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Redox responsive amphiphilic copolymer as well as preparation method and application thereof

An amphiphilic copolymer and a responsive technology, which can be used in drug combinations, pharmaceutical formulations, organic active ingredients, etc., can solve the problems of limited tumor treatment effect and inability to meet the needs of use, and achieve simple preparation methods and good stability Effect

Active Publication Date: 2017-08-04
SHANGHAI UNIV OF T C M
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned copolymers have limited therapeutic effects on tumors and cannot meet the needs of use.
[0009] At present, there is no report on the use of hydrophobic anticancer drugs as hydrophobic blocks to modify hyperbranched polyamidoamines to form a polymer drug carrier with anti-tumor effects, let alone the use of hydrophobic anticancer drugs as hydrophobic blocks Modification of hyperbranched polyamidoamine forms a polymer drug carrier with anti-tumor effect, and then the drug carrier forms micelles in water, and then carries the second anti-tumor drug, and also carries a therapeutic drug through electrostatic interaction. Gene, as a co-delivery vehicle for drugs and genes for the treatment of tumors

Method used

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  • Redox responsive amphiphilic copolymer as well as preparation method and application thereof
  • Redox responsive amphiphilic copolymer as well as preparation method and application thereof
  • Redox responsive amphiphilic copolymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Example 1: Preparation of Compound III (N,N'-bis(acryloyl)cystamine):

[0067]

[0068] Dissolve 2.5g of cystamine hydrochloride (compound II) and 1.8g of NaOH in 15.5ml of deionized water, and add a solution of acryloyl chloride in dichloromethane (3.3ml of acryloyl chloride in 3.3ml of anhydrous di Chloromethane), after the dropwise addition, remove the ice bath, react at room temperature for 6 hours, finish the reaction, add 200ml dichloromethane to the reaction solution for extraction, extract three times, combine the organic phases, and the organic phases are distilled under reduced pressure and vacuum-dried to obtain a white powdery substance , that is, compound III (N,N'-bis(acryloyl)cystamine).

[0069] Tested: 1 H NMR (600MHz, CDCl 3 ): δ6.68(s,1H), 6.34(dd, J=17.0,1.5Hz,1H), 6.24(dd,J=17.0,10.2Hz,1H), 5.69(dd,J=10.2,1.5Hz, 1H), 3.69 (q, J=6.4Hz, 2H), 2.90 (t, J=6.5Hz, 2H).

Embodiment 2

[0070] Embodiment 2: the preparation of compound IV (hyperbranched polyamidoamine PAAs):

[0071]

[0072] Dissolve 0.642g of compound III and 0.592g of anhydrous calcium chloride in 15ml of aqueous methanol (the volume ratio of methanol / water is 3 / 1). Under the protection of nitrogen, the temperature of the reaction solution is raised to 50°C, and 0.16ml of 1-(2-Aminoethyl)piperazine (AEPZ), after the dropwise addition is completed, keep the reaction at 50°C for 36 hours, then add 0.35ml 1-(2-Aminoethyl)piperazine (AEPZ) dropwise again, continue Insulate the reaction for 4 hours, end the reaction, add dilute hydrochloric acid to adjust the pH of the reaction system to 3-4, then add the reaction solution into a dialysis bag (MWcutoff=1000), dialyze for 24 hours, centrifuge to remove the precipitate, and freeze-dry the solution to obtain a light yellow viscous Thickness, that is, compound IV (hyperbranched polyamidoamine PAAs).

[0073] Tested: 1 H NMR (600MHz,D 2 O)δ3.60...

Embodiment 3

[0074] Embodiment 3: Preparation of redox-responsive amphiphilic hyperbranched polyamidoamine-gambogic acid copolymer PAG:

[0075]

[0076]Dissolve 0.5g gambogic acid (GA) and 0.1g 4-lutidine (DMAP) in 10ml of anhydrous dichloromethane, and add 0.3g 1-ethyl-(3-dimethyl Aminopropyl) carbodiimide (EDC), stirred in an ice bath for 1 hour, then added 1.5 g of compound IV, and reacted at room temperature for 24 hours. hours, centrifuged to remove the precipitate, and the solution was freeze-dried to obtain a yellow viscous substance, that is, a hyperbranched polyamidoamine-gambogic acid copolymer (PAG for short).

[0077] figure 1 is the NMR spectrum of PAG ( 1 H-NMR (DMSO-d)), among the figure, δ5.0-9.0ppm belongs to the characteristic peak (h) of gambogic acid, and simultaneously the characteristic peak (a-f) of CBA and 1-(2-aminoethyl) piperazine also Marked in the hydrogen spectrum, proves that the compound that makes is required hyperbranched polyamidoamine-gambogic aci...

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Abstract

The invention discloses a redox responsive amphiphilic copolymer as well as a preparation method and application of the redox responsive amphiphilic copolymer. The redox responsive amphiphilic copolymer is a compound with the structure of the formula I, wherein X is an antitumor active drug with carboxyl groups or carboxyl groups after derivatization of acetic anhydride. The redox responsive amphiphilic copolymer can be self-assembled to form micelles in water, hydrophobic ends of the inner layers of the micelles are encapsulated with hydrophobic antitumor drugs Y, and the micelles can further load treating genes Z by electrostatic interaction to obtain the micelles which simultaneously load therapeutic genes and chemotherapeutic drugs. The redox responsive amphiphilic copolymer and the micelles formed by self-assembling of the redox responsive amphiphilic copolymer and the micelles which simultaneously load the therapeutic genes and the chemotherapeutic drugs all can be used for preparing the antitumor drugs; furthermore, the redox responsive amphiphilic copolymer is simple in preparation method, does not need special equipment or harsh conditions, is easy to realize large-scale production and has very strong practical values.

Description

technical field [0001] The present invention relates to an amphiphilic copolymer and its preparation method and application, specifically, to a redox-responsive amphiphilic copolymer, its preparation method and its application in the field of anti-tumor, belonging to the pharmaceutical preparation technology field. Background technique [0002] As one of the major diseases threatening human health in the 21st century, cancer has the characteristics of low cure rate and high recurrence rate, and has become one of the most important diseases threatening human life and health. According to reports, in 2012, cancer caused a total of 8.2 million deaths worldwide, among which lung cancer, liver cancer, gastric cancer, and colorectal cancer were the main ones. In the past ten years, the supply of oncology drugs in the pharmaceutical industry has expanded by more than 60%. At present, more than 500 companies are engaged in the research and development of drugs in this field. In 201...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/107A61K47/59A61K48/00A61K31/7088A61K31/352A61K31/337A61P35/00C08G73/02
CPCA61K9/107A61K31/337A61K31/352A61K31/7088C08G73/028A61K2300/00
Inventor 张彤丁越兰金帅康亚楠路璐
Owner SHANGHAI UNIV OF T C M
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