Preparation method of star-shaped polymer containing lipoyl at tail end and preparation method of polymer nanoparticles

A star-shaped polymer and lipoyl technology, applied in the field of medical materials, can solve the problems of lack of toxic and side effects, low-efficiency nano-medicines, etc., and achieve excellent biodegradability, prolong cycle time, and good stability.

Active Publication Date: 2019-11-22
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The emergence of nano-drugs has brought new hope for the treatment of cancer, but in the prior art, there is still a lack of high-efficiency nano-drugs that are stable in vivo circulation, cancer-specific targeting, rapid response to release drugs in cells, and less toxic and side effects. Lack of polymeric nanocarriers capable of maintaining stability and rapid intracellular drug release during in vivo circulation

Method used

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  • Preparation method of star-shaped polymer containing lipoyl at tail end and preparation method of polymer nanoparticles
  • Preparation method of star-shaped polymer containing lipoyl at tail end and preparation method of polymer nanoparticles
  • Preparation method of star-shaped polymer containing lipoyl at tail end and preparation method of polymer nanoparticles

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1 Synthesis of star-shaped polymers containing lipoyl groups in side chains

[0057] Synthesis of star and linear polymers

[0058] The star-shaped polymer can be synthesized by using polyhydroxyglucose as an initiator to initiate ring-opening polymerization of lactide and glycolide under the catalysis of stannous octoate. in N 2 Under ambient conditions, 0.18 g (1 mmol) of polyhydroxyglucose (manufacturer: Sigma-Aldrich), 7.5 g (52 mmol) of lactide and 7.5 g (65 mmol) of glycolide were added to a closed reaction bottle, followed by 4.73 mg catalyst stannous octoate was added to the reaction flask and all materials were mixed well. The reaction flask was then evacuated-displacing the N 2 Three times, and finally the reaction vial was evacuated for 30 minutes, and the reaction vial was sealed. The polymerization reaction was carried out in a vacuum box at 160° C. for 8 hours. The crude product was dissolved in dichloromethane, subsequently precipitated in i...

Embodiment 2

[0062] Example 2 Synthesis of amphiphilic polymer PEG-PDLLA

[0063] The amphiphilic polymer PEG-PDLLA can be prepared by ring-opening polymerization of D,L-lactide initiated by macroinitiator PEG. in N 2 environment, add 2.5 mL PEG (M n =5.0 kg / mol, 0.5 g, 0.1 mmol) and D,L-lactide (0.4 g, 2.8 mmol) in anhydrous toluene, quickly add 0.5 mL (0.2 mol / L) of stannous octoate toluene stock liquid. After reacting in a constant temperature oil bath at 110 °C for 48 h, glacial acetic acid was added to terminate the reaction. Subsequently, the product was precipitated in glacial ether, filtered with suction and dried in vacuo to obtain PEG-PDLLA with a yield of 88.9%. 1 H NMR (600 MHz, CDCl 3 ): δ 5.16 (-C H (CH 3 )O- ), 3.65 (-C H 2 C H 2 O-), 3.38 (C H 3 O-), 1.56 (-CH(C H 3 )O-), see figure 2 (A). M n ( 1 H NMR) = 8.9 kg / mol, M n (GPC) = 15.9 kg / mol, M w / M n (GPC) = 1.3.

Embodiment 3

[0064] Example 3 Synthesis of amphiphilic targeting polymer cRGD-PEG-PDLLA

[0065] The targeting polymer cRGD-PEG-PDLLA was obtained through a two-step reaction. First, the maleimide-functionalized amphiphilic polymer MAL-PEG-PDLLA was synthesized, and then the cRGD polypeptide-modified amphiphilic polymer cRGD-PEG- PDLLA. Maleimide-functionalized MAL-PEG-PDLLA was prepared by ring-opening polymerization of D,L-lactide initiated by MAL-PEG. in N 2 environment, add 2.5 mL MAL-PEG ( M n =5.0 kg / mol, 0.5g, 0.1 mmol) and D,L-lactide (0.4 g, 2.8 mmol) in anhydrous toluene solution, quickly add 0.5 mL (0.2 mol / L) of stannous octoate toluene stock liquid. After reacting in a constant temperature oil bath at 110 °C for 48 h, glacial acetic acid was added to terminate the reaction. The product was subsequently precipitated in glacial ether, filtered with suction and dried in vacuo to obtain MAL-PEG-PDLLA. Then MAL-PEG-PDLLA and cRGD-SH were dissolved in DMF and reacted at room...

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Abstract

The invention discloses a preparation method of a star-shaped polymer containing lipoyl at the tail end and a preparation method of polymer nanoparticles. The star-shaped polymer with the side chain containing lipoyl is obtained through esterification reaction, has controllable LA substitution degree , excellent biocompatibility, and can be used for controlling a drug release system by using the star-shaped polymer; the prepared cancer-targeted reduction-sensitive reversibly-crosslinked polymer nanoparticle nano-drug can be in in-vivo stable long circulation, is highly enriched in cancer tissues, efficiently enters cells, is rapidly decrosslinked in the cells, releases the drug, to efficiently and specifically kill cancer cells, thus effectively inhibiting the growth of cancer and having no toxic or side effect.

Description

[0001] The present invention is a star-shaped polymer with a lipoyl group at the end of the invention, its preparation method, polymer nanoparticles prepared therefrom and its application. The application date is March 1, 2018, and the application number is 201810172208X. Case application, which belongs to the part of product preparation method. technical field [0002] The invention relates to a biocompatible polymer material and its application, in particular to a star-shaped biocompatible polymer containing a lipoyl group at the end, a preparation method thereof, a polymer nanoparticle prepared therefrom, and a target biocompatible polymer. The application to nano medicine belongs to the field of medical materials. Background technique [0003] Polymer materials with good biocompatibility and biodegradability have been widely used in biomedical fields, including tissue engineering and drug controlled release. The polymer nanomedicine prepared by the technology has the pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/91C08G63/08A61K9/51A61K47/34A61K31/337A61K31/704A61P35/00
CPCA61K9/5146A61K31/337A61K31/704A61P35/00C08G63/08C08G63/912
Inventor 程茹王秀秀钟志远
Owner SUZHOU UNIV
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