Hyaluronic acid vitamin e succinate polymer and its preparation and use
A technology of hyaluronic acid and succinate, which is applied in the field of polymers, can solve the problem that normal cells and tissues are not killed, and achieve the effect of improving tumor targeting, high encapsulation rate, and simple and easy preparation method
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Embodiment 1
[0052] Example 1 The synthesis of ethylenediamine-vitamin E succinate (NH 2 -ED-VES)
[0053] Vitamin E succinate (VES, 0.53 g, 1 mol) was dissolved in 20 ml of dichloromethane (DCM) and placed in a 100 ml eggplant-shaped bottle. After being dissolved, add in 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 0.38g, 2mol) and 1-hydroxybenzotriazole (HoBt, 0.14 g, 1mol), and magnetically stirred for 1h under ice bath. Ethylenediamine (ED, 68 μl, 5 mol) was added, and reacted at 30° C. for 24 h under nitrogen protection.
[0054] Determination by NMR 1 HNMR hydrogen spectrum determines the structure (as shown below) of the compound in embodiment 1, selects solvent to be CDCl 3 , the result is as figure 1 . The chemical shift is 6.5ppm for the H in -NH-CO- in the amide bond, 2.5ppm and 3.5ppm for the ethyl-CH in ethylenediamine respectively 2 -CH 2 H in -, below 3.0ppm is a typical H peak in vitamin E succinate.
[0055]
Embodiment 2
[0056] Example 2 Synthesis of hyaluronic acid-ethylenediamine-vitamin E succinate (HA-ED-VES) (the degree of substitution of vitamin E succinate is 5%)
[0057] HA (140mg, -COOH, 0.36mM, M=7000) was dissolved in 5ml of anhydrous formamide, heated in a water bath at 50°C with magnetic stirring to dissolve, and cooled to room temperature. EDC (150 mg) and NHS (100 mg) were added, and magnetically stirred for 2 h in an ice bath. Then NH 2 - ED-VES (400 mg, 1.40 mM) was dissolved in dimethylformamide and slowly added dropwise to the HA mixture. The reaction was stirred at 60° C. for 24 h under a nitrogen atmosphere. The reaction mixture was dialyzed against distilled water for 2 days, filtered, and freeze-dried to obtain a white powder.
[0058] Determination by NMR 1 HNMR to determine the combination of compounds in Example 2, using DMSO-d 6 as the solvent, the result is as figure 2 Shown, chemical shift 0.8-1.0ppm is -CH in vitamin E succinate 3 peak, and the chemical sh...
Embodiment 3
[0059] Example 3 Synthesis of hyaluronic acid-ethylenediamine-vitamin E succinate (HA-ED-VES) (the degree of substitution of vitamin E succinate is 10%)
[0060] HA (140mg, -COOH, 0.36mM, M=7000) was dissolved in 5ml of anhydrous formamide, heated in a water bath at 50°C with magnetic stirring to dissolve, and cooled to room temperature. EDC (150 mg) and NHS (100 mg) were added, and magnetically stirred for 2 h in an ice bath. Then NH 2 - ED-VES (1.0 g, 3.50 mM) was dissolved in dimethylformamide and slowly added dropwise to the HA mixture. The reaction was stirred at 60° C. for 24 h under a nitrogen atmosphere. The reaction mixture was dialyzed against excess distilled water for 2 days, filtered, and freeze-dried to obtain a white powder.
[0061] Determination by NMR 1 HNMR to determine the combination of compounds in Example 3, using DMSO-d 6 As a solvent, chemical shift 0.8-1.0ppm is -CH in vitamin E succinate 3 peak, and the chemical shift 1.8-2.0ppm is NHCOCH in hy...
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