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Biological functionalization degradable polyester and preparation method thereof

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

Inactive Publication Date: 2013-09-04
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] like figure 1 As shown, 1756cm -1 The characteristic infrared absorption peak of ester carbonyl is at 3289cm -1 and 2123 cm -1 The characteristic infrared absorption peak of the alkynyl group is at the place, and the results show that the steps (1) and (2) synthesized the alkynylated lactide derivative monomer.

[0053] Step (3): Weigh 12 g of the alkynylated glycolide derivative crystal obtained in step (2), and add 0.5 w The stannous octoate of t% is polymerized under the assistance of microwave, wherein: setting reaction temperature is 100 ℃, and microwave power is 30W, and reaction time is 20min; Solid crude product is dissolved with chloroform, dehydrated alcohol precipitation, then in 45 °C for 24 hours in vacuum to obtain a side chain alkynylated biodegradable polyester (yield: 93.5%, number average molecular weight: 1.08*10 4 ).

[0054] Step (4): Weigh side-chain alkynylated biodegradable polyester (10.8g, 1.0mmol) and azide cholesterol (6.2g, 15.0mmol) i...

Embodiment 2

[0059] Step (3): Weigh 6 g of alkynylated glycolide derivative crystals obtained in step (2) and 9 g of lactide, and add 0.5 w t% of 4-dimethylaminopyridine, polymerized under microwave assistance, wherein: set the reaction temperature to 40°C, the microwave power to 50W, and the reaction time to 35min; the solid crude product was dissolved in chloroform and precipitated in absolute ethanol , and then vacuum-dried at 45°C for 24 hours to obtain a side chain alkynylated biodegradable copolyester (yield: 94.3%, number average molecular weight: 3.17*10 4 ).

[0060] like figure 2 As shown, 1757cm -1 The characteristic infrared absorption peak of ester carbonyl is at 3290cm -1 and 2120 cm -1 The place is the characteristic infrared absorption peak of the alkynyl group; image 3 The chemical shifts at 1.4 and 1.6 are the proton resonance peaks of the methyl group on the lactyl unit in the terminal and the chain segment respectively, 4.4 and 5.2 are the proton resonance peaks ...

Embodiment 3

[0066] Step (3): Weigh 3 g of azide glycolide derivative crystals obtained in step (2) and 9 g of caprolactone, and add 1.0 w t% of stannous octoate was polymerized by the bulk sealing tube method, wherein: the reaction temperature was set at 100°C, and the reaction time was 24h; the solid crude product was dissolved in chloroform, precipitated with anhydrous methanol, and then vacuum-dried at 40°C for 36h , to obtain a side chain azide biodegradable copolyester (yield: 93.6%, number average molecular weight: 2.98*10 4 ).

[0067] Step (4): Weigh side chain azide biodegradable copolyester (2.98g, 0.1 mmol) and alkynylated chitohexaose (1.5g, 1.5 mmol) into a 50ml three-neck flask, add 30ml of di Methyl sulfoxide was used to completely dissolve the raw materials, and copper bromide (CuBr, 21.6 mg, 0.15 mmol) and pentamethyldivinyltriamine (PMEDTA, 30 μL, 0.15 mmol) were added under nitrogen protection, and reacted at 25 °C for 36 h . After the reaction, the polymerization sy...

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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 a natural 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 Patents(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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