Curcumin symmetrical derivative, preparation thereof and application thereof in preparation of antitumor drugs
A technology of curcumin and derivatives, applied in the new field of anticancer active drugs, can solve the problems of excipient toxicity, metabolism, degradation, unsatisfactory curcumin toxicity selectivity, unsatisfactory loading efficiency, etc. Achieve the effect of improving encapsulation drug loading, excellent selective toxicity, and excellent toxicity selectivity
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Embodiment 1
[0057] Embodiment 1: the synthesis of formula 2 (TK)
[0058] The synthetic reaction formula is:
[0059]
[0060] Anhydrous 3-mercaptopropionic acid (5.31 g, 50 mmol) and anhydrous acetone (5.81 g, 100 mmol) were added into a 25 mL three-necked flask, and then catalyzed with 2 drops of TFA. After stirring at 30 °C for 2 h, the flask was placed in a cooled ice bath to crystallize the product. Filter the crystals, rinse with n-hexane and cold water. Drying in a vacuum oven gave a white product.
Embodiment 2
[0061] Embodiment 2: (CUR 2 -TK, the synthesis of formula 1)
[0062] CUR 2 The synthetic reaction formula of -TK is shown in Reaction Formula 2:
[0063]
[0064]
[0065] Dissolve CUR (80.0mg, 0.22mmol) in 20Ml CH 2 Cl 2 , then linker TK (Formula 1, 25.2 mg, 0.1 mmol), EDC·HCl (76.8 mg, 0.40 mmol) and DMAP (2.5 mg, 0.02 mmol) were added. Stir at 30 °C for 1 h. After that, EDC·HCl (38.4mg, 0.20mmol) and DMAP (2.5mg, 0.02mmol) were added, and the reaction was stirred under the same condition for 24h. After the reaction, the organic solvent was rotary evaporated, then dissolved in 5mL DMSO and 15mL pure water, and dialyzed for 48h to remove small molecular impurities using a dialysis membrane (500D, MWCO). 2 Cl 2 and MeOH (V / V=95:5) as the eluent, purified by silica gel column chromatography, freeze-dried to obtain a dark red product, and the final product CUR 2 -TK was stored in a -20 °C freezer.
[0066] CUR 2 - UV-vis, fluorescence spectrum, FT-IR, HPLC spect...
Embodiment 3
[0070] Embodiment 3: (CUR 2 Preparation of -TK)-Polymer nanoparticles.
[0071] (CUR 2 -TK)-Polymer NPs preparation: 30mg CUR 2 -TK was dissolved in 0.3ml DMSO, (60, 30, 15, 10) mg PEG-PLGA was dissolved in 1ml dichloromethane (CUR 2 -TK: PEG-PLGA=1:2, 1:1, 2:1, 3:1), then mix the two and add dropwise in 5ml polyvinyl alcohol (PVA) solution (1%w / v), Use an ultrasonic liquid breaker (SONICS-VCX500, 35% AMP) to ultrasonically mix for 3 min, then add 40 ml of 0.1% PVA solution, stir magnetically at 600 rpm for 4 h, volatilize the organic solvent, centrifuge at 10000 rpm for 15 min at low temperature, wash 3 times, collect (CUR 2 -TK)-Polymer NP nanoparticles were freeze-dried for 24 hours, and the product NPs were stored in a -20°C refrigerator.
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