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AIE type azo enzyme fluorescent small-molecular probe and preparation method thereof

A small molecule probe and azoase technology, applied in the field of fluorescent probes, can solve the problems of single research and lack of application of organic small molecule fluorescent probes, and achieve high luminous efficiency, good fluorescence photostability, and accurate realization. The effect of detection

Active Publication Date: 2022-07-12
YANGZHOU POLYTECHNIC INST
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

However, the relevant research is relatively single, mostly based on the single-molecule fluorescence response of rhodamine and cyanine dyes, while the research based on other molecules is relatively poor---this limits the use of organic small molecule fluorescent probes in anaerobic cancer to a certain extent. Diagnostic Applications

Method used

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  • AIE type azo enzyme fluorescent small-molecular probe and preparation method thereof
  • AIE type azo enzyme fluorescent small-molecular probe and preparation method thereof
  • AIE type azo enzyme fluorescent small-molecular probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] step 1

[0029]

[0030] Under nitrogen protection, compound 4,4'-dibromomethylazobenzene 4g (11mmol) was dissolved in 100ml of trimethyl phosphite, then slowly heated to 150°C and incubated for 36 hours, chromatographic detection tracked the reaction progress, the reaction After the end, the reaction solution was poured into 50 ml of petroleum ether, and a large amount of yellow solid was precipitated, which was extracted under reduced pressure, dried, and recrystallized from methanol to obtain a pale yellow solid ON-1, 4.2 g, yield: 90%. 1 H NMR (300MHz, CDCl 3 ): δ8.96-8.93 (d, J=9.0Hz, 4H), 7.36-7.33 (d, J=9.0Hz, 4H), 3.64 (s, 12H), 3.03 (d, 4H).

[0031] Step 2:

[0032]

[0033] Under nitrogen protection, 4,4'-dibromo-4"-formyltriphenylamine (SX-1, 5.0 g, 9.5 mmol), 3,6-di-tert-butyl-9-hydrocarbazole (KZ-1 , 5.8g, 20.9mmol), cuprous iodide (0.72g, 3.78mmol), 1,10-o-phenanthroline (1.5g, 8.3mmol) and potassium carbonate (3.5g, 20.9mmol) mixture was dissolv...

Embodiment 2

[0038] step 1

[0039]

[0040] Under nitrogen protection, compound SX-1 (2.5 g, 5.8 mmol), Pd (PPh 3 ) 4 (0.022g, 0.18mmol), potassium carbonate (0.85g, 8mmol), SF-1 (3.75g, 13mmol) were dissolved in DMF (80ml), heated at 85°C for 12h; after cooling to room temperature, water (100mL) was added , adjust the pH value to weak acidity with 1N hydrochloric acid, the amount of yellow solid precipitation, and dry in a vacuum drying oven at 50 ° C for 24 hours. Then more stringent purification by column chromatography (eluting with dichloromethane / methanol = 9 / 1) gave SFX-1 as a yellow solid, 2.0 g, yield: 90%. 1 H NMR (CDCl 3 ,ppm):δ9.83(s,1H),7.81-7.78(d,2H,J=9.0Hz),7.72-7.70(d,4H,J=6.0Hz),7.54-7.53(d,2H,J =3Hz), 7.49-7.48(d,2H,J=3Hz), 7.36-7.33(q,4H), 7.21-7.13(d,4H), 7.12-7.08(q,4H).

[0041] Step 2

[0042]

reference example 1

[0043] Reference Example 1, Step 3, yielded a yellow solid, yield: 88%. 1 H NMR (300MHz, CDCl 3 ):8.96-8.93(d,J=9.0Hz,4H),δ7.81-7.78(d,4H,J=9.0Hz),7.72-7.70(d,8H,J=6.0Hz),7.54-7.53( d, 4H, J=3Hz), 7.49-7.48 (d, 4H, J=3Hz), 7.36-7.33 (m, 12H), 7.21-7.13 (d, 8H), 7.12-7.08 (q, 8H).

[0044] Example 2:

[0045] step 1:

[0046]

[0047] Under nitrogen protection, add 4-vinylpyridine (1.0mL, 8mmol), compound SX-1 (1.5g, 3.5mmol), palladium acetate (0.0225g, 0.10mmol), three (o-methylphenyl)phosphine (0.06 g, 0.20 mmol) and anhydrous potassium phosphate (0.7 g, 3 mmol) were heated to 120° C. in an oil bath under magnetic stirring for 24 h. After the reaction, the reaction solution was filtered into anhydrous methanol and suction filtered to obtain an orange-red solid, which was dried in vacuo. The crude product was purified by column chromatography with gradient elution to obtain an orange-red solid BEX-1, 2.25 g, with a yield of 2.25 g. 75%. 1 H NMR (CDCl 3 ,300MHz):δ9.8...

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Abstract

The invention relates to an AIE type azo enzyme fluorescent small-molecular probe and a preparation method thereof, the AIE type azo enzyme fluorescent small-molecular probe is prepared by taking a triphenylamine derivative as a main light-emitting unit and an azo group as a specific recognition group through witting-horner reaction condensation, and the AIE type azo enzyme fluorescent small-molecular probe has the following structural formula: the AIE type azo enzyme fluorescent small-molecular probe with a novel structure is constructed; the prepared hypoxic enzyme probe is good in fluorescence light stability, obvious in hypoxic enzyme selective recognition and strong in anti-interference capability; the probe has obvious absorption signal change and strong AIE fluorescence response for azo reductase in cells, overcomes the problem of high-concentration fluorescence quenching of probe molecules, can realize quantitative detection of hypoxic enzyme in tumor cells, has strong absorption and fluorescence intensity and emission wavelength change response for azo reductase in cells, and can realize quantitative detection of hypoxic enzyme in tumor cells. The accurate detection on the hypoxic enzyme in the tumor cells can be realized.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, in particular to an AIE type azoase fluorescent small molecule probe and a preparation method thereof. Background technique [0002] Fluorescence imaging technology is widely used in cell and living biological imaging analysis due to its advantages of visualization, in situ, and non-destructiveness. Among the commonly used fluorescent probes, small molecule fluorescent probes have attracted much attention due to their advantages of easy synthesis and modification, easy spectral adjustment, high fluorescence quantum yield, and good biocompatibility. [0003] The application of organic fluorescent small molecules in cancer diagnosis has its outstanding advantages. For example, hypoxia is a common phenomenon in most solid tumor cells in cancer cells. Hypoxia can induce accelerated bioreduction reactions and lead to the expression of intracellular reductases. Such as quinone reductase, az...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D213/36C07D333/20C09K11/06G01N21/64
CPCC07D209/86C07D333/20C07D213/36C09K11/06G01N21/6428G01N21/6456C09K2211/1029C09K2211/1088C09K2211/1092Y02E10/549
Inventor 成焕仁范亚骏冷静张培培
Owner YANGZHOU POLYTECHNIC INST
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