Amphiphilic nanocage with active oxygen sensitivity, preparation method and application thereof
An oxygen-sensitive, amphiphilic technology, applied in the field of nanomedicine, can solve the problems of being easily affected by enzymolysis and other environmental factors, poor protein stability, etc., and achieve the effect of stable delivery and improved stability
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Embodiment 1
[0035] The synthesis of embodiment 1 betaine monomer (CBAA)
[0036] The reaction scheme is as follows:
[0037]
[0038] 7.80 g of 3-(dimethylaminopropyl)acrylamide (50 mmol), 11.48 g of methyl bromoacetate (75 mmol) and 30 ml of dichloromethane were added to a 100 ml round bottom flask with a magnetic stir bar. Under nitrogen protection, stir at room temperature for 6 hours. The precipitate was collected and washed with 500 ml of anhydrous acetone. The residual solvent was removed by vacuum drying to obtain 10.85 g of pure product, yield, 94.8%.
[0039] 1H NMR (400MHz, D2O) δ6.16(m, 2H), 5.72(t, 1H), 4.25(s, 2H), 3.75(s, 3H), 3.56(s=t, 2H), 3.31(t, 2H),3.21(s,6H),1.99(m,2H).
Embodiment 2
[0040] Example 2 Synthesis of thioketal-containing crosslinking molecules (TK)
[0041] The reaction scheme is as follows:
[0042]
[0043] First, add 5.68g (50mmol) of mercaptoethylamine and 7.80g (135mmol) of anhydrous acetone into a 100ml eggplant-shaped bottle, pass in saturated hydrogen chloride gas, stir and react at room temperature for 8h, and precipitate a white solid product. Wash twice. The crude product was then dried and recrystallized three times to obtain 4.21 g of the product, with a yield of 86%.
[0044] 1 H NMR (400MHz, CDCl3) δ2.83(s, 4H), 2.67(t, J=6.4Hz, 4H), 1.55(s, 6H), 1.33(s, 4H).
[0045]Add 1.94g of reactant a (10mmol) to a 100ml eggplant-shaped flask with a magnetic stirrer, add 20ml of dichloromethane, slowly add a mixture of 1.98g (22mmol) of acryloyl chloride and 15ml of dichloromethane dropwise at 0°C, and react After 30min, after returning to room temperature, stir for 4h. After the reaction was detected by TLC, 20ml of saturated sodi...
Embodiment 3
[0047] Example 3 Preparation of CBAA-TK nanocage (amphiphilic nanocage)
[0048] With the CBAA prepared in Example 1 and the TK prepared in Example 2 as raw materials, it is prepared through the following steps:
[0049] (1) Add 480mg sodium bis(2-ethylhexyl)sulfosuccinate (AOT) and 920mg polyethylene glycol lauryl ether (brij30) to a 30mL serum bottle with a magnetic stirrer, and add 15ml of n-hexane, stirred vigorously until completely dissolved, and passed nitrogen gas for 15min.
[0050] (2) Add 100mg CBAA monomer and 10mg TK monomer to the above solution;
[0051] (3) Nitrogen gas was introduced into the water phase for 3 minutes, and then the water phase was slowly added dropwise to the organic continuous phase; after ultrasonic treatment, a stable microemulsion was formed; Ammonium sulfate solution; after 5min, add 6uL tetramethylethylenediamine (TEMED) to initiate the polymerization reaction, and rapidly magnetically stir at 4°C; after reacting for 2h, precipitate th...
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