Whole-cell tumor nano-vaccine as well as preparation method and application thereof
A nano-vaccine and whole-cell technology, applied in anti-tumor drugs, pharmaceutical formulations, medical preparations with inactive ingredients, etc., can solve the problems of delaying the patient's treatment time and the long process of obtaining neoantigens, and achieve personalized treatment, Highly effective anti-tumor recurrence and metastatic effects, and uptake-increasing effects
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preparation Embodiment 1
[0056] Preparation Example 1: Preparation of engineered cell membrane
[0057] CT-26 cells treated with oxaliplatin were collected, washed with Tris-HCl pH 7.0, sucrose, and D-mannitol, and then homogenized in the presence of a mixture of phosphatase inhibitors and protease inhibitors. Cells are mechanically disrupted and cell membranes are harvested by ultracentrifugation. The obtained cell membranes were washed with aqueous ethylenediaminetetraacetic acid and stored at -20°C. The total protein content of the membrane was quantified by BCA protein detection kit.
[0058] figure 1 It is a transmission electron microscope photo of the prepared engineered cell membrane extruded by a nano-extruder. The cell membrane has a good membrane structure after being negatively stained with uranyl acetate, and the thickness is about 10nm.
preparation Embodiment 2
[0059] Preparation Example 2: Synthesis of Polymer
[0060]
[0061] Dissolve 4-cyano-4-[[(dodecylthio)thionemethyl]thio]pentanoic acid (CTA) (19.3 mg, 0.048 mmol) in 5 mL of N,N-dimethylformamide , to which was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (27.5 mg, 0.144 mmol), 1-hydroxybenzotriazole (HOBT) (19.4 mg, 0.144mmol), triethylamine (TEA) (16.16mg, 0.160mmol) reacted at room temperature for 1.5h. Subsequently, mPEG was added to 113 -NH 2 (200.8mg, 0.040mmol), after reacting at room temperature for 24h, the reaction solution was dialyzed with ethanol and deionized water. The molecular weight cut-off of the dialysis bag was 3500D. After lyophilization, 182mg of a light yellow powdery solid was obtained, with a yield of 84.3%. 1 H NMR (400MHz, CDCl 3 )δ3.84–3.80(m,3H),3.69–3.62(m,456H),3.56(dd,J=9.9,5.1Hz,6H),3.47(dd,J=9.2,4.7Hz,6H),3.39 (s,3H),3.35–3.30(m,2H),2.51(d,J=3.9Hz,3H),1.69(dt,J=15.0,7.5Hz,2H),1.45–1.36(m,4H), 1.35–1.28(m,...
preparation Embodiment 3
[0063] Preparation Example 3: Preparation of acid-sensitive polymer-immune adjuvant conjugate
[0064]
[0065] Compound 1 (6.0g, 0.04mol), TEA (8.08g, 0.08mol) were dissolved in 10mL of dichloromethane, and 10mL of methacryloyl chloride (2.08g, 0.08mol) was slowly added dropwise thereto under an ice-water bath. Chloromethane solution, dropwise, react at room temperature for 12h. The reaction solution was washed with water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and separated by a column to obtain 3.8 g of compound 2 with a yield of 87.2%. 1 H NMR (400MHz, CDCl 3 )δ6.15(s,1H),5.64–5.55(m,1H),4.35–4.30(m,2H),3.79–3.75(m,2H),3.75–3.71(m,2H),3.69(s, 4H),3.64–3.60(m,2H),1.96(s,3H).
[0066] Compound 2 (0.20g, 0.91mmol), N,N-diisopropylethylamine (DIEA) (354mg, 2.75mmol) was dissolved in 10mL tetrahydrofuran, and di(p-nitrophenyl)carbonic acid was added thereto under an ice-water bath Ester (NPC) (418mg, 1.37mmol), react at room temperature for ...
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