Quinoxaline-based D-A-pi-A type organic photosensitizer as well as synthesis method and application thereof

A photosensitizer, quinoxaline technology, applied in near-infrared organic photosensitizers and photosensitizer-based tumor photodynamic therapy applications, to achieve improved performance, easy access to raw materials, and good photodynamic therapy effects

Active Publication Date: 2020-12-18
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

No quinoxaline-based D-A-π-A organic photosensitizers have been reported for photodynamic therapy of tumors

Method used

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  • Quinoxaline-based D-A-pi-A type organic photosensitizer as well as synthesis method and application thereof
  • Quinoxaline-based D-A-pi-A type organic photosensitizer as well as synthesis method and application thereof
  • Quinoxaline-based D-A-pi-A type organic photosensitizer as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis of D-A-π-A Type Organic Photosensitizer HZ1 Based on Quinoxaline

[0041] (1) Synthesis of compound 2

[0042]

[0043] Under the protection of argon, in a 50mL two-necked round bottom flask, 862mg (2.0mmol) compound 1, 968mg (2.2mmol) dibromodiphenyl substituted quinoxaline, 3mL 2M K 2 CO 3 Aqueous solution was added to 20mL THF solvent, and then 115mg Pd(PPh 3 ) 4 catalyst. The reaction mixture was heated to 70 °C for 12 h. After cooling to room temperature, 30 mL of deionized water was added to the reaction liquid, and extracted several times with dichloromethane. The organic phase obtained by extraction and merging was dried with anhydrous magnesium sulfate and then rotary evaporated to remove the organic solvent, and the crude product was separated and purified by silica gel column chromatography, using normal hexane: dichloromethane (2:1) as mobile phase to obtain (0.97g ) orange solid compound 2, the yield was 73%. NMR: 1 H NMR (400MHz, CDCl ...

Embodiment 2

[0051] Photosensitizer HZ1 of embodiment 1 has been carried out AIE performance test, as figure 2 shown. The D-A-π-A type organic photosensitizer HZ1 based on quinoxaline was tested for its AIE performance in DMSO / toluene. It can be seen from Figure 2a and 2b that with the increase of the volume of toluene, the fluorescence intensity of the solution gradually increases, and when the volume of toluene accounts for 99%, the fluorescence intensity increases by 87 times. This shows that the photosensitizer has good AIE performance.

Embodiment 3

[0053] The photosensitizer HZ1 of Example 1 was tested by liquid ultraviolet and solid fluorescence. Such as image 3 shown. The UV-Vis absorption spectrum of dye HZ1 in DMSO is shown as image 3 As shown in a, the maximum absorption wavelength of the dye is 509nm, and the absorption spectrum covers most of the visible region. image 3 B is the solid-state fluorescence emission spectrogram of the dye, the fluorescence emission peak of the dye is at 679nm, and most of the areas on the right side of the dye are in the near-infrared wavelength region, which shows that the photosensitizer has very high near-infrared fluorescence emission performance.

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Abstract

The invention discloses a quinoxaline-based D-A-pi-A type organic photosensitizer as well as a synthesis method and application thereof, and belongs to the field of tumor photodynamic therapy. According to the invention, a series of novel D-A-pi-A structure near-infrared organic photosensitizers are synthesized by taking triphenylamine as an electron donor, diphenyl substituted quinoxaline as an additional receptor and pyridinium as a terminal electron acceptor. The introduction of diphenyl-substituted quinoxaline can effectively red-shift the light absorption and emission spectrum of the photosensitizer, and on the other hand, the existence of benzene rings on triphenylamine and quinoxaline with propeller structures can effectively inhibit the pi-pi accumulation effect between molecules,thereby improving the photodynamic therapy effect of the photosensitizer. By integrating the effects of the two aspects, the organic photosensitizer has a good application prospect in tumor photodynamic therapy.

Description

technical field [0001] The present invention relates to near-infrared organic photosensitizers and the application field of photosensitizer-based tumor photodynamic therapy, in particular to a quinoxaline-based D-A-π-A type near-infrared organic photosensitizer and its application in tumor photodynamic therapy. application. Background technique [0002] Cancer is a kind of disease that seriously threatens human health, and it is a health problem that is of great concern to all countries in the world. The current treatment methods for cancer mainly include surgery, chemotherapy, and radiation therapy. However, these treatment methods have certain defects, such as: surgical treatment is limited to direct resection of solid tumors visible to the naked eye to achieve the purpose of treatment, and cannot guarantee that all tumor cells will be removed, and there is a high risk of tumor recurrence; radiotherapy is due to the Radiation therapy is not specific, and it will inevitab...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/14A61K41/00A61P35/00G01N21/64
CPCC07D409/14A61K41/0057A61P35/00G01N21/6428G01N21/6486G01N2021/6439
Inventor 全云云黄祖胜王振操沈红艳沈超杰
Owner WENZHOU MEDICAL UNIV
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