Polymerizable monomers and process of preparation thereof

A technology for polymerizing monomers and monomers, applied in the field of polymerizable monomers, to achieve the effects of easy preparation, no microbial contamination, and stable microbial contamination

Inactive Publication Date: 2006-08-23
COUNCIL OF SCI & IND RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the application of this method is limited by the extremely low temperature and stringent polymerization conditions required

Method used

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  • Polymerizable monomers and process of preparation thereof
  • Polymerizable monomers and process of preparation thereof
  • Polymerizable monomers and process of preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Preparation of acryloyl N-acetylglucosamine (Ac.NAG)

[0085] 11.1 gm N-acetylglucosamine and 4.2 gm sodium bicarbonate were dissolved in a beaker equipped with a dropping funnel and pH meter. The resulting clear solution was continuously stirred at 5°C on a magnetic stirrer. 5 ml of acryloyl chloride dissolved in 5 ml of dichloromethane was added dropwise.

[0086] The reaction mixture was maintained at pH 7.5 by adding a saturated solution of sodium bicarbonate. After adding acryloyl chloride, unreacted acryloyl chloride was extracted into 100 ml ethyl acetate. The clear aqueous solution was separated and acidified to pH 5.0 by addition of concentrated hydrochloric acid. Finally the acryloyl N-acetylglucosamine is precipitated in distilled acetone. The product was reprecipitated in acetone.

Embodiment 2

[0088] Preparation of methacryloyl 6-aminocaproic acid (M.Ac.6-ACA)

[0089] A dropping funnel and a pH meter were assembled on a 250ml capacity beaker. 13.16 gm of 6-ACA, 4 gm of sodium hydroxide and 80 ml of water were continuously stirred at 5°C on a magnetic stirrer. To the above solution was added dropwise 9 ml of methacryloyl chloride dissolved in 10 ml of dichloromethane (dichlorQmeJhane). The pH of the reaction mixture was maintained at 7.5 by addition of 10M NaOH solution. Unreacted acid chloride was extracted with 100 ml of ethyl acetate. The clear aqueous solution was acidified to pH 5.0 using concentrated hydrochloric acid and the product was extracted into ethyl acetate (3 x 100ml). The resulting organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. The viscous liquid was added into 500ml petroleum ether to obtain the solid phase product, which was dried in vacuum for 48 hours.

Embodiment 3

[0091] Preparation of acryloyl 6-aminocaproic acid N-acetylglucosamine (Ac.6-ACA.NAG)

[0092] 5 gm of acryloyl 6-aminocaproic acid (Ac.6-ACA) and 5.97 gm of N-acetylglucosamine were dissolved in 20 ml of dry dimethylformamide (DMF). A clear solution was obtained by continuous stirring and addition of 5.57 gm of dicyclohexylcarbodiimide (DCC) as coupling agent. Stirring of the reaction mixture was continued at room temperature for 24 hours. Dicyclohexyl urea (DCU) was filtered off and the monomer containing the spacer and ligand NAG was precipitated in distilled acetone. Vacuum dried for 48 hours.

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Abstract

The present invention relates to polymerizable monomers for applications in medicine and biotechnology and synthesis thereof. The polymerizable ligands containing nacetyl glucosamine bind more strongly to lysozyme than nag itself. The binding is further enhanced when a spacer arm, for example 6- amino caproic acid (6-aca) is introduced in the structure. The conjugated ligands could be used for prevention and treatment of bacterial and viral infections. Moreover these ligands can be coupled to stimuli sensitive polymers and used for the recovery of biomolecules. The methodology can be extended to other ligands such as sialic acid and the corresponding polymers used for preventing influenza and for rotavirus infections.

Description

field of invention [0001] The present invention relates to a polymerizable monomer containing N-acetylglucosamine (NAG) of the following general formula (1), [0002] [0003] Among them, R is H, CH 3 、C 2 h 5 、C 6 h 5 ;X is based on 4-aminobutyric acid (4-ABA), 6-aminocaproic acid (6-ACA), 8-aminooctanoic acid (8-AOA), 10-aminodecanoic acid (10-ADA), 11-aminodecanoic acid Monoalkanoic acid (11-ADA); Y is selected from N-acetylglucosamine, mannose, galactose and sialic acid, fructose, ribulose, erythrolose (erythrolose), xylulose, psicose, Sorbose, tagatose, glucopyranose, fructofuranose, deoxyribose, galactosamine, sucrose, lactose, isomaltose, maltose, cellobiose, cellulose and amylose. [0004] More particularly, the invention relates to said monomers containing carbohydrate ligands and methods of making them by the specific linkages described herein. In particular, the present invention relates to monomers that bind to lysozyme much more strongly than NAG itself....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/04C07H13/06
CPCC07H13/04C07H13/06
Inventor 莫汉·戈帕克里希纳·库尔卡尼贾扬特·贾甘纳特·砍杜达尔
Owner COUNCIL OF SCI & IND RES
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