Aggregation-induced luminescence photosensitizer, preparation method and application

A technology of aggregation-induced luminescence and photosensitizer, which can be applied in the field of new drug development and can solve the problems of high price, poor effect, and high toxicity to human body.

Active Publication Date: 2022-07-15
无锡市觉新生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to design and synthesize a long-wavelength near-infrared aggregation-induced luminescence photosensitizer based on the characteristics of aggregation-induced luminescence molecules for the defects of traditional photosensitizers that are poor in effect, highly toxic to the human body, expensive and difficult to synthesize.

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  • Aggregation-induced luminescence photosensitizer, preparation method and application
  • Aggregation-induced luminescence photosensitizer, preparation method and application
  • Aggregation-induced luminescence photosensitizer, preparation method and application

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Embodiment 1

[0034] This embodiment relates to a quinoxalinone derivative, the preparation method of which is as follows: o-phenylenediamine (0.1mol, 10.8g) is dispersed in absolute ethanol (150mL), and ethyl pyruvate (0.12 g) is added dropwise under an ice bath mol, 13.92g), stirred at room temperature for 12h, the reaction solution was filtered, the filter cake was washed with absolute ethanol, and dried to obtain white powder 1a, (13.6g, yield 86%); 1a (20mmol, 3.2g), K 2 CO 3 (24mmol, 3.31g) was dispersed in acetone, then propenyl bromide (24mmol, 3.67g) was added dropwise with stirring, the reaction mixture was reacted at 62°C overnight, the solvent was evaporated to dryness, water and ethyl acetate were added to the residue, and the mixture was separated. The ethyl acetate phase was separated by silica gel column (petroleum ether:ethyl acetate=10:1), and purified to obtain 3.0 g of 1b with a yield of 54%. 1b (2mmol, 500mg) was suspended in acetic acid, 5-bromothiophene-2-carbaldehyd...

Embodiment 2

[0036] Prepare 1 mg / mL QCN stock solution in DMSO, and then pass different ratios of DMSO / H 2 The mixed solvent of O dilutes QCN into a solution with a concentration of 10 μg / mL, and its absorption spectrum is measured by a Thermo Electron-EV300 UV-Vis spectrophotometer. The maximum absorption wavelength of QCN is located at 560 nm. Then, the fluorescence spectrum of QCN was measured by steady-state time-resolved fluorescence spectrophotometer, and it was found that the maximum emission wavelength of QCN reached 800 nm. Then, the reactive oxygen species generation efficiency was measured by ABDA probe under illumination, and the experimental results showed that QCN had a high reactive oxygen species generation efficiency.

Embodiment 3

[0038] Prepare a DMSO stock solution containing 1 mg / mL QCN and store at room temperature in the dark. Human breast cancer cells MCF-7 were seeded in petri dishes at a density of 10 5 / mL, after it adhered to the wall, add different concentrations of QCN (50nM, 100nM, 200nM, 500nM, 1μM, 2μM) and continue to culture for 24h, followed by 532nm laser irradiation for 5min and continue to culture for 24h, then add 20μLMT (5mg / mL), After 4 hours of incubation in a 37°C incubator, the medium was removed, 150 μL of dimethyl sulfoxide was added, and the absorbance value was detected at 570 nm by a microplate reader.

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Abstract

The invention provides an aggregation-induced luminescence photosensitizer based on quinoxalinone skeleton, a preparation method and application thereof. The photosensitizer molecule is composed of o-phenylenediamine and its derivatives through cyclization, nucleophilic substitution and aldol condensation. It is obtained by coupling reaction with Suzuki. The compounds of the present invention have strong near-infrared fluorescence emission in the aggregated state, and at the same time generate a large number of active oxygen radicals under the irradiation of a 530 nm laser, and can be used as potential photosensitizers. The compounds of the present invention can be directly added to the culture medium and then used for photodynamic therapy of tumor cells, and can also be prepared into nanoparticles and then injected intravenously to exert in vivo photodynamic therapy.

Description

technical field [0001] The present invention relates to the field of novel drug development, in particular, to an aggregation-induced luminescence photosensitizer based on quinoxalinone cyanoanthraquinone, and a preparation method and application thereof. Background technique [0002] Photodynamic therapy is a non-surgical method of treating cancer. It uses photosensitizers to absorb photons under light conditions to reach the excited state, and then reach the triplet state through intersystem crossing. The triplet-triplet energy transfer process occurs, and the energy is transferred to oxygen to obtain singlet oxygen to kill cancer cells. Therefore, the design and synthesis of a photosensitizer with excellent performance is particularly important for photodynamic therapy. [0003] Compared with traditional porphyrin-based photosensitizers, porphyrin-based compounds easily form aggregates in the aqueous phase due to their planar rigid structure, induce fluorescence quenching...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/06C09K11/06A61K41/00A61P35/00
CPCC07D409/06C09K11/06A61K41/0057A61P35/00C09K2211/1011C09K2211/1044C09K2211/1092
Inventor 张鹏施雷雷曹伟灵马婧匡海珠
Owner 无锡市觉新生物科技有限公司
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