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Polycaprolactone/amylose amphiphilic block polymer as well as preparation method and use thereof

A technology of polycaprolactone and amylose, applied in the field of polycaprolactone/amylose amphiphilic block polymer and its preparation, can solve toxic side effects, non-biodegradability, and lack of reaction of molecular chains To achieve the effect of strong function, good biodegradability and biocompatibility, and abundant sources

Inactive Publication Date: 2008-07-30
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the hydrophilic PEG segment used also has some disadvantages: first, it does not have biodegradability, and only PEG with low molecular weight can be phagocytized by cells or excreted through the kidney filter membrane. If it is used as a drug carrier material Long-term effects on the human body are very likely to produce toxic and side effects; second, the molecular chain still lacks reactive groups, which is not conducive to the subsequent modification of the formed block polymer micelles or the targeted control of drug-loaded micelles freed

Method used

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  • Polycaprolactone/amylose amphiphilic block polymer as well as preparation method and use thereof
  • Polycaprolactone/amylose amphiphilic block polymer as well as preparation method and use thereof
  • Polycaprolactone/amylose amphiphilic block polymer as well as preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) Weigh myristyl alcohol, Sn(Oct) according to the ratio of substances 1:0.0055:55 2 , ε-CL in a polymerization tube, after repeated vacuuming / argon filling for 3 times, heat-seal the tube under vacuum state, and then place the polymerization tube in an oil bath at 130°C for 7 hours to react. After the reaction, dissolve with tetrahydrofuran to obtain a polymer solution, and use ether (10 times the volume of tetrahydrofuran) to precipitate the product hydroxyl-terminated polycaprolactone PCL-OH, which is filtered and dried under reduced pressure for future use. Yield: 90%.1 HNMR (in d 6 -DMSO, 300MHz) δppm: 1.40, 1.66, 2.33, 4.07 (CH 2 ); 0.89 (CH 3 ); 3.7 (CH 2 OH). through 1 HNMR analysis shows that the number average molecular weight of PCL-OH is 5914.

[0035] Dissolve 0.2mmol of PCL-OH and 0.4mmol of p-aldehyde benzoic acid in 20ml of tetrahydrofuran, add 10ml of tetrahydrofuran solution dissolved with 0.4mmol of DCC and 20mg of DMAP under stirring, and the...

Embodiment 2

[0039] (1) Weigh myristyl alcohol, Sn(Oct) according to the ratio of substances 1:0.008:80 2 , ε-caprolactone in a polymer tube, after repeated vacuuming / argon filling for 3 times, heat-seal the tube under vacuum, and then place the polymer tube in an oil bath at 130°C for 7 hours to react. After the reaction, the polymer solution was obtained by dissolving in tetrahydrofuran, and the product PCL-OH was precipitated with diethyl ether (11 times the volume of tetrahydrofuran), filtered, and dried under reduced pressure for future use. Yield: 91%. 1 HNMR (in d 6 -DMSO, 300MHz) δppm: 1.40, 1.66, 2.33, 4.07 (CH 2 ); 0.89 (CH 3 ); 3.7 (CH 2 OH). through 1 HNMR analysis showed that the number average molecular weight of PCL-OH was 8764.

[0040] Dissolve 0.2mmol of PCL-OH and 0.4mmol of p-aldehyde benzoic acid in 20ml of tetrahydrofuran, add 10ml of tetrahydrofuran solution dissolved with 0.4mmol of DCC and 20mg of DMAP under stirring, and then seal the reaction at room tempe...

Embodiment 3

[0044] (1) Weigh myristyl alcohol, Sn(Oct) according to the ratio of substances 1:0.009:45 2 , ε-caprolactone (ε-CL) in a polymerization tube, after repeated vacuuming / argon filling for 3 times, heat-seal the tube in a vacuum state, and then place the polymerization tube in an oil bath at 120°C React for 8 hours. After the reaction, the polymer solution was obtained by dissolving in tetrahydrofuran, and the product PCL-OH was precipitated with diethyl ether (12 times the volume of tetrahydrofuran), filtered, and dried under reduced pressure for future use. The number average molecular weight of the obtained PCL-OH was 5014.

[0045] Dissolve 0.2mmol of PCL-OH and 0.3mmol of p-aldehyde benzoic acid in 25ml of tetrahydrofuran, add 10ml of tetrahydrofuran solution dissolved with 0.3mmol of DCC and 14.6mg of DMAP under stirring, and then seal the reaction at room temperature for 1 day. After the reaction was completed, the resulting dicyclohexyl urea (DCU) precipitate was filter...

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Abstract

The invention discloses a polycaprolactone / amylase amphiphilic block polymer. The preparation method thereof adopts the steps that: firstly, hydroxyl at the terminal of terminal hydroxyl polycaprolactone has esterification reaction with terephthalaldehydic acid to generate terminal aldehyde polycaprolactone, then hemiacetal hydroxyl at the reducing terminal of amylase has reduction and amination reaction with excess hexanediamine under the catalysis of sodium cyanoboronhydride to generate terminal amido amylase, and finally, polycaprolactone / amylase amphiphilic block polymer is obtained through coupling reaction between terminal aldehyde polycaprolactone and terminal amido amylase under the catalysis of sodium cyanoboronhydride. The polycaprolactone / amylase amphiphilic block polymer of the invention can form micelle in water, and also form reversed micelle in an organic solvent. The polycaprolactone / amylase amphiphilic block polymer of the invention not only has the capability of forming micelle in water or the organic solvent, but also has the advantages of good performance, strong functions, and broad application range, thereby having potential application value in the biological medicine field.

Description

technical field [0001] The invention belongs to the field of functional polymer materials, in particular to a polycaprolactone / amylose amphiphilic block polymer and its preparation method and application. Background technique [0002] Polycaprolactone (PCL) is an important class of aliphatic polyesters. It has the advantages of non-toxicity, good biocompatibility and biodegradability. It has been widely used in the production of biomedical materials, especially drug controlled release carriers. Material. However, a single PCL material is extremely hydrophobic, not hydrophilic, and its chemical structure lacks reactive functional groups, which greatly limits its application in the field of biomedicine. Therefore, it is urgent to modify its structure or modified. [0003] So far, the most reported method is to use hydrophilic polyethylene glycol (PEG) molecular chains and PCL molecular chains to form amphiphilic block polymers. Chinese invention patents CN 1425706A and CN171...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G81/00C08G63/91C08B31/00C08J3/05A61K47/36
Inventor 李本刚张黎明
Owner SUN YAT SEN UNIV
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