Beta-cyclodextrin-adriamycin prodrug molecule with pH responsiveness and preparation method thereof
A technology of cyclodextrin and doxorubicin, which is applied in the field of β-cyclodextrin-doxorubicin prodrug molecule and its preparation, can solve the problem of damage to normal human cells, achieve good water solubility and biocompatibility, The effect of fast speed and mild reaction conditions
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Embodiment 1
[0042] 1) Synthesis of 6-esterified β-cyclodextrin
[0043] Weigh 117.2 mg of mono-6-deoxy-6-propargylamine-β-cyclodextrin and 25.8 mg of ethyl azide bromoacetate respectively, add 1.5 mL of dry N, N-dimethylformamide as a solvent, and Fully dissolved under stirring conditions. Then 9.3 mg of tris(triphenylphosphine)copper bromide was added, and nitrogen gas was introduced for 15 minutes. The system was sealed and the reaction was stirred at 60 °C for 24 h. After the reaction was completed, the resulting mixed solution was precipitated in 150 mL of cold acetone, and the solid product was filtered out. After the solid product was vacuum-dried at room temperature for 1-2 days, it was dissolved in N,N-dimethylformamide, precipitated in 150 mL of cold acetone, and the solid product was filtered out, and the dissolution-precipitation process was repeated twice to obtain the product , that is, β-cyclodextrin esterified at the 6-position;
[0044] 2) Synthesis of β-cyclodextrin w...
Embodiment 2
[0049] 1) Synthesis of 6-esterified β-cyclodextrin
[0050] Weigh 117.2 mg of mono-6-deoxy-6-propargylamine-β-cyclodextrin and 38.7 mg of ethyl azide bromoacetate respectively, add 1.5 mL of dry N, N-dimethylformamide as a solvent, and Fully dissolved under stirring conditions. Then 9.3 mg of tris(triphenylphosphine)copper bromide was added, and nitrogen gas was introduced for 15 minutes. The system was sealed and the reaction was stirred at 70 °C for 18 h. After the reaction was completed, the resulting mixed solution was precipitated in 150 mL of cold acetone, and the solid product was filtered out. After the solid product was vacuum-dried at room temperature for 1-2 days, it was dissolved in N,N-dimethylformamide, precipitated in 150 mL of cold acetone, and the solid product was filtered out, and the dissolution-precipitation process was repeated twice to obtain the product , that is, the 6-esterified β-cyclodextrin.
[0051] 2) Synthesis of β-cyclodextrin with 6-position...
Embodiment 3
[0056] 1) Synthesis of 6-esterified β-cyclodextrin
[0057] Weigh 117.2 mg of mono-6-deoxy-6-propargylamine-β-cyclodextrin and 51.6 mg of ethyl azide bromoacetate respectively, add 2 mL of dry N, N-dimethylformamide as a solvent, and stir under magnetic force fully dissolved under the conditions. Then 9.3 mg of tris(triphenylphosphine)copper bromide was added, and nitrogen gas was introduced for 15 minutes. The system was sealed and the reaction was stirred at 65 °C for 20 h. After the reaction was completed, the resulting mixed solution was precipitated in 150 mL of cold acetone, and the solid product was filtered out. After the solid product was vacuum-dried at room temperature for 1-2 days, it was dissolved in N,N-dimethylformamide, precipitated in 150 mL of cold acetone, and the solid product was filtered out, and the dissolution-precipitation process was repeated twice to obtain the product , that is, the 6-esterified β-cyclodextrin.
[0058] 2) Synthesis of β-cyclode...
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