Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of fluorescent probe with AIE effect and its preparation method and application

A fluorescent probe and effect technology, applied in the field of fluorescent probes, can solve problems such as poor selectivity, poor photobleaching resistance, and high biological toxicity, and achieve the effect of improving the possibility

Active Publication Date: 2019-01-22
GUANGDONG UNIV OF TECH
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention provides a fluorescent probe with AIE effect, which is used to solve the problem that the biological thiol compounds GSH, Cys and Hcy are often difficult to distinguish with existing fluorescent probes due to their structural similarity, and there are options for the detection of biological thiol amino acids. Poor performance, low sensitivity, poor resistance to photobleaching, high biotoxicity, and ACQ effects

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of fluorescent probe with AIE effect and its preparation method and application
  • A kind of fluorescent probe with AIE effect and its preparation method and application
  • A kind of fluorescent probe with AIE effect and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] With a double-necked flask, 2.0004g (8.1mmol) of 1-pyrene boronic acid, 3.0000g (8.95mmol) of triphenylbromoethylene and 0.5000g K 2 CO 3 dissolved in 40 mL of ethylene glycol dimethyl ether and 20 mL of H 2 O after N 2 Under protection, 0.1400 g (0.12 mmol) of tetrakistriphenylphosphine palladium was added, and heated to reflux at 40-60° C. for 15-20 h. Ethylene glycol dimethyl ether was removed by a rotary evaporator and filtered under reduced pressure to obtain a green crude product. Chromatography with n-hexane: ethyl acetate = 8:1 as the eluent gave 1-(1,2,2-triphenylethenyl)pyrene as a blue-green powdery solid with a yield of 36.21%.

[0051] 1-(1,2,2-triphenylethenyl)pyrene's proton nuclear magnetic resonance spectrum measurement results are: 1H NMR (400MHz, DMSO-d6) δ = 8.35 (d, 1H, J = 8Hz), 8.27 (d ,1H,J=8Hz), 8.22(d,1H,J=8Hz), 8.15(m,5H), 7.89(d,1H,J=8Hz), 7.27(m,5H), 7.06(m,5H) , 6.98 (d, 2H, J=8Hz), 6.88 (m, 3H).

Embodiment 2

[0053]Dissolve 0.2740g (0.6mmol) of 1-(1,2,2-triphenylethenyl)pyrene in 5mL of dichloromethane, heat and stir until clear, and slowly add 100μL65 diluted with 0.2mL acetic acid dropwise under ice bath %-68% mixed solution of nitric acid. After 1 to 2 hours, heat and reflux for 4 to 5 hours. After the reaction reaches the limit as detected by TLC, use saturated NaHCO 3 Extract, filter under reduced pressure, and spin dry the solvent. The compound of formula (Ⅲ) was obtained as a yellow solid by column chromatography with the eluent of n-hexane:dichloromethane=2:1, specifically 1-nitro-8-(1,2,2-triphenyl A mixture of vinyl)pyrene and 1-nitro-6-(1,2,2-triphenylethenyl)pyrene with a yield of 85.01%.

Embodiment 3

[0055] 0.5000g (1mmol) of 1-nitro-8-(1,2,2-triphenylvinyl)pyrene and 1-nitro-6-(1,2,2-triphenyl) prepared in Example 2 The mixture of vinyl vinyl)pyrene was dissolved in 10mL of toluene:ethanol=1:1 mixed solvent, under N 2 Add 0.0800g (0.75mmol) of 10% Pd / C under protection, and slowly add 0.0600g (1.2mmol) of hydrazine hydrate dropwise after heating to reflux. After reacting for 4 to 5 hours, no raw materials were detected by TLC, and then filtered under reduced pressure, and the solvent was removed by rotary evaporation, and the compound of formula (II) was obtained as a yellow solid by column chromatography with the polarity of n-hexane: ethyl acetate = 3:1 8-(1,2,2-triphenylethenyl)pyrene-1-amine, the yield rate is 23.69%; Vinyl)pyrene-1-amine, the yield was 30.18%.

[0056] 8-(1,2,2-triphenylethenyl)pyrene-1-amine H NMR spectrum measurement results are: 1 HNMR (400MHz, DMSO-d6) δ = 8.16 (d, 1H, J = 12Hz), 8.02 (d, 1H, J = 8Hz), 7.94 (d, 1H, J = 8Hz), 7.84 (d, 2H, J = ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the field of fluorescent probes and in particular relates to a fluorescent probe with an AIE (Aggregation-Induced Emission) effect as well as a preparation method and application thereof. The invention provides the fluorescent probe with the AIE effect; an experiment result shows that the fluorescent probe with the AIE effect can be used for sensitively detecting a biological mercapto molecule, has strong fluorescence response on cysteine (Cys) and homocysteine (Hcy), but has no response on glutathione (GSH); the problem that the similarity of structures of the GSH, the Cys and the Hcy in a biological mercapto compound is difficult to distinguish by an existing fluorescent probe is solved. Moreover, the fluorescent probe with the AIE effect can be used for solvingan ACQ (Aggregation-Caused Quenching) effect caused by poor water solubility.

Description

technical field [0001] The invention belongs to the field of fluorescent probes, in particular to a fluorescent probe with AIE effect and its preparation method and application. Background technique [0002] Biosulfhydryl groups, including glutathione (GSH), cysteine ​​(Cys) and homocysteine ​​(Homocysteine, Hcy), are involved in many physiological processes such as regulation of redox balance, detoxification, regulation of metabolic enzymes It plays a key role in the active site of cofactors. However, how to efficiently and quickly detect sulfhydryl compounds in organisms is a major problem to be solved in the fields of chemistry and biology. [0003] Biothiol compounds GSH, Cys, and Hcy play different roles in living organisms, for example, a lack of cysteine ​​can lead to lethargy, slow growth, and liver damage, and high levels of homocysteine ​​may induce Alzheimer's disease , cardiovascular disease, and coronary heart disease. Glutathione is also essential as a precu...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/448C09K11/06G01N21/64
CPCC07D207/448C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029G01N21/6428
Inventor 董方帝籍少敏赖辉燕陈华慧霍延平
Owner GUANGDONG UNIV OF TECH