Preparation and application of a photosensitizer composite nano-functional material
A multifunctional, photosensitizer technology, applied in the fields of biomedicine and photodynamic therapy, can solve the problems of poor water solubility of cercosporin, undeveloped photodynamic therapy function, lack of targeting, etc., to reduce the leakage of photosensitizer, Facilitating real-time imaging and increasing the effect of release
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Embodiment 1
[0039] Embodiment 1: the preparation of bromorhodamine B initiator
[0040] Weigh 15.52g (25.00mmol) of ethylene glycol and 1.01g (10.00mmol) of triethylamine in a 100mL conical flask, stir, ice-water bath to 0 ℃, add dropwise under nitrogen atmosphere dissolved 1.20mL (10.00mmol) of 2 -bromoisobutyryl bromide, then slowly warmed to room temperature and magnetically stirred for 3 hours. The reacted solution was quenched by adding 100 mL of deionized water, and then extracted with dichloromethane (100 mL×3). The collected organic phases were extracted with deionized water (100 mL×3). An appropriate amount of anhydrous magnesium sulfate was added to the organic phase obtained by extraction and dried for 12 hours. After filtration, rotary evaporation was performed to obtain an oily crude product, which was distilled under reduced pressure (85° C., 30 mTorr) to obtain a colorless viscous product, hydroxyethyl isobromobutyrate.
[0041] Take 4.81g (10.00mmol) rhodamine B, 2.90g ...
Embodiment 2
[0042] Example 2: 3-azido-2-hydroxypropyl methacrylate GMA-N 3 preparation
[0043] Dissolve 3.71 g (57.00 mmol) sodium azide, 3.81 g (45.20 mmol) sodium bicarbonate in 60 mL tetrahydrofuran / water (5:1 v v -1 ), slowly added 5.42 g (37.80 mmol) of glycidyl methacrylate, and reacted at room temperature for 48 hours. After the insoluble salts were removed by filtration, the solvent was removed by rotary evaporation, the obtained concentrate was extracted twice with dichloromethane, the organic phase obtained was dried and filtered with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation. Ethyl acetate=9:1) was isolated to obtain 3-azido-2-hydroxypropyl methacrylate. For specific methods, please refer to the literature (Polymer Chemistry, 2015, 6, 3875-3884; Soft Matter, 2009, 5, 4788-4796).
Embodiment 3
[0044] Example 3: Rhodamine B covalently linked poly(N,N-dimethylaminoethyl methacrylate) and poly(3-azido-2-hydroxypropyl methacrylate) copolymer (RhB-PDMAEMA42- c-PGMA62-N 3 ) preparation
[0045] Accurately weigh 70.0mg (0.10mmol) of bromorhodamine B initiator, 484.0mg (2.75mmol) of monomer DMAEMA and 1.01g (5.50mmol) of compound 3-azido-2-hydroxypropyl methacrylate and added to 25mL In a round-bottomed flask, dissolve with 2 mL of tetrahydrofuran, and pass argon for 30 minutes to remove oxygen in the flask. The monomer DMAEMA needs to remove the stabilizer in advance, that is, the crude DMAEMA is quickly passed through the basic alumina column. Under nitrogen protection, 18.9 mg (0.10 mmol) of CuBr and PMDETA (28 μL, 0.10 mmol) were added successively, the flask was sealed, and the reaction was carried out at room temperature for 8 hours under nitrogen protection. After the reaction was completed, tetrahydrofuran (10 mL) was added to the reaction solution, and the react...
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