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Star-shaped polymer containing lipoyl group at the end, preparation method thereof, polymer nanoparticle prepared therefrom and application thereof

A star polymer, lipoyl technology, applied in biocompatible polymer materials, polymer nanoparticles and applications in targeted nanomedicine, star biocompatible polymer field, can solve the lack of Low toxic and side effects and high-efficiency nano-medicines, etc., to achieve excellent biodegradability, increase enrichment, and high loading efficiency

Active Publication Date: 2019-09-17
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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  • Star-shaped polymer containing lipoyl group at the end, preparation method thereof, polymer nanoparticle prepared therefrom and application thereof
  • Star-shaped polymer containing lipoyl group at the end, preparation method thereof, polymer nanoparticle prepared therefrom and application thereof
  • Star-shaped polymer containing lipoyl group at the end, preparation method thereof, polymer nanoparticle prepared therefrom and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1 Synthesis of star polymer with lipoyl group in side chain

[0056] Synthetic star polymer and linear polymer

[0057] The star polymer can be synthesized by using polyhydroxy glucose as an initiator and under the catalysis of stannous octoate to initiate the ring-opening polymerization reaction of lactide and glycolide. In N 2 Under the environment, add 0.18 g (1 mmol) polyhydroxy glucose (manufacturer: Sigma-Aldrich), 7.5 g (52 mmol) lactide and 7.5 g (65 mmol) glycolide into a closed reaction flask, and then add 4.73 Add mg of catalyst stannous octoate to the reaction flask and mix all materials evenly. Then vacuum the reaction flask-replace N 2 Three times, finally the reaction flask was evacuated for 30 minutes, and the reaction flask 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, then precipitated in ice methanol, filtered with suction and dried in vacuum to ...

Embodiment 2

[0061] Example 2 Synthesis of amphiphilic polymer PEG-PDLLA

[0062] The amphiphilic polymer PEG-PDLLA can be prepared by the ring-opening polymerization of D,L-lactide initiated by the macromolecular initiator PEG. In N 2 Under the environment, add 2.5 mL PEG ( M n =5.0 kg / mol, 0.5 g, 0.1 mmol) and D,L-lactide (0.4g, 2.8 mmol) in anhydrous toluene solution, quickly add 0.5 mL (0.2 mol / L) stannous octoate in toluene stock liquid. After reacting in a constant temperature oil bath at 110°C for 48 h, the reaction was terminated by adding glacial acetic acid. Subsequently, the product was precipitated in ice ether, filtered with suction and dried in vacuum 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 HNMR) = 8.9 kg / mol, M n (GPC) = 15.9 kg / mol, M w / M n (GPC) = 1.3.

Embodiment 3

[0063] Example 3 Synthesis of amphiphilic targeting polymer cRGD-PEG-PDLLA

[0064] The targeting polymer cRGD-PEG-PDLLA was obtained through a two-step reaction. First, synthesize maleimide functionalized amphiphilic polymer MAL-PEG-PDLLA, and then further synthesize cRGD polypeptide modified amphiphilic polymer cRGD-PEG- by Michael addition of MAL and sulfhydryl peptide cRGD-SH. PDLLA. Maleimide functionalized MAL-PEG-PDLLA is prepared by MAL-PEG-initiated ring-opening polymerization of D,L-lactide. In N 2 Under the environment, add 2.5 mL MAL-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 solution, quickly add 0.5mL (0.2 mol / L) stannous octoate in 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 then precipitated in ice ether, filtered with suction and dried in vacuum to obtain MAL-PEG-PDLLA. Then dissolve MAL-P...

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Abstract

The invention discloses a star-shaped polymer containing a lipoyl group at the end, a preparation method thereof, polymer nanoparticles prepared therefrom and applications thereof. The star-shaped polymer containing lipoyl group in the side chain is obtained by esterification. The degree of LA substitution is controllable and has excellent biocompatibility. It can be used to control the drug release system, and the prepared cancer-targeted reduction-sensitive reversible cross-linked polymer Nano-particles and nano-drugs support stable long-term circulation in the body, but are highly enriched in cancer tissues and efficiently enter cells, quickly de-crosslink and release drugs in cells, efficiently and specifically kill cancer cells, and effectively inhibit the growth of cancer without causing toxic side effects.

Description

Technical field [0001] The invention relates to a biocompatible polymer material and its application, in particular to a star-shaped biocompatible polymer containing lipoyl groups at the end, a preparation method thereof, polymer nanoparticles prepared therefrom, and a target The application to nanomedicine belongs to the field of medical materials. Background technique [0002] Polymer materials with good biocompatibility and biodegradability have been widely used in the fields of biomedicine, including tissue engineering and drug controlled release. Nanomedicine based on this has shown good application prospects, but the existing The polymer nanomedicine prepared by technology has the problems of unstable circulation in the body, low uptake by tumor cells, low intracellular drug concentration, and slow intracellular drug release speed, resulting in low drug efficacy of nanomedicine and toxic side effects caused by drug leakage. ; For example, the results of BIND-014 in clinica...

Claims

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Application Information

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