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Covalent organic framework material and preparation method and application thereof

A covalent organic framework and group technology, applied in the field of materials, can solve problems such as retention and lack of tumor targeting, and achieve high safety, improved therapeutic effect, and high biological safety.

Active Publication Date: 2022-02-08
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are only two kinds of drugs in clinical use, BPA and BSH, because BPA drugs cannot stay in tumor cells; BSH drugs lack tumor targeting, so boron drugs still need to be developed
No carborane-based covalent organic framework materials currently developed for BNCT therapy

Method used

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  • Covalent organic framework material and preparation method and application thereof
  • Covalent organic framework material and preparation method and application thereof
  • Covalent organic framework material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0172] Example 1: Synthesis of Carborane Covalent Organic Framework Materials

[0173] Synthesis of Monomeric B-CHO as Carborane Covalent Organic Framework Materials

[0174]

[0175] (1). Synthesis of compound 1

[0176] 4-iodobenzaldehyde (5.00g, 21.55mmol), p-toluenesulfonic acid (0.82g, 4.30mmol), ethylene glycol (14.45g, 215.50mmol) and molecular sieve (sodium-type A molecular sieve, spherical 3mm ~ 5mm) dissolved in CHCl 3 (50 mL), the mixture was heated to 80°C and stirred overnight. The reaction mixture was cooled to room temperature, water and NaHCO 3 (1M) was washed, and the aqueous layer was extracted with chloroform. Combined organic layers in NaSO 4 Dry over, filter and evaporate in vacuo to remove volatile compounds. The crude product was purified by silica gel column chromatography using a mixture of n-hexane and dichloromethane (1:2, v:v) as eluent to obtain compound 1 as a white solid (0.75 g, 50%). 1 H NMR (400MHz, chloroform-d) δ7.72(d, J=8.3Hz, 2H...

Embodiment 2

[0189] Example 2: Characterization of Covalent Organic Frameworks

[0190] 1. Characterization of XRD

[0191] To explore the crystallinity of the polymerized product, organic solvents of TAPB and B-CHO at a molar ratio of 2:3 were added to different solvents (2.5 mL) containing HAc (0.15 mL, 12 M), and the crystalline product was precipitated. Experimental test results such as image 3 As shown in Table 1, the reaction solvent plays a key role in the formation of the crystalline B-COF structure. The crystallinity of the polymerization product obtained in o-dichlorobenzene solvent is higher than that using other conventional reaction solvents. Moreover, the crystallinity of B-COF gradually increased when the reaction temperature was increased by 50 °C from room temperature. Under the action of polystyrene microsphere template additive, the B-COF obtained better crystallinity after etching away the template with toluene.

[0192] Table 1: Optimal conditions for B-COF (R.T m...

Embodiment 3

[0216] Example 3: Defects caused by boron neutron capture reaction

[0217] 1. Irradiation in test tube experiments found that drug release was accelerated

[0218] Experimental process such as Figure 16 depicted in .

[0219] In brief, considering the high correlation between pharmacokinetics and immunological responses, the release profile of DSPE-IMD@B-COF before and after thermal neutron irradiation was preliminarily explored. Here, using the IHNI-1 neutron flux 1.9×10 9 (cm -2 the s -1 ) thermal neutron irradiation for 30 min to treat DSPE-IMD@B-COF to monitor its release efficiency. Place the test tube at the neutron beam outlet of the BNCT to receive neutron irradiation, and compare the changes in the release of small molecule drugs before and after irradiation ( Figure 16 ). A control group was set up, and the non-neutron irradiation group was a control experiment.

[0220] The effect of neutrons on drug release was evaluated by calculating the cumulative rel...

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Abstract

The invention provides a covalent organic framework material as well as a preparation method and an application thereof. The covalent organic framework material comprises a structural unit with a regular hexagonal topological structure, and the structural unit comprises a compound as shown in a formula I and a compound comprising a core group and an arm group which are connected through an imine bond. By adopting the multifunctional boron capsule with high biocompatibility, BNCT and immunotherapy can be combined, the systemic anti-tumor treatment effect is achieved by enhancing the BNCT of local tumors, and wide prospects are shown in the aspect of treating far-end metastatic tumors through the local BNCT.

Description

technical field [0001] The invention belongs to the field of materials, in particular to carborane covalent organic framework materials. Background technique [0002] Covalent Organic Frameworks (COF) are a class of crystalline porous materials composed of organic molecular building blocks connected by covalent bonds. Due to its novel structure and excellent performance, COF has immediately aroused strong interest in the scientific community since it came out in 2005, and has made many important research progress in the fields of adsorption, catalysis, and optoelectronics. COF is an organic porous material with a high specific surface area, which has great advantages in nano-drug loading. However, its size is difficult to control and poor hydrophilicity restricts the application of COF materials in drug loading and in vivo delivery. [0003] Thermal and boron neutron capture therapy (BNCT) is a non-invasive treatment modality used to treat locally aggressive malignancies su...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00A61K41/00A61K45/00A61K47/54A61P35/00
CPCC08G83/008A61K47/545A61K45/00A61K41/00A61P35/00
Inventor 刘志博史亚鑫
Owner PEKING UNIV
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