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Mono-methoxy polyethylene glycol derivatives and their preparing process and use

A technology of polyethylene glycol silane and monomethoxy, which is applied in biological testing, silicon organic compounds, chemical instruments and methods, etc., can solve the problems of complex processing process and weak inhibitory effect, and achieve simple processing process and inhibitory effect. Effect of non-specific adsorption and mild use conditions

Inactive Publication Date: 2005-11-02
INST OF PROCESS ENG CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to overcome the existing adsorption inhibitors to inhibit the non-specific adsorption of biomolecules on the surface of the material, the inhibitory effect is not strong, the processing process is complicated and other defects, thereby providing a kind of inhibition of the non-specific adsorption of biomolecules on the surface of the material Monomethoxypolyethylene glycol silane derivative with obvious effect and simple and convenient treatment process, its preparation method and use

Method used

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  • Mono-methoxy polyethylene glycol derivatives and their preparing process and use
  • Mono-methoxy polyethylene glycol derivatives and their preparing process and use

Examples

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Effect test

Embodiment 1

[0030] Embodiment 1, preparation monomethoxy polyethylene glycol silane derivative 1

[0031] Dissolve monomethoxytriethylene glycol (CH 3 O(CH 2 CH 2 O) 3 H) 6.560 g (40 mmol) and 4.444 g (44 mmol) of triethylamine, cooled in an ice-salt bath. Another 8.426g (44mmol) of p-toluenesulfonyl chloride was dissolved in 50ml of dichloromethane. Under electromagnetic stirring, the p-toluenesulfonyl chloride-dichloromethane solution was added dropwise to the reaction solution. Afterwards, the ice-salt bath was removed, returned to room temperature, and continued to stir for 24 hours. Filtration, the filtrate was concentrated by rotary evaporation, and then petroleum ether: ethyl acetate = 1:1 was used as the eluent, and silica gel column chromatography was used to separate to obtain 9.540 g (30 mmol) of monomethoxytriethylene glycol p-toluenesulfonate. Yield 75%.

[0032] 897 mg (39 mmol) of sodium metal was dissolved in 6 ml of methanol to obtain 39 mmol of sodium methoxide. ...

Embodiment 2

[0033] Embodiment 2, preparation monomethoxy polyethylene glycol silane derivative 2

[0034] The same method as in Example 1 was used.

[0035] Dissolve 1.748g (23mmol) monomethoxyethylene glycol (CH 3 OCH 2 CH 2 OH) and 2.362g (30mmol) of pyridine, cooled in an ice-salt bath. Another 5.745g (30mmol) of p-toluenesulfonyl chloride was dissolved in 50ml of dichloromethane. Under electromagnetic stirring, the p-toluenesulfonyl chloride-dichloromethane solution was added dropwise to the reaction solution. After that, the ice-salt bath was removed, returned to room temperature, and stirred for 24 hours. Filtration, the filtrate was concentrated by rotary evaporation, and then using petroleum ether: ethyl acetate = 1:1 as eluent, silica gel column chromatography to obtain 3.45g (15mmol) monomethoxyethylene glycol p-toluenesulfonate, Yield 65.2%.

[0036]345 mg (15 mmol) of sodium metal was dissolved in 4 ml of methanol to obtain 15 mmol of sodium methoxide. After that, 2.7 ...

Embodiment 3

[0037] Embodiment 3, preparation monomethoxy polyethylene glycol silane derivative 3

[0038] The same method as in Example 1 was used.

[0039] Dissolve 1.92g (5mmol) monomethoxy octaethylene glycol (CH 3 O(CH 2 CH 2 O) 8 H) and 5.925g (7.5mmol) of pyridine, cooled in an ice-salt bath. Another 1.436g (7.5mmol) p-toluenesulfonyl chloride was dissolved in 50ml of dichloromethane. Under electromagnetic stirring, the p-toluenesulfonyl chloride-dichloromethane solution was added dropwise to the reaction solution. Afterwards, the ice-salt bath was removed, returned to room temperature, and continued to stir for 24 hours. Filtration, the filtrate was concentrated by rotary evaporation, and then petroleum ether: ethyl acetate = 1:1 was used as the eluent, separated by silica gel column chromatography to obtain 1.668 g (3.1 mmol) of monomethoxy octaethylene glycol p-toluenesulfonate , yield 62%.

[0040] 78 mg (3.4 mmol) of sodium metal was dissolved in 4 ml of ethanol to obta...

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Abstract

The invention relates to a monomethoxy carbowax silane derivant, the method and usage for it. The structural formula ó±of such alkoxy silane carbowax derivant is (R1O)zR2(3-z)Si(CH2)nA(CH2CH2O)mCH3, wherein R1ú¼R2 represent separately linear or branched chain alkane with 1-10 carbon atoms, aralkyl or aryl radicals; A means oxygen atom or sulfur atom; z equals to 1, 2 or 3; while n is an integral between 1 and 12; m also is an integral between 1 and 15. Such a derivant can be produced by reacting monomethoxy carbowax with organic amine and p-toluene sulfonyl chloride to get monomethoxy carbowax ethyl p-toluenesulfonate; then with alkoxy silane compound and sodium alcoholate to obtain the derivant of the invention. Such derivant can be used as an absorb depressant to block non-specific absorption of biomolecule on the surface of inorganic material, with gentle condition and simple process.

Description

technical field [0001] The invention relates to a monomethoxy polyethylene glycol silane derivative, a preparation method and application thereof. Background technique [0002] Nonspecific adsorption of proteins and other biomolecules on material surfaces is a common problem for biomedical instruments, biochemical processes, and biodiagnostics, especially when metal or glass materials are involved, because proteins and other biomolecules are Adsorption forms a multilayer film on the surface of these substances. Current methods to inhibit this adsorption are the use of adsorption inhibitors - long-chain silanes or polyethylene glycols. The former forms a long-chain alkyl molecular film on the surface through the covalent interaction between long-chain silane and glass or metal surface oxides, which masks the electrostatic interaction between the substrate material and biomolecules, thereby inhibiting the physical adsorption between the two. . However, the surface free ener...

Claims

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Application Information

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IPC IPC(8): C07F7/02
Inventor 曾冬冬张冬海陈运法
Owner INST OF PROCESS ENG CHINESE ACAD OF SCI
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