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Organic boron photosensitizer based on aggregation-induced emission, and application thereof in treatment of multi-drug-resistant bacterium infection

A technology for aggregation-induced luminescence and multi-drug-resistant bacteria, which is applied in the field of biomedicine, can solve the problems of poor inhibition or killing of multi-drug-resistant bacteria, and achieve the effect of good generation of active oxygen clusters and easy synthesis

Active Publication Date: 2021-08-06
HKUST SHENZHEN RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The object of the present invention is to provide an organoboron photosensitizer with aggregation-induced luminescent properties and its preparation method and application, to solve the problem of multidrug-resistant bacteria in the prior art Clinical drug resistance, and poor inhibition or killing of multi-drug resistant bacteria

Method used

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  • Organic boron photosensitizer based on aggregation-induced emission, and application thereof in treatment of multi-drug-resistant bacterium infection
  • Organic boron photosensitizer based on aggregation-induced emission, and application thereof in treatment of multi-drug-resistant bacterium infection
  • Organic boron photosensitizer based on aggregation-induced emission, and application thereof in treatment of multi-drug-resistant bacterium infection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Embodiment 1: the preparation of product

[0085] (1) Synthesis of DMA-AB

[0086] In a 100mL single-necked round bottom bottle equipped with a condenser, add 4-dimethylaminobenzaldehyde (4-dimethylaminobenzaldehyde, DMA-P-CHO; 1.5g, 10mmol), benzohydrazide (BHA; 1.36g , 10mmol) and ethanol (EtOH; 20mL) solvent, heated to reflux for 24 hours. After the reaction mixture was cooled back to room temperature, it was filtered and washed three times with cold ethanol solvent to obtain a white DMA-AH intermediate solid product, which was directly carried out to the next reaction without further purification after vacuum drying. Add DMA-AH allyltrimethylsilane (ATMS; 2.05mL, 12.9mmol), boron trifluoride diethyl ether (BF 3 OEt 2 1.87mL, 14.87mmol) and dry dichloroethane (DCE; 50 mL) solvent, after heating to reflux for more than two hours, the reaction was monitored with a silica gel plate (TLC); after confirming that the reaction was complete, the solvent was drained, And ...

Embodiment 2

[0103] Example 2: Research on the optics, aggregation-induced luminescence, and generation of active oxygen characteristics of the product

[0104] Two organoboron fluorescent products (DMA-AB-F and F-AB-DMA) are taken as examples to illustrate their optical properties, aggregation-induced luminescence, and generation of active oxygen. The same is true for other products, and details will not be repeated here.

[0105] (1) Research on optical properties

[0106] The ultraviolet-visible (UV-vis) absorption spectrum and photoluminescence (PL) spectrum of DMA-AB-F and F-AB-DMA in tetrahydrofuran (THF) solution are respectively as follows figure 2 and 3 shown. The maximum absorption wavelengths of the two products in THF solution are both at 415nm, but the emission wavelengths are at 473 and 555nm respectively, and the Stokes shifts are 58 and 140nm respectively. The main reason is that F-AB-DMA has a larger ground state and This is caused by the difference in the dipole mome...

Embodiment 3

[0115] Embodiment 3: product is in the treatment of multi-drug resistant bacteria infection

[0116] (1) Bacterial culture, staining and imaging

[0117] Multidrug-resistant Escherichia coli (MDR E.coli) and methicillin-resistant Staphylococcus aureus (MRSA) were cultured in LB medium under the conditions of 37° C. and 220 rpm. Bacteria were harvested by centrifugation at 3500 rpm for 10 minutes and washed twice. will contain 1×10 9 Bacterial colony forming units (CFU mL -1) in phosphate-buffered saline (PBS) solution (10 μM, 100 μL) was transferred to a 1.5-mL microcentrifuge tube. After vortexing, the bacteria were incubated at 37 °C for 1 hour at a shaking speed of 220 rpm. To take fluorescent images, transfer 10 µL of the stained bacteria solution to a glass slide, which is then covered with a coverslip. Such as Figure 15 and Figure 16 As shown, the DMA-AB-F photosensitizer successfully infects multidrug-resistant bacteria using a confocal laser scanning microscop...

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Abstract

The invention relates to an organic boron photosensitizer based on aggregation-induced emission, a preparation method thereof and application of the organic boron photosensitizer in photodynamic therapy for multi-drug-resistant bacterium infection. A series of synthesized organic boron photosensitizers based on aggregation-induced emission are easy to synthesize, show good aggregation-state luminescence and active oxygen generation characteristics, are used as photosensitizers for labeling and photodynamic therapy of multi-drug-resistant bacterium infection, and have very important significance and value in the technical field of biological medicines.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to an organoboron photosensitizer based on aggregation-induced luminescent properties, a preparation method thereof, and an application thereof in the treatment of multidrug-resistant bacteria infection. Background technique [0002] Multidrug-resistant bacteria (MDR bacteria), also known as multidrug-resistant microorganisms, are the result of bacterial variation and overuse of antibacterial drugs, mainly referring to three or more types of antibacterial agents (different in structure or mechanism of action). Bacteria that are resistant to both drugs (one or more of each class). The problem of nosocomial infections caused by bacterial drug-resistant and multidrug-resistant bacteria is becoming more and more serious. In the past 30 years, due to bacterial mutation, overuse of antibacterial drugs and other problems, the increase and spread of drug-resistant strains have resulted...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06H01L51/54A61K41/00A61P31/04G01N21/64
CPCC07F5/022C09K11/06A61K41/0057A61P31/04G01N21/6428G01N21/6402C09K2211/1007C09K2211/1055G01N2021/6432H10K85/656Y02B20/00Y02A50/30
Inventor 唐本忠倪侦翔李凯闵天亮牛广乐
Owner HKUST SHENZHEN RES INST
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