A photoreducible self-degrading polymer and its preparation method and application
A technology of self-degradation and polymer materials, applied in the field of photoreduction self-degradation polymers and their preparation, can solve the problems of low drug release efficiency, dependence on exogenous stimuli, and inability to adjust, and achieve easy removal and metabolism, high biological Compatibility, the effect of overcoming steric barriers
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Embodiment 1
[0072]The photoreductive self-degradable material provided in Example 1 can be self-assembled to form nanovesicles after complexing with polyethylene glycol (Example 11, Application Example 4), and the self-assembled body can generate active DTT residues under exogenous light stimulation; Since the DTT residues are generated in situ near the disulfide group in the hydrophobic core of the self-assembly, it can effectively overcome the steric hindrance and osmotic barriers, greatly improve the efficiency of the stimulus response, and obtain a higher reductive degradation than the external reducing agent (10mM DTT) Efficiency and higher response drug release speed than traditional light-sensitive materials (without disulfide bond, comparative example 1). Furthermore, the concentration of in situ generated DTT residues (1 mM) required to achieve reductive self-degradation is much lower than the concentration of added DTT reducing agent (10 mM), thereby overcoming the concentration ...
Embodiment 2
[0079] In this example, photoreducible self-degradable polymer 2 was synthesized.
[0080] Get dithioerythritol (3.08g) dissolved in NaOH ethanol solution (40mL), ice bath cooling; dropwise add 2-(1-bromobutyl)-1,3-dinitrobenzene (13.9g) in ethanol The solution (40 mL) was naturally returned to room temperature and reacted for 8 hours, and the formed precipitate was suction-filtered, freeze-dried, and stored in the dark to obtain Intermediate 2.
[0081] Take intermediate 2 (2.29g) into the reaction flask, inject anhydrous dichloromethane (15mL), then add 2,2'-dithiodiacetic acid (0.73g) in dichloromethane solution (10mL), then add 1 -(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.2g) and 4-dimethylaminopyridine (0.02g), reacted at room temperature for 48 hours; after the reaction was completed, the product was reduced Concentrate under reduced pressure, precipitate three times with glacial ether, and dry in vacuum for 48 hours to obtain photoreducible self-degr...
Embodiment 3
[0083] In this example, photoreducible self-degradable polymer 3 was synthesized.
[0084] Take dithiothreitol (3.08g) and dissolve NaOH in ethanol solution (40mL), and cool in an ice bath; add dropwise N-dodecyl-2-iodo-2-(6-nitro-3,4- Methyldioxybenzene)-acetamide (18.1g) in ethanol solution (50mL), naturally returned to room temperature and reacted for 12 hours, the resulting precipitate was suction filtered, lyophilized, and stored in the dark to obtain intermediate 3.
[0085] Take intermediate 3 (2.62g) into the reaction flask, inject anhydrous tetrahydrofuran (15mL), then add 2,2'-dithiodiethanol (0.62g) in tetrahydrofuran (10mL), ethyl lysine diisocyanate ( 1.81 g) and 1 drop of stannous octoate, heated to 60° C. and reacted for 24 hours; after the reaction was completed, the product was concentrated under reduced pressure, precipitated with glacial ether three times, and dried in vacuum for 48 hours to obtain photoreducible self-degradable polymer 3.
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