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Aggregation-induced emission photosensitizer, preparation method and application

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

Active Publication Date: 2021-06-22
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 emission photosensitizer, preparation method and application
  • Aggregation-induced emission photosensitizer, preparation method and application
  • Aggregation-induced emission photosensitizer, preparation method and application

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Embodiment 1

[0034] This embodiment relates to a kind of quinoxalinone derivative, and its preparation method is as follows: O-phenylenediamine (0.1mol, 10.8g) is dispersed in absolute ethanol (150mL), and ethyl pyruvate (0.12 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 a white powder 1a, (13.6g, yield 86%); 1a (20mmol, 3.2g), K 2 CO 3 (24mmol, 3.31g) was dispersed in acetone, and then bromopropene (24mmol, 3.67g) was added dropwise under stirring, the reaction mixture was reacted overnight at 62°C, the solvent was evaporated to dryness, the residue was added to water and ethyl acetate, separated The ethyl acetate phase was separated on a silica gel column (petroleum ether: ethyl acetate = 10:1), and purified to obtain 3.0 g of 1b with a yield of 54%. Suspend 1b (2mmol, 500mg) in acetic acid, add 5-bromothiophene-2-carbaldehyde (3mmol, 570mg) and a catalytic amount of concentra...

Embodiment 2

[0037] Configure 1mg / mL QCN stock solution in DMSO, and then pass through different ratios of DMSO / H 2 The mixed solvent of O dilutes QCN to 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 a steady-state time-resolved fluorescence spectrophotometer, and it was found that the maximum emission wavelength of QCN reached 800nm. Then the active oxygen generation efficiency was measured by ABDA probe under light, and the experimental results showed that QCN had a high active oxygen generation efficiency.

Embodiment 3

[0039]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 culture dishes at a density of 10 5 / mL, after it adheres to the wall, add different concentrations of QCN (50nM, 100nM, 200nM, 500nM, 1μM, 2μM) and continue to culture for 24h, then continue to culture for 24h after 532nm laser irradiation for 5min, then add 20μL MTT (5mg / mL), After incubating in a 37 °C incubator for 4 h, 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 emission photosensitizer based on a quinoxaline ketone skeleton, and a preparation method and application thereof. A photosensitizer molecule is prepared from o-phenylenediamine and a derivative thereof through cyclization, nucleophilic substitution, aldol condensation and Suzuki coupling reaction. The compound provided by the invention has strong near-infrared fluorescence emission in an aggregation state, generates a large amount of reactive oxygen free radicals under the radiation of a 530 nm laser, and can be used as a potential photosensitizer. The compound provided by the invention can be directly added into a culture medium for photodynamic therapy of tumor cells, and can also be prepared into nano particles for intravenous injection to perform in-vivo photodynamic therapy.

Description

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

Claims

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Application Information

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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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