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Preparation method and application of j-aggregate photothermal nanoagent based on dyes and polymers

A technology of aggregates and block polymers, which is applied in the directions of photodynamic therapy, preparations for in vivo experiments, and medical preparations of inactive ingredients, etc. It can solve the problems of stability, uncertain biological toxicity, etc., and achieve the effect of constant photothermal conversion effect, outstanding photothermal stability, and good therapeutic effect.

Active Publication Date: 2022-07-05
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As far as the currently reported photothermal reagents are concerned, organic small molecule photothermal reagents require a complex synthesis process, making it difficult to obtain photothermal reagents with low toxicity, high thermal conversion efficiency, and near-infrared absorption, and the prepared Organic small molecule photothermal reagents often do not have photostability and are prone to photobleaching during the treatment process; while inorganic photothermal reagents have near-infrared absorption and high photothermal conversion efficiency, but their uncertain biological toxicity and The disadvantages such as refractory degradation also limit the application of this type of material.

Method used

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  • Preparation method and application of j-aggregate photothermal nanoagent based on dyes and polymers
  • Preparation method and application of j-aggregate photothermal nanoagent based on dyes and polymers
  • Preparation method and application of j-aggregate photothermal nanoagent based on dyes and polymers

Examples

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Embodiment 1

[0025] Example 1: Synthesis of Four Hydrophobic BODIPY Dye Molecules, See Attachment for Molecular Structure image 3 , the synthetic route is attached figure 1 . Synthesis of compound 2: Compound 1 (1.83 g, 5.0 mmol) and N-chlorosuccinimide (NCS) (2.0 g, 15.0 mmol) were dissolved in 100 mL of methanol, and a small amount of thiourea (0.1 g), react at 30°C for about 3h. During the period, the plate was monitored. When the compound 1 was consumed, the reaction was stopped. After the solvent was removed by rotary evaporation, the red solid product 2 (1.83g) was obtained after purification by column chromatography PE / DCM (1 / 1, v / v). The yield was 84.3%. 1 H NMR (400MHz, CDCl 3 )δ(ppm) 6.98(s, 2H), 2.58(s, 6H), 2.36(s, 3H), 2.08(s, 6H), 1.37(s, 6H).

[0026] compound Me Ph-BD Cl Synthesis. 3,4-Dimethoxybenzaldehyde (498.5 mg, 3.0 mmol) was dissolved in 50 mL of dry acetonitrile solution and a small amount of molecular sieve was added as a water scavenger, 0.5 mL of piperid...

Embodiment 2

[0033] Example 2. Dye Ph-BD Cl Method for preparing J-aggregate photothermal reagent J1: Ph-BD Cl Dissolve in dry acetone to give a saturated solution. Weigh high polymer PEG 113 -b-PCL 8 Add 200 μL of acetone to 10 mg, stir at 37°C to fully dissolve it, then add 10 mL of ultrapure water to it, stir at 37°C and 900RPM for 3 minutes, and then add Ph-BD dropwise to it quickly Cl Add 1 mL of acetone saturated solution of dye molecules, continue stirring for 24 hours under these conditions, and pass through a 0.45 μm water filter to obtain Ph-BD Cl Dye J-aggregate photothermal reagent J1 at a concentration of approximately 60 μM. Its absorption spectrum changes as follows Figure 4 shown.

Embodiment 3

[0034] Example 3. Ph-BD Br Preparation method of J-aggregate photothermal reagent J3 constructed by dyes and polymers: Ph-BD Br The molecule is dissolved in acetone to give its saturated solution. Weigh 10mg of polymer PEG 113 -b-PCL 8 , add a small amount of acetone, stir at 37 ° C to fully dissolve, then add 10 mL of ultrapure water to it, stir at 37 ° C and 900RPM for 3 min, and then quickly add 3 mL of saturated solution of BODIPY dye molecules to it, under this condition Continue stirring for 24 hours. Ph-BD can be obtained Br J-aggregate solution J2 before dye structure remodeling. Then, the solution was added to a millipore ultrafiltration tube with a filter membrane molecular weight cut-off of 10K and a volume of 15 mL, and centrifuged 6 times at 2000 RPM for 1 hour each time. After each centrifugation, the lower aqueous solution was discarded, and ultrapure water was added to the upper centrifuge tube to 15 mL, and centrifugation was continued. Finally, 0.6 mL...

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Abstract

The invention relates to a preparation method and application of a J aggregate photothermal nano-agent constructed based on dyes and polymers. The nanophotothermal reagent takes fluoroborondipyrrole dye molecules and high molecular polymers as basic building units, and is co-assembled in an aqueous solution to obtain a J-aggregate nanosolution that can be stably dispersed in the aqueous system. The formation of J aggregates changes the photophysical / chemical properties of the dye molecules, the absorption spectrum is red-shifted by more than 100 nanometers, and the molar extinction coefficient increases significantly, showing a good photothermal conversion effect. Combined with further supramolecular structure remodeling, the morphology of the J-aggregate material is transformed into nanoparticles, the cellular uptake rate of the material is enhanced, and the biological application of the material is better realized. The J-aggregate nanophotothermal material proposed in the present invention has many advantages such as good biocompatibility, high photothermal conversion efficiency, and resistance to photobleaching, and has broad application prospects in the fields of photothermal therapy and photoacoustic imaging.

Description

technical field [0001] The invention belongs to the field of nano-biological materials, and in particular relates to a preparation method and biological application of a J-aggregate photothermal nano-material constructed by co-assembly of fluoroborondipyrrole (BODIPY) dye molecules and high molecular polymers. Background technique [0002] Photothermal therapy (PTT), as an important tumor treatment method, has attracted extensive attention of scientists due to its advantages of less trauma, simple treatment, and quick recovery. In photothermal therapy, photothermal agents convert light energy into heat energy, thereby achieving thermal ablation of tumors. As far as the currently reported photothermal reagents are concerned, the organic small molecule photothermal reagents require a complex synthesis process, making it difficult to obtain photothermal reagents with low toxicity, high thermal conversion efficiency, and near-infrared absorption. Organic small-molecule photothe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K41/00A61K47/34A61K49/22A61K49/00A61P35/00
CPCA61K41/0057A61K47/34A61K49/22A61K49/0021A61K49/0054A61P35/00
Inventor 李昌华苏美慧
Owner NANKAI UNIV
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