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Construction and application of core-shell type intelligent nano delivery system

A technology of chondroitin sulfate and chlorin, which is applied in the synthesis of chondroitin sulfate-chlorin amphiphilic polymer, the application field of core-shell type cross-linked self-assembled nano drug delivery system combined with ultrasonic therapy for anti-tumor , can solve the problem of less application, and achieve the effect of improving aggregation, inducing cell apoptosis, and cheap and easy-to-obtain raw materials

Active Publication Date: 2020-02-18
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the application of lipoic acid as a synthetic amphiphilic polymer for this purpose is less

Method used

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  • Construction and application of core-shell type intelligent nano delivery system
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  • Construction and application of core-shell type intelligent nano delivery system

Examples

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preparation example Construction

[0052] In another embodiment of the present invention, the preparation method of the chondroitin sulfate-chlorin e6 amphoteric polymer modified by lipoic acid is provided, and the steps of the preparation method are as follows:

[0053] (1) Synthesis of chondroitin sulfate-adipate dihydrazide: Dissolve chondroitin sulfate in distilled water, add adipate dihydrazide, 1-(3-dimethylaminopropyl) -3-Ethylcarbodiimide hydrochloride, N-hydroxysuccinimide, adjust the pH of the reaction system to 6-7 with sodium hydroxide, and stir at room temperature for 20-30 hours to obtain chondroitin sulfate-adipic acid Dihydrazide;

[0054] (2) Activation of chlorin e6: Dissolve chlorin e6 in N,N-dimethylformamide, and sequentially add 1-(3-dimethylaminopropyl)-3-ethyl carbon Diimine hydrochloride, N-hydroxysuccinimide, activated at room temperature for 5-8 hours, then dropwise adding an organic base to adjust the pH of the solution to 7-9;

[0055] (3) Synthesis of chondroitin sulfate-chlorin ...

Embodiment 1

[0074] Example 1: Synthesis of lipoic acid-modified chondroitin sulfate-chlorin e6 polymer

[0075] (1) Synthesis of chondroitin sulfate-adipate dihydrazide: Weigh 0.5g chondroitin sulfate and dissolve it in 150mL distilled water, stir to make it fully swell and dissolve, then add 5.0g adipic acid dihydrazide to the solution in turn Hydrazide, 1.6g 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.23g N-hydroxysuccinimide, adjust the pH value of the reaction system to 6.8 with sodium hydroxide , reacted at room temperature for 24 hours, dialyzed with distilled water for three days, and freeze-dried to obtain the intermediate product chondroitin sulfate-adipate dihydrazide.

[0076] (2) Weigh 12 mg of chlorin e6 and dissolve it in 4 mL of N,N-dimethylformamide, and sequentially add 1-(3-dimethylaminopropyl )-3-ethylcarbodiimide hydrochloride, N-hydroxysuccinimide equivalent to 2 times the molar amount of chlorin e6, stirred at room temperature for 30 minutes, a...

Embodiment 2

[0078] Embodiment 2: the synthesis of chondroitin sulfate-chlorin e6 polymer

[0079] (1) Synthesis of chondroitin sulfate-adipate dihydrazide: Weigh: 0.5g chondroitin sulfate is dissolved in 150mL distilled water, stir to make it fully swell and dissolve, then add 5.0g adipic acid to the solution successively Dihydrazide, 1g 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.1g N-hydroxysuccinimide, adjust the pH value of the reaction system to 6.6 with sodium hydroxide , reacted at room temperature for 24 hours, dialyzed with distilled water for three days, and freeze-dried to obtain the intermediate product chondroitin sulfate-adipate dihydrazide.

[0080] (2) Weigh 24 mg of chlorin e6 and dissolve it in 3 mL of N,N-dimethylformamide, and sequentially add 1-(3-dimethylaminopropyl )-3-ethylcarbodiimide hydrochloride, N-hydroxysuccinimide equivalent to 2 times the molar amount of chlorin e6, stirred at room temperature for 30 minutes, and then added 2 times th...

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Abstract

The invention discloses a lipoic acid modified chondroitin sulfate-chlorin e6 amphoteric polymer. According to the polymer, chondroitin sulfate is used as a water-soluble framework material, chlorin e6 serves as a hydrophobic modifier to be connected into a chondroitin sulfate framework, lipoic acid is used as an interface cross-linking agent to conduct surface modification on a chondroitin sulfate-chlorin e6 polymer, and the polymer further has a hydrophobic core to be capable of entrapping an insoluble anti-tumor drug. The lipoic acid modified chondroitin sulfate-chlorin e6 amphoteric polymer prepared by the invention is used as a drug carrier to prepare reversible cross-linked nano-micelles, and thus rapid decrosslinking in tumor cells can be realized; and as an excellent nano-carrier,sonodynamic therapy (SDT) of the tumors is achieved, and the lipoic acid modified chondroitin sulfate-chlorin e6 amphoteric polymer has the effects of increasing the level of active oxygen in the cells, promoting tumor cell apoptosis and remarkably inhibiting tumor cell growth. Meanwhile, the hydrophobic core provides entrapment of the anti-tumor drug, combined application of chemotherapy and SDTof the tumors can be achieved, and the anti-tumor effect is expected to be improved.

Description

technical field [0001] The invention belongs to the field of biomedical materials and nano drug preparations, in particular to the synthesis of a lipoic acid-modified chondroitin sulfate-chlorin amphiphilic polymer, and its use as a core-shell type cross-linked self-assembled nano drug delivery system Anti-tumor application combined with ultrasound therapy. Background technique [0002] As a disease that threatens human health, cancer has the characteristics of high mortality and poor prognosis. Chemotherapeutic drugs are one of the main means of tumor treatment, but most of them have high cytotoxicity and lack of selective killing of tumor tissues, and are likely to cause toxic side effects to normal tissues, which has become the main obstacle to limit the efficacy of chemotherapy. In the 1980s, nanoscience technology, as a rising new technology, was applied to the construction of precisely targeted nano-drug delivery systems. In order to improve drug efficacy, the combina...

Claims

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Application Information

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IPC IPC(8): A61K9/107A61K47/36A61K47/22A61K31/337A61K41/00A61P35/00
CPCA61K9/1075A61K31/337A61K41/0028A61K47/22A61K47/36A61P35/00
Inventor 翟光喜刘梦锐赵小刚
Owner SHANDONG UNIV
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