Star polymer with terminal containing lipoyl, preparation method thereof, polymer nanoparticles prepared from star polymer, and applications of star polymer

A star-shaped polymer, lipoyl technology, used in star-shaped biocompatible polymers, polymer nanoparticles and applications in targeted nano-drugs, biocompatible polymer materials, can solve the lack of Toxic and side effects are small and high-efficiency nano-drugs, etc., to achieve excellent biodegradability, prolong cycle time, and improve bioavailability.

Active Publication Date: 2018-09-28
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 polymer with terminal containing lipoyl, preparation method thereof, polymer nanoparticles prepared from star polymer, and applications of star polymer
  • Star polymer with terminal containing lipoyl, preparation method thereof, polymer nanoparticles prepared from star polymer, and applications of star polymer
  • Star polymer with terminal containing lipoyl, preparation method thereof, polymer nanoparticles prepared from star polymer, and applications of star polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1 Synthesis of star-shaped polymers containing lipoyl groups in side chains

[0056] Synthesis of star and linear polymers

[0057] 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

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

[0062] 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

[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, 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 star polymer with a terminal containing lipoyl, a preparation method thereof, polymer nanoparticles prepared from the star polymer, and applications of the star polymer. Thestar polymer with side chains containing lipoyl is prepared through esterification reaction; the LA substitution degree is controllable; excellent biocompatibility is achieved; the star polymer is used for controlling drug release systems; the reduction sensitive reversibly crosslinked polymer nanoparticle nanometer medicine which is prepared from the star polymer and possesses cancer targeting performance is used for supporting in vivo stable long cycle; enrichment in cancer tissues is realized; high efficiency entering into cells is realized; rapid de-crosslinking in cells is realized; release of drugs is realized; high efficiency killing of cancer cells with specificity is realized; growth of cancer is inhibited effectively without causing toxic or side effect.

Description

technical field [0001] 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 [0002] 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 problems of unstable circulation in the body, low tumor cell uptake, low intracellular drug concentration, and slow intracellular drug release rate, resulting in low efficacy of nanomedicine and toxic side effects caused by drug leakage. ; For example, the results of BIND-014 in the second clinical phase did not meet expectations, due to the insuffic...

Claims

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Application Information

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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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