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

Fluorescent probe, preparation method and application based on phenylselenide group specific response to cys

A fluorescent probe and ether-based technology, which is applied in the field of fluorescent probes, achieves the effects of simple synthesis method, obvious detection signal and convenient operation

Active Publication Date: 2021-04-20
上海安能健生物医药科技有限公司
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of phenylselenide as a detection group to utilize the strong nucleophilicity of sulfhydryl groups has very few reports on active sulfides, especially the probes that specifically recognize Cys have not yet been reported.

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
  • Fluorescent probe, preparation method and application based on phenylselenide group specific response to cys
  • Fluorescent probe, preparation method and application based on phenylselenide group specific response to cys
  • Fluorescent probe, preparation method and application based on phenylselenide group specific response to cys

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The preparation steps of the probe are as follows:

[0039] (1) Preparation of compound 1

[0040]

[0041] N 2 Under the protection of the ice-water bath, sodium hydride was added to the tetrahydrofuran solvent and mixed to obtain a mixed solvent, and acetonyl p-toluenesulfonate oxime ester and p-methoxystyryl methyl ketone were dissolved in the mixed solvent according to the ratio of 1:2 equivalent, Reacted at 50°C for 4 hours, quenched with ice water, extracted with dichloromethane, and separated by column chromatography to obtain compound 1;

[0042] 1 H NMR (400 MHz, DMSO) δ 10.70 (s, 1H), 7.35 (d, J = 8.4 Hz, 2H), 6.89 (d, J = 8.6 Hz, 2H), 6.76 (q, J = 16.5 Hz, 2H), 6.54 (s, 1H), 6.02 (s,1H), 3.75 (s, 3H), 2.01 (s, 3H).

[0043] (2) Preparation of Compound 2

[0044]

[0045] Dissolve compound 1 in tetrahydrofuran, add N,N-diisopropylethylamine and triphosgene or thiophosgene at an equivalent ratio of 1:1, stir at 25°C for 1 h, then remove the solv...

Embodiment 2

[0055] The preparation steps of the probe are as follows:

[0056] (1) Preparation of Compound 1

[0057] N 2 Under the protection of the ice-water bath, sodium hydride was added to the tetrahydrofuran solvent and mixed to obtain a mixed solvent, and acetonyl p-toluenesulfonate oxime ester and p-methoxystyryl methyl ketone were dissolved in the mixed solvent according to the ratio of 1:2.5 equivalent, Reacted at 50°C for 4 hours, quenched with ice water, extracted with dichloromethane, and separated by column chromatography to obtain compound 1;

[0058] (2) Preparation of compound 2

[0059] Dissolve compound 1 in tetrahydrofuran, add N,N-diisopropylethylamine and triphosgene or thiophosgene at an equivalent ratio of 1:1.3, stir at 25°C for 1-1.5h, and then remove the solvent under reduced pressure, Compound 2 was obtained by column chromatography separation;

[0060] (3) Preparation of compound 3

[0061] Dissolve compound 2 in dichloromethane, add 1.5 equivalents of ph...

Embodiment 3

[0065] The preparation steps of the probe are as follows:

[0066] (1) Preparation of Compound 1

[0067] N 2 Under the protection of the ice-water bath, sodium hydride was added to the tetrahydrofuran solvent and mixed to obtain a mixed solvent, and acetonyl p-toluenesulfonate oxime ester and p-methoxystyryl methyl ketone were dissolved in the mixed solvent according to the ratio of 1:3 equivalent, Reacted at 50°C for 4 hours, quenched with ice water, extracted with dichloromethane, and separated by column chromatography to obtain compound 1;

[0068] (2) Preparation of Compound 2

[0069] Dissolve compound 1 in tetrahydrofuran, add N,N-diisopropylethylamine and triphosgene or thiophosgene at an equivalent ratio of 1:1.5, stir at 25°C for 1.5h, then remove the solvent under reduced pressure, column layer Analysis and separation obtained compound 2;

[0070] (3) Preparation of compound 3

[0071] Dissolve compound 2 in dichloromethane, add 1.5 equivalents of phosphorus ox...

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 provides a fluorescent probe based on a phenylselenide group that specifically responds to Cys, a preparation method and an application. The probe selects BODIPY dye as the fluorophore, and phenylselenide as the recognition group. The detection mechanism is that Cys undergoes a nucleophilic substitution-rearrangement reaction with phenylselenide, causing a change in fluorescence signal. The above probes detect Cys by ultraviolet and fluorescence spectrometers without interference from other amino acids and reactive oxygen species. The detection process is simple, rapid and sensitive, and the detection limit is 33 nM. More importantly, the probe can detect Cys in cells, and has good application prospects in the field of biological monitoring.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to a fluorescent probe based on a phenyloselenide group that specifically responds to Cys, a preparation method and an application. Background technique [0002] Biosulfide plays an important role in the metabolism of animals, plants and microscopic organisms, food processing and so on. Small molecule thiols are part of biosulfides which include: cysteine ​​(Cys), homocysteine ​​(Hcy) and glutathione (GSH). Abnormal concentrations of the three thiols may lead to various diseases, such as liver damage, cardiovascular disease, Alzheimer's disease, cancer, etc. In animals, cysteine ​​(Cys) is a proteinogenic, semi-essential amino acid that stabilizes protein structure, increases protein rigidity, and regulates protein function by providing disulfide bonds in folded proteins. The precursor of Cys synthesis is Hcy, methionine is converted into homocysteine, and then combined with serine to form a...

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): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1007C09K2211/1055G01N21/6428G01N21/6458G01N2021/6432G01N2021/6439
Inventor 张健赵伟利陶远芳王楠楠王瀚岳金磊苏慧慧
Owner 上海安能健生物医药科技有限公司