An integrated nanosystem and preparation method for liver-targeted co-delivery of genes/drugs
A liver-targeting, copolymer technology, applied in the field of biomedicine, can solve the problem of underutilization, and achieve the effect of promoting real-time imaging, low cytotoxicity, and reducing drug leakage
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Embodiment 1
[0059] Embodiment 1: the preparation of bromorhodamine B initiator
[0060] Weigh 15.52g (25.00mmol) of ethylene glycol and 1.01g (10.00mmol) of triethylamine in a 100mL Erlenmeyer flask, stir in an ice-water bath to 0°C, and add 1.20mL (10.00mmol) of 2 -Bromoisobutyryl bromide, then slowly warmed up to room temperature, and magnetically stirred for 3h. The reacted solution was quenched by adding 100 mL of deionized water, and then extracted with dichloromethane (100 mL×3). The collected organic phases were extracted with deionized water (100 mL×3). An appropriate amount of anhydrous magnesium sulfate was added to the extracted organic phase, and dried for 12 hours. After filtration, the oily crude product was obtained by rotary evaporation, and the product was distilled under reduced pressure (85°C, 30mTorr) to obtain a colorless viscous product, hydroxyethyl isobromobutyrate.
[0061] Get 4.81g (10.00mmol) rhodamine B, 2.90g (15.00mmol) 1-ethyl-(3-dimethylaminopropyl) car...
Embodiment 2
[0062] Example 2: 3-Azido-2-hydroxypropyl methacrylate GMA-N 3 preparation of
[0063]Dissolve 3.71g (57.00mmol) sodium azide, 3.81g (45.20mmol) sodium bicarbonate in 60mL tetrahydrofuran / water (5:1v / v) and stir, slowly add 5.42g (37.80mmol) glycidyl methacrylate Ester, reaction at room temperature for 48h. After removing the insoluble salt by filtration, the solvent was removed by rotary evaporation, and the obtained concentrate was extracted twice with dichloromethane, and then the obtained organic phase was dried and filtered with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and the solvent was passed through a silica gel column (eluent : n-hexane / ethyl acetate volume ratio=9:1) separated to obtain 3-azido-2-hydroxyl propyl methacrylate. For specific methods, reference can be made to literature (Polymer Chemistry, 2015, 6, 3875-3884; Soft Matter, 2009, 5, 4788-4796).
Embodiment 3
[0064] Embodiment 3: Rhodamine B modified copolymer (RhB-PDMAEMA25-c-PGMA50-N 3 ) preparation
[0065] Accurately weigh 70.0mg (0.10mmol) bromorhodamine B initiator, 484.0mg (2.75mmol) monomer DMAEMA and 1.01g (5.50mmol) compound 3-azido-2-hydroxypropyl methacrylate and add to 25mL In a round bottom flask, dissolve with 2mL tetrahydrofuran, and pass argon gas for 30 minutes to remove oxygen in the flask. Wherein the monomer DMAEMA needs to remove the stabilizing agent therein in advance, is about to pass the DMAEMA crude product through the basic alumina column quickly. Under the protection of nitrogen, 18.9 mg (0.10 mmol) of CuBr and PMDETA (28 μL, 0.10 mmol) were successively added, the flask was sealed, and the reaction was carried out at room temperature for 8 h under the protection of nitrogen. After the reaction is over, add tetrahydrofuran (10 mL) to the reaction solution, fully stir and dissolve the reaction solution in the bottle, pass through a neutral alumina colu...
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