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Nano-drug based on terminal lipoyl-containing star polymer

A lipoyl star and star-shaped polymer technology, which is 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: 2018-08-14
ZHANGJIAGANG INST OF IND TECH SOOCHOW UNIV +1
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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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  • Nano-drug based on terminal lipoyl-containing star polymer
  • Nano-drug based on terminal lipoyl-containing star polymer
  • Nano-drug based on terminal lipoyl-containing star polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1 Synthesis of star-shaped polymers containing lipoyl groups in side chains

[0053] Synthesis of star and linear polymers

[0054] 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 At ambient, 0.18 g (1 mmol) of polyhydroxyglucose, 7.5 g (52 mmol) of lactide and 7.5 g (65 mmol) of glycolide were added to the closed reaction flask, followed by 4.73 mg of the catalyst stannous octoate and mix all ingredients 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 ice methanol, filtered off with suction and dried in vacuo to give a star ...

Embodiment 2

[0058] Example 2 Synthesis of amphiphilic polymer PEG-PDLLA

[0059] 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

[0060] Example 3 Synthesis of amphiphilic targeting polymer cRGD-PEG-PDLLA

[0061] 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 nano-drug based on a terminal lipoyl-containing star polymer. A side chain lipoyl-containing star polymer is obtained by esterification reaction; LA substitution degree controllability has excellent biocompatibility and can be used for controlling a drug release system; a prepared cancer-targeting reduction sensitive reversible cross-linked polymer nanoparticle nano-drugsupports an in vivo stable long cycle, is enriched in cancer tissues, efficiently enters cells, and quickly decrosslinks in the cells to release the drug; cancer cells are efficiently and specificallykilled, so that toxic or side effects caused by growth of the cancers are effectively inhibited.

Description

technical field [0001] The invention relates to a biocompatible polymer material and its application, in particular to a nano-medicine based on a star-shaped biocompatible polymer containing a lipoyl group at the end, which 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 insufficient stability of the nano drug in vivo. [0003] Cancer is a major killer that threatens human health, and its...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/51A61K47/10A61K47/69A61P35/00A61K31/337A61K31/704C08G63/91C08G63/08
CPCA61K9/5146A61K31/337A61K31/704A61K47/6935A61P35/00C08G63/08C08G63/912
Inventor 程茹王秀秀钟志远
Owner ZHANGJIAGANG INST OF IND TECH SOOCHOW UNIV
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