initiation systems to obtain the multi-arm star-shaped polyethylene glycol (ABn); and finally, selectively modifying the functional groups of the hydroxyl at the tail ends of the n+1 arm to prepare the multi-arm star-shaped polyethylene glycol containing single-activity functional groups.

Description

technical field [0001] The invention belongs to the field of polymer synthesis chemistry, and in particular relates to a multi-arm star-shaped polyethylene glycol (ABG) containing a single active functional group. n ) and its preparation method. Background technique [0002] In the study of biopharmaceutical carrier materials, the modification of single-terminal hydroxyl polyethylene glycol (mPEO) or double-terminal hydroxyl polyethylene glycol end groups is converted into highly reactive functional groups, such as succinimide succinate, aldehyde Base, hydrazide, etc. are currently the most researched materials. According to literature reports (Biomaterials, 2001, 22, 405-417), in the process of coupling with protein drugs such as interferon α-2A, two-arm PEO will have a better effect than linear PEO, that is, single-arm PEO, and this PEO-like are often prepared by coupling methods. [0003] In 1995, Monfardini et al. coupled mPEO to the two amino groups of lysine to obta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/28C08G65/331
Inventor 王国伟张衍楠黄骏廉
Owner FUDAN UNIV
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