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Preparation method of fluorinated poly(amide amine) and its application as vaccine immune adjuvant

An immune adjuvant, amidoamine technology, applied in the field of biomedical materials, can solve problems such as hyperbranched polymerization modification

Active Publication Date: 2020-12-11
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, there has been no report on the modification of hyperbranched poly(amide amines) containing disulfide bonds as a vaccine delivery system.

Method used

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  • Preparation method of fluorinated poly(amide amine) and its application as vaccine immune adjuvant
  • Preparation method of fluorinated poly(amide amine) and its application as vaccine immune adjuvant
  • Preparation method of fluorinated poly(amide amine) and its application as vaccine immune adjuvant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] The synthetic route of fluorinated poly(amide amine) is as figure 1 shown. Made by the following steps:

[0061] (1) Synthesis of N,N'-cystamine bisacrylamide (CBA)

[0062] Use acryloyl chloride and cystamine dihydrochloride to synthesize the intermediate product N,N'-cystamine bisacrylamide (CBA). The specific steps are: dissolve 3.304mL acryloyl chloride (0.04mol) in 3.33mL dichloromethane (DCM) and NaOH solution (0.4 g / mL, 0.04 mol) was added dropwise to cystamine dihydrochloride solution (0.225 g / mL, 0.016 mol) alternately in an ice bath, and then the mixture was stirred at room temperature for 8 Hour. Then use 10 times the volume of DCM in the reaction mixture to extract the product in a separatory funnel, collect the lower layer extract, and wash with saturated NaHCO 3 solution, saturated NaCl solution and ultrapure water to wash the extract. The CBA was then collected during the process, the DCM was removed by a low pressure rotary evaporator and stored for...

Embodiment 2

[0070] The synthetic route of fluorinated poly(amide amine) is as figure 1 shown. Made by the following steps:

[0071] (1) Synthesis of N,N'-cystamine bisacrylamide (CBA)

[0072] The method is the same as step (1) in Example 1.

[0073] (2) Synthesis of poly(amide amine) (HPAA)

[0074] Method is the same as step (2) in embodiment 1.

[0075] (3) Synthesis of fluorinated poly(amide amine) (HPAA-F7)

[0076] HPAA-F7 is synthesized by anhydride reaction, the specific steps are: 0.05g HPAA and 0.05g heptafluorobutyric anhydride (1.8mmol) are dissolved in 10mL methanol to obtain a methanol solution; then 0.03mL triethylamine (0.21mmol) Added directly to the methanol solution. The reaction mixture was stirred for 48 h and then dialyzed for 48 h against a dialysis membrane with a molecular weight cut off of 1000 using ultrapure water as the dialysate. The product was lyophilized to yield fluorinated poly(amidoamine) (HPAA-F7).

[0077] HPAA-F7 in D 2 in O 1 The F NMR col...

Embodiment 3

[0079] The synthetic route of fluorinated poly(amide amine) is as figure 1 shown. Made by the following steps:

[0080] (1) Synthesis of N,N'-cystamine bisacrylamide (CBA)

[0081] The method is the same as step (1) in Example 1.

[0082] (2) Synthesis of poly(amide amine) (HPAA)

[0083] Aqueous calcium chloride solution (0.04 g / mL, 13.2 mL) was mixed with CBA (0.64 g) dissolved in calcium chloride-methanol solution (0.04 g / mL, 40 mL). Then while the above solution was heated to 50°C, AEPZ (aminoethylpiperazine) (0.32 mL, 2.45 mmol) was added dropwise to the solution. After 24h, AEPZ (0.345 mL, 2.64mmol) was added and reacted for 8h. After the reaction, the pH of the reaction mixture was adjusted to 4-6 with HCl solution (4 mmol / ml). Then ultrapure water was used as dialysate, dialyzed in a dialysis membrane with a molecular weight cut-off of 1000 for 48 hours, and then freeze-dried to obtain HPAA.

[0084] (3) Synthesis of fluorinated poly(amide amine) (HPAA-F7)

[0...

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Abstract

The invention discloses a preparation method of fluorinated polyamide amine and application thereof serving as a vaccine immune adjuvant. The preparation method includes following steps: dissolving polyamide amine and heptafluobutryric anhydride into an organic solvent to obtain a mixed solution I; adding triethylamine into the mixed solution I, stirring for reaction, and performing dialysis and freeze-drying after reaction is finished to obtain fluorinated polyamide amine. Heptafluobutryric anhydride is used to modify polyamide amine, so that prepared fluorinated polyamide amine has positivecharge in neutral pH environment, antigen ovalbumin can be wrapped through electrostatic attraction to form a nano preparation with the positive charge, and the preparation can effectively promote intracellular release of antigen protein and cytoplasm delivery. Therefore, fluorinated polyamide amine prepared by the method can serve as a vaccine delivery system to induce cellular immunological response so as to realize effective antitumor immunotherapy.

Description

technical field [0001] The invention belongs to the field of biomedical materials, in particular to a preparation method of fluorinated poly(amide amine) and its application as a vaccine immune adjuvant. Background technique [0002] Tumor vaccines induce specific anti-tumor immunity by injecting specific tumor antigens into patients, and are widely used in tumor immunotherapy. A large number of studies have shown that inducing specific killing of tumor cells while avoiding damage to normal tissues is the key to overcoming the difficult problem of tumor treatment. Tumor vaccines can trigger tumor-specific immune responses and completely kill tumors without damaging normal tissues, so this is an ideal tumor therapy. However, tumor antigens alone cannot induce strong antitumor immunity, so tumor antigens are often used together with immune adjuvants or vaccine delivery systems to elicit effective tumor-specific immune responses. In addition, the cellular immunity (non-humora...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F122/38C08F8/20A61K39/00A61K39/39A61P35/00
CPCA61K39/0011A61K39/39A61K2039/55511A61P35/00C08F8/20C08F122/385
Inventor 刘宗华薛巍袁洪媛
Owner JINAN UNIVERSITY
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