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Polycation inclusion complex, and preparation method and purpose thereof

A technology of polycation and inclusion compound, which is applied in the directions of non-active components of polymer compounds, drug combinations, pharmaceutical formulations, etc., can solve the problem that it is difficult to meet the requirements of stable cell dissociation and release, lack of selectivity, application scope and use effect limitations. And other issues

Active Publication Date: 2016-01-27
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned carriers lack selectivity to different acidic environments inside and outside the cell. When used for the delivery of nucleic acid drugs, it is difficult to meet the requirements of stable extracellular existence, rapid intracellular dissociation and release of the entrapped nucleic acid drugs. effects are severely limited

Method used

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  • Polycation inclusion complex, and preparation method and purpose thereof
  • Polycation inclusion complex, and preparation method and purpose thereof
  • Polycation inclusion complex, and preparation method and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1: the synthesis of β-cyclodextrin initiator

[0058] Weigh 4.5 mmol of β-cyclodextrin, dissolve it in 30 ml of anhydrous N,N-dimethylacetamide under stirring, and add 22.5 mmol of triethylamine. Weigh 22.3mmol of 2-bromoisobutyryl bromide and dissolve it in 10ml of anhydrous N,N-dimethylacetamide. The 2-bromoisobutylacyl bromide solution was slowly added dropwise to the β-cyclodextrin solution, stirred in an ice bath, then slowly raised to room temperature, and continued to stir overnight. After the reaction was completed, precipitate with ether and use acetone to obtain 3.3 g of 4-substituted β-cyclodextrin initiator (yield: 42.4%). 1 HNMR (CDCl 3 ): δ=1.88(24H,-OCO-C(CH 3 ) 2 Br), 3.00-6.00 (66H, -OH and -CH-β-CD).

Embodiment 2

[0059] Embodiment 2: the synthesis of adamantane initiator

[0060] Weigh 3.0 g (18.0 mmol) of adamantane methanol and dissolve it in 50 ml of dichloromethane, and then add 3 ml (21.6 mmol) of triethylamine to the solution. Measure 2.7ml (21.8mmol) of 2-bromoisobutyryl bromide, dissolve it in dichloromethane, and add it dropwise to the adamantane methanol solution under ice-cooling. After the dropwise addition, the stirring was continued overnight. After the solution was concentrated by rotary evaporation, the product was purified with a silica gel chromatography column to obtain 4.6 g of adamantane initiator (yield: 81%). 1 HNMR (CDCl 3 ): δ=2.00 (3H, CH), 1.95 (6H, CH 2 ), 1.69 (6H, -C (CH 3 ) 2 Br), 1.58 (6H, CH 2 ).

Embodiment 3

[0061] Example 3: Synthesis of polydiisopropylaminoethyl methacrylate modified β-cyclodextrin

[0062] Take 0.3 g of the β-cyclodextrin initiator synthesized in Example 1 and dissolve in 1.5 ml N,N-dimethylacetamide and stir until dissolved, add 1 ml of diisopropylaminoethyl methacrylate (DPMA) and catalyst Pentamethyldiethylenetriamine (PMDETA) 132μl, add catalyst cuprous bromide 90mg under anaerobic conditions, stir and react at 40°C for 24 hours, peroxide column, obtain polydiisopropylaminoethyl methacrylate modified β-cyclodextrin 1.14 g (yield: 83%). 1 HNMR(DMF): δ=1.88-2.25(44H,-OCO-C(CH 3 ) 2 -CH 2 -CCH 3 Br), 2.74(8H, CH), 3.08(8H, CH 2 ), 3.99 (8H, CH 2 ), 3.00-6.00 (66H, -OH and -CH-β-CD). Its NMR data are as figure 1 shown in B.

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Abstract

The invention relates to a poly(2-diisopropylaminoethyl methacrylate) modified beta-cyclodextrin and aminated poly(glycidyl methacrylate) modified adamantane diblock host-guest polycation inclusion complex, a synthetic method thereof, a cationic micelle which is prepared from the above polycation inclusion complex and possesses dual acid sensitivities and a preparation method for the cationic micelle. Due to the fact that the cationic micelle possesses the dual acid sensitivities, the hydrophilic external layer of the micelle is capable of combining with proton and showing positive electricity under a neutral physiological condition that pH is 7.4, and the hydrophobic internal layer of the micelle is capable of combining with proton and being dissociated in a weakly acidic environment with pH lower than 6.3. The average hydrodynamics particle size of the cationic micelle is preferably 20-200 nm. The invention also relates to application of the cationic micelle with dual acid sensitivities to nucleic acid medicament conveying, and the cationic micelle is mainly applied to reverse the multidrug resistance of cancer cells or inhibiting cancer cell transfer.

Description

technical field [0001] The invention relates to a polycation clathrate, in particular to a diisopropylaminoethyl methacrylate modified β-cyclodextrin-aminated polyglycidyl methacrylate modified adamantane diblock host-guest A polycation clathrate, a synthesis method thereof, and a cationic micelle with double acid sensitivity prepared from the polycation clathrate and a preparation method thereof. The invention also relates to the application of the double acid-sensitive cationic micelles in the delivery of nucleic acid drugs, mainly for reversing the multidrug resistance of cancer cells or inhibiting the metastasis of cancer cells. Background technique [0002] Malignant tumor (cancer) has the characteristics of low cure rate, high recurrence rate and high mortality rate, and has become one of the major diseases threatening human health. In recent years, ribonucleotide (RNA) interference therapy based on cancer molecular biology has injected new vitality into cancer treatm...

Claims

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Application Information

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IPC IPC(8): C08J3/00C08F251/00C08F220/34C08B37/16C08F120/32C08F8/32A61K48/00A61K47/40A61P35/04
Inventor 李亚平于海军陈宪智
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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