Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Fluorescent probe for detecting biological mercaptan in water-soluble environment and preparation method and application thereof

A technology of fluorescent probes and biothiols, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of complex synthesis process, low sensitivity, long response time, etc., and achieve high detection sensitivity and selectivity High and simple preparation method

Inactive Publication Date: 2019-08-16
SHANXI UNIV
View PDF2 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, many of them have long response time, low sensitivity, complicated synthesis process or require short UV light excitation

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 for detecting biological mercaptan in water-soluble environment and preparation method and application thereof
  • Fluorescent probe for detecting biological mercaptan in water-soluble environment and preparation method and application thereof
  • Fluorescent probe for detecting biological mercaptan in water-soluble environment and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: the preparation of compound 1:

[0029] N-diethylaminophenol (1.8 g, 10.9 mmol) and phthalic anhydride (1.8 g, 12.2 mmol) were reacted in 200 mL benzene at 130 ° C for 12 hours to obtain a white solid, and then the white solid (0.626 g , 2 mmol) into 10 mL of methanesulfonic acid containing p-hydroxyacetophenone (0.272 g, 2 mmol), react at 90 °C for 8 hours, add to 200 mL of ice water after cooling, add 10 mL of perchloric acid, and dichloro After extraction with methane (50 mL × 3), drying and rotary evaporation to dry the solvent, compound 1 was obtained by column chromatography with a mixed solvent of dichloromethane and glacial acetic acid, yield: 33%. Synthetic route such as figure 1 shown.

Embodiment 2

[0030] Embodiment 2: Preparation of fluorescent probes for detecting biothiols in water-soluble environments according to the present invention:

[0031] Compound 1 (600 mg, 1.45 mmol), 2,4-dinitrobenzenesulfonyl chloride (1.542 g, 5.8 mmol), triethylamine (804 μL, 5.8 mmol) were dissolved in 30 mL redistilled dichloromethane, ice After bathing for 1 hour, return to room temperature and stir for 16 hours. Diluted with 30 mL of dichloromethane, washed with water (50 mL × 3), dried and evaporated to dryness, and separated by column chromatography with a mixed solvent of dichloromethane and methanol to obtain the target compound PA-SN, yield: 50%. 1 H NMR (600 MHz, CDCl 3 ) δ( ppm ) :8.68 (d, J = 1.8 Hz, 1H), 8.52 (dd, J = 8.6, 1.9 Hz, 1H), 8.41 (s, 2H), 8.21(d, J = 8.6 Hz, 1H), 7.99 (d, J = 7.7 Hz, 1H), 7.84 (d, J = 8.7 Hz, 2H), 7.67(t, J = 7.5 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 6.63 (d, J = 8.9 Hz, 1H), 6.47(dd, J = 18.9, 10.0 Hz, 2H), 5.65 (s, 1H), 5.32 (s, ...

Embodiment 3

[0032] Embodiment 3: titration experiment of pH=7.4 fluorescent probe and biothiol:

[0033] In the PBS buffer solution with pH=7.4, add the fluorescent probe with an initial concentration of 2 mM, so that the concentration of the fluorescent probe in the solution is 10 μM. Then, different amounts of biothiols with an initial concentration of 20 mM were added sequentially, so that the concentrations of biothiols in the solution were 2 μM, 4 μM, 6 μM, 8 μM, 10 μM, 12 μM, 14 μM, and 16 μM, respectively. , 18 μM, 20 μM, 24 μM, 28 μM, 32 μM, 36 μM, 40 μM, 45 μM, 50 μM, 60 μM, 80 μM, 100 μM, 120 μM, 140 μM, 160 μM, 180 μM, 200 μM, 250 μM, 300 μM, 500 μM, without adding biothiol as a control, let stand for 0.5 hours to fully react biothiol and fluorescent probe. The absorption and fluorescence spectra of different biological thiols were tested with an absorption spectrometer and a fluorescence spectrometer respectively. The excitation wavelength of the fluorescence spectrum was 570...

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 technical field of organic small molecule fluorescent probes, and provides a fluorescent probe for detecting biological mercaptan in a water-soluble environment and a preparation method and application thereof. The molecular formula of the fluorescent probe is C32H26N3O10S<+>, the name of the probe compound is 4-(2-carboxyphenyl)-7-(diethylamino)-2-(4-(((2,4-dinitrophenyl) sulfonyl) oxy) phenyl) benzopyran, which is abbreviated as PA-SN, and the structural formula is shown in the specification. The preparation method of the fluorescent probe is simple. The probe has large fluorescence enhancement multiple and obvious color change, and can recognize the biological mercaptan with high selectivity in a water system, an organic solvent system and organisms. The fluorescence of the probe is weak and almost colorless in the organic system. After the probe is reacted with the biological mercaptan, the fluorescence of a solution increases significantly, and the color changes to purple obviously. The detection of the biological mercaptan is highly selective, sensitive and obvious.

Description

technical field [0001] The invention belongs to the technical field of organic small molecule fluorescent probes, in particular to a fluorescent probe for detecting biothiols in a water-soluble environment and its preparation method and application. The fluorescent probe can be used in water-soluble, organic environments and cell environments Efficient identification of biothiols. Background technique [0002] Biothiols such as cysteine ​​(Cys), homocysteine ​​(Hcy) and glutathione (GSH) play key roles in biological systems, and abnormal levels of these biothiols are associated with many diseases. Cys deficiency is associated with many syndromes such as slow growth in children, hair depigmentation, edema, lethargy, liver damage, muscle and fat loss, skin damage and weakness. GSH deficiency is also implicated in many diseases such as liver damage, loss of white blood cells, cancer, AIDS and neurodegenerative diseases. Therefore, rapid, convenient, selective and sensitive de...

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
IPC IPC(8): C07D493/10C09K11/06G01N21/64
CPCC07D493/10C09K11/06C09K2211/1007C09K2211/1088G01N21/6428
Inventor 李亚平乔柳琪蔡建华吕鑫
Owner SHANXI UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com