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Triphenylamine polypyridine salt based photosensitizer and preparation method and application of triphenylamine polypyridine salt based photosensitizer

A technology of benzothiadiazole, triphenylamine, pyridine, and triphenylamine, which is applied in the field of biomedical engineering, can solve the problems of inability to monitor the cell state in real time, low singlet oxygen quantum yield of photosensitizer, etc., to promote cancer cell death, nuclear The effect of enhanced membrane permeability and simple preparation method

Active Publication Date: 2018-11-02
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The invention solves the technical problem that the singlet oxygen quantum yield of the photosensitizer in the prior art is low and the cell state cannot be monitored in real time

Method used

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  • Triphenylamine polypyridine salt based photosensitizer and preparation method and application of triphenylamine polypyridine salt based photosensitizer
  • Triphenylamine polypyridine salt based photosensitizer and preparation method and application of triphenylamine polypyridine salt based photosensitizer
  • Triphenylamine polypyridine salt based photosensitizer and preparation method and application of triphenylamine polypyridine salt based photosensitizer

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the synthesis of photosensitizer JP2

[0035] (1) Synthesis of compound III

[0036]

[0037] In a 100ml two-necked flask, add triphenylamine monoaldehyde diiodide IV (4.2g, 8mmol), cesium carbonate (5.21g, 16mmol), catalyst tetraphenylphosphine palladium (0.92g, 0.8mmol) and 50ml toluene, nitrogen protection , heated to 60°C, stirred for 10min, injected ethanol dissolved with 4-pyridineboronic acid (2.96g, 24mmol) into the two-necked flask, raised the temperature to 90°C, and refluxed for 10h. After the reaction was completed, it was cooled to room temperature and filtered with celite to remove the catalyst. The filtrate was spin-dried, extracted with ethyl acetate and saturated saline solution, and the crude product was spin-dried for column chromatography (eluent: DCM:Ethanol=50:1). Obtained III, yield: 3.15 g (92%). 1 H NMR (400MHz, cdcl 3 )δ9.87(s,1H),8.66(dd,J=4.5,1.6Hz,4H),7.89–7.71(m,2H),7.68–7.59(m,4H),7.50(dd,J=4.5, 1.6Hz, 4H), 7.37–7.25(...

Embodiment 2

[0044] Example 2: Fluorescence changes of photosensitizer JP2 in different concentrations of ctDNA

[0045] At a concentration of 10 μmol L -1 Different concentrations of ctDNA were added to the PBS solution of photosensitizer JP2. -1 , the excitation wavelength is 445nm, with the increase of ctDNA concentration, the fluorescence intensity is continuously enhanced, such as figure 2 shown. It shows that JP2 and ctDNA have a certain binding ability, which can stimulate the aggregation-induced luminescent performance of JP2 itself, thereby enhancing the fluorescence. This is also the main reason why JP2 lights up the nucleus.

Embodiment 3

[0046] Example 3: Cell death of living HeLa cancer cells under illumination at different times

[0047] After HeLa cells were incubated with 10 μM photosensitizer JP2 for 2 h, the residual dye was washed away with PBS solution and then incubated with mitochondrial dye Mito Tracker Deep Red for 30 min. Observe the fluorescence distribution of the photosensitizer in the cells under a microscope, and under the irradiation of the confocal built-in light source (488nm, 10mW), the obtained image 3 the result of which image 3 (a), image 3 (e) and image 3 (i) are the bright field images of the cells at 0 seconds, 8 seconds and 15 seconds after adding the photosensitizer JP2, respectively; image 3 (b) for, image 3 (f) and image 3 (j) are the fluorescence images of the cells at 0 seconds, 8 seconds and 15 seconds after adding the photosensitizer JP2, respectively; image 3 (c) for, image 3 (g), image 3 (k) are respectively the staining diagrams of mitochondria in the ce...

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Abstract

The invention discloses a triphenylamine polypyridine salt based photosensitizer and a preparation method and an application of the triphenylamine polypyridine salt based photosensitizer, and belongsto the technical field of biomedical engineering. The preparation method comprises enabling triphenylamine monoaldehyde diiodine and 4-pyridineboronic acid to have a coupling reaction, generating triphenylamine monoaldehyde bipyridine, then enabling the triphenylamine monoaldehyde bipyridine and an electron withdrawing group to have a condensation reaction, enabling an obtained product to have a salt forming reaction with iodomethane, and obtaining the photosensitizer. The photosensitizer has the electron withdrawing group, the singlet oxygen is produced efficiently under the illumination condition, the purpose of rapidly efficiently killing a tumor cell is fulfilled; the photosensitizer not only efficiently kills the tumor cell and inhibits the growth of the tumor, but also monitors the death of the tumor cell and a tumor tissue in real time, and therefore, a photosensitizer medicine can be used to judge the effect of the photosensitizer on the tumor cell. The preparation method of the photosensitizer is simple, and the cost is low.

Description

technical field [0001] The invention belongs to the field of biomedical engineering, and relates to a photosensitizer based on triphenylamine polypyridinium salt, a preparation method and application thereof. Background technique [0002] With the continuous improvement of human living standards, people pay more and more attention to health issues. However, the problems that cancer has brought to the health of all mankind have not been resolved, and even become more serious due to the deterioration of the environment and other impacts. Although many researchers are committed to exploring new ways to treat cancer, the most commonly used methods are still traditional methods such as surgery, radiotherapy and chemotherapy. However, these traditional methods have their own disadvantages, such as: surgery cannot completely remove malignant tumors, radiotherapy and chemotherapy will bring huge toxic side effects to the body. In response to these current situations, we urgently n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/38C07D417/14C09K11/06A61K41/00A61K49/00A61P35/00
CPCA61K41/0057A61K49/0032A61P35/00C07D213/38C07D417/14C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1051
Inventor 罗亮高玉婷王修霞何珍艳孟凡玲
Owner HUAZHONG UNIV OF SCI & TECH
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