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Biological functionalization degradable polyester and preparation method thereof

A technology for biological functionalization and degradation of polyester, applied in organic chemistry, bulk chemical production, etc., can solve problems such as difficult high-density biological modification and unsatisfactory biocompatibility

Inactive Publication Date: 2012-07-04
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to solve the key problem that the biocompatibility of the biodegradable polyester in the prior art is not ideal and it is difficult to carry out high-density biological modification on it, by designing the synthetic route of the material and using the "click Chemistry" technology to prepare a class of biofunctionalized degradable polyesters under mild experimental conditions

Method used

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  • Biological functionalization degradable polyester and preparation method thereof
  • Biological functionalization degradable polyester and preparation method thereof
  • Biological functionalization degradable polyester and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Step (1): Add ethyl glyoxylate, bromobutyne and magnesium in toluene solvent at a molar ratio of 1:1:0.8, stir and react at 25°C for 32 hours, filter with a sand core funnel after the reaction is completed, and the organic layer Wash and extract with dichloromethane, ethyl acetate, and dilute hydrochloric acid solution in sequence, and dry the organic layer with anhydrous magnesium sulfate until it is washed with ethyl acetate / n-hexane=60 / 40 ( v / v ) as a developing agent for thin-layer chromatography separation, until the iodine gas chromogenic method shows that the reaction is complete, it is separated by silica gel chromatography column, and the organic solvent is removed by rotary evaporation to obtain a light yellow liquid.

[0053] Step (2): After the reaction in step (1) is completed, add the light yellow product obtained in step (1) in diethyl ether at a molar ratio of 1.1:1.0:0.8, 2- Bromopropionyl chloride and triethylamine were stirred at 40°C for 8 hours. ...

Embodiment 2

[0059]Step (1): Add butyl glyoxylate, propyne bromide and sodium in chloroform at a molar ratio of 1.1:1.1:0.8, stir and react at 25°C for 18 hours, filter with a sand core funnel after the reaction is complete, organic layer was extracted with toluene, dried over anhydrous magnesium sulfate until ethyl acetate / n-hexane = 70 / 30 ( v / v ) as a developing agent for thin-layer chromatography separation, until the iodine gas chromogenic method shows that the reaction is complete, it is separated by silica gel chromatography column, and the organic solvent is removed by rotary evaporation to obtain a light yellow liquid.

[0060] Step (2): After the reaction in step (1) is completed, add the light yellow product obtained in step (1), bromoacetyl chloride and pyridine in dimethylformamide at a molar ratio of 1.1:1.2:1.1, and stir at 40°C for 8h After the reaction is completed, filter with a sand core funnel, distill off the organic solvent under reduced pressure, extract with tolue...

Embodiment 3

[0066] Step (1): Add ethyl glyoxylate, chloropropane azide and Grignard reagent in chloroform at a molar ratio of 1:1.2:1.1, stir and react at 25°C for 24 hours, and use a sand core after the reaction is completed Filter through a funnel, extract the organic layer with ether, and dry over anhydrous magnesium sulfate until ethyl acetate / n-hexane = 50 / 50 ( v / v ) as a developer for thin-layer chromatography separation, until the 1,4-dinitrophenylhydrazine chromogenic method shows that the reaction is complete, it is separated by silica gel chromatography column, and the organic solvent is removed by rotary evaporation to obtain a light brown liquid.

[0067] Step (2): After the reaction in step (1) is completed, add the light brown product obtained in (1) to dimethylformamide at a molar ratio of 1.0:1.3:1.5, 2- Bromoacetyl chloride and sodium bicarbonate were stirred at 20°C for 36 hours. After the reaction was completed, filter with a sand core funnel, wash with distilled hyd...

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Abstract

The invention relates to biological functionalization degradable polyester and a preparation method thereof. The biological functionalization degradable polyester has the structural general formula shown as a formula (I) (described in the specification), wherein R1, R2 and R3 are one or more than one of hydrogen atom, alkyl, 1,2,3-triazole five-membered cyclized natural bioactive molecule; A is anatural bioactive molecule, x and y is 0 or an integral number more than 0; and n is 5-200; and the degradable polyester is prepared by virtue of 'click chemistry' reaction between biodegradable polyester containing alkynyl or azido and the natural bioactive molecule containing azido or alkynyl. The bioactive functionalization degradable polyester prepared by utilizing the 'click chemistry' in the invention has better molecule modification property and biocompatibility and has wide application prospect in the aspects of tissue engineering scaffold material, blood compatibility material, sustained or controlled release drug carrier and the like.

Description

technical field [0001] The invention relates to a medical polymer material and a preparation method thereof, in particular to synthesizing biofunctional degradable polyester based on "click chemistry" and a preparation method thereof. Background technique [0002] Existing biodegradable polyester materials, such as polylactic acid (PLA), polyglycolic acid (PGA), polyε-caprolactone (PCL) and their copolymers, have certain biodegradability, and the degradation products are non-toxic Side effects and good mechanical and processing properties have become one of the most important biomaterials in the field of biomedicine, and are widely used in tissue engineering scaffold materials, sustained and controlled release drug carriers, bone tissue repair materials and other fields; however, the existing Due to the lack of functional groups on the surface that can specifically interact with cells and proteins, and the strong hydrophobicity of biodegradable polyester, its biocompatibilit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/91C08G63/685C08B37/00C08B37/08C07D319/12
CPCY02P20/54
Inventor 罗丙红徐宠恩杨静周长忍
Owner JINAN UNIVERSITY
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