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Fluorescent molecular probe for near-infrared photodynamic linkage detection of nitroreductase and hydrogen peroxide as well as preparation method and application of fluorescent molecular probe

A fluorescent molecular probe, near-infrared light technology, applied in chemical instruments and methods, fluorescence/phosphorescence, organic chemistry, etc., can solve problems such as disadvantage and lack of causal linkage analysis technology

Active Publication Date: 2022-08-02
伊明泰(山东)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

And for NTR with H 2 o 2 The causal linkage analysis technology is even more lacking
This is very unfavorable for monitoring the cancer environment and developing prodrugs for precision medicine

Method used

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  • Fluorescent molecular probe for near-infrared photodynamic linkage detection of nitroreductase and hydrogen peroxide as well as preparation method and application of fluorescent molecular probe
  • Fluorescent molecular probe for near-infrared photodynamic linkage detection of nitroreductase and hydrogen peroxide as well as preparation method and application of fluorescent molecular probe
  • Fluorescent molecular probe for near-infrared photodynamic linkage detection of nitroreductase and hydrogen peroxide as well as preparation method and application of fluorescent molecular probe

Examples

Experimental program
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Embodiment 1

[0063] A preparation method of a fluorescent molecular probe for near-infrared photodynamic linkage detection of nitroreductase and hydrogen peroxide, refer to figure 1 , including the following steps:

[0064] Synthesis of compound 7: 3.92g (20.6mmol) of 4-(4-hydroxyphenyl)cyclohexanone, 5.52g (25.7mmol) of p-nitrobenzyl bromide and 5.74g (41.6mmol) of potassium carbonate were dissolved in 80ml of acetone , refluxed at 60 °C for 18 h to obtain a yellow solid crude product. The solid was washed with ethyl acetate / dichloromethane (volume ratio 3:1), and concentrated by rotary evaporation to obtain a yellow solid. Recrystallized with petroleum ether, and distilled under reduced pressure to a yellow solid (NMR such as image 3 shown).

[0065] Synthesis of compound 8: DMF (15 mL) after dehydration and deoxygenation was mixed with CH 2 Cl 2 (15 mL) was placed in a single-neck round bottom flask and stirred in a cold trap (-10°C). Phosphorus oxychloride (11.5 g, 75 mmol) was ...

Embodiment 2

[0070] A preparation method of a fluorescent molecular probe for near-infrared photodynamic linkage detection of nitroreductase and hydrogen peroxide, comprising the following steps:

[0071] Synthesis of compound 7: Dissolve 20.6mmol of 4-(4-hydroxyphenyl)cyclohexanone, 20.6mmol of p-nitrobenzyl bromide and 20.6mmol of sodium carbonate in 80ml of acetone, reflux at 65°C for 16h to obtain a crude yellow solid. product. The solid was washed with ethyl acetate / dichloromethane (volume ratio 3:1), and concentrated by rotary evaporation to obtain a yellow solid. It was recrystallized from petroleum ether and distilled under reduced pressure to a yellow solid.

[0072] Synthesis of compound 8: DMF (15 mL) after dehydration and deoxygenation was mixed with CH 2 Cl 2 (45 mL) was placed in a single-neck round bottom flask and stirred in a cold trap (-8°C). Phosphorus oxychloride (75 mmol) was dissolved in dichloromethane (20 mL) and slowly dropped into the above round bottom flask,...

Embodiment 3

[0077] A preparation method of a fluorescent molecular probe for near-infrared photodynamic linkage detection of nitroreductase and hydrogen peroxide, comprising the following steps:

[0078] Synthesis of compound 7: Dissolve 20.6 mmol of 4-(4-hydroxyphenyl) cyclohexanone, 20.6 mmol of p-nitrobenzyl bromide and 20.6 mmol of sodium carbonate in 80 ml of acetone, and reflux at 55°C for 20 h to obtain a crude yellow solid. product. The solid was washed with ethyl acetate / dichloromethane (volume ratio 3:1), and concentrated by rotary evaporation to obtain a yellow solid. It was recrystallized from petroleum ether and distilled under reduced pressure to a yellow solid.

[0079] Synthesis of compound 8: DMF (15 mL) after dehydration and deoxygenation was mixed with CH 2 Cl 2 (45 mL) was placed in a single-neck round bottom flask and stirred in a cold trap (-6°C). Phosphorus oxychloride (50 mmol) was dissolved in dichloromethane (20 mL) and slowly dropped into the above round bot...

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Abstract

The invention discloses a fluorescent molecular probe for near-infrared photodynamic linkage detection of nitroreductase and hydrogen peroxide as well as a preparation method and application of the fluorescent molecular probe. The structural formula of the fluorescent molecular probe is shown in the specification. The near-infrared fluorescent molecular probe (CNH) provided by the invention can realize visual monitoring on a cell hypoxia environment and a reoxidation process thereof, and the specific process is as follows (referring to an attached drawing 2 in the specification): under the action of a hypoxia marker nitroreductase, firstly, fluorescence is triggered from a closed state; the fluorescence is gradually enhanced along with the aggravation of the hypoxia degree; when reoxidation occurs, a fluorescence product triggered by nitroreductase (NTR) can react with H2O2 generated by reoxidation, so that fluorescence enhancement is caused in another fluorescence channel, and an enhanced ratio signal is generated to reveal the hypoxia reoxidation phenomenon in a life system.

Description

technical field [0001] The present invention relates to cancer cell NTR and H 2 O 2 The field of linkage detection, in particular, relates to a fluorescent molecular probe for linkage detection of nitroreductase and hydrogen peroxide with near-infrared photodynamic linkage, and a preparation method and application thereof. Background technique [0002] The information disclosed in this Background of the Invention is only for enhancement of understanding of the general background of the invention and should not necessarily be taken as an acknowledgement or any form of suggestion that this information forms the prior art already known to a person of ordinary skill in the art. [0003] intracellular H 2 O 2 It plays an important messenger role in regulating growth, proliferation, differentiation, biosynthesis and apoptosis. Excess H 2 O 2 May cause oxidative damage to nucleic acids, alter protein structure, and attack lipid molecules. Therefore, H 2 O 2 It is considere...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/025C09K11/06G01N21/6428G01N21/6458C09K2211/1029C09K2211/1007C09K2211/1014G01N2021/6432Y02P20/55
Inventor 陈光苏东亮毕繁荣
Owner 伊明泰(山东)生物科技有限公司
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