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

A kind of benzothiazole derivative and its preparation method and application

A technology of benzothiazole and derivatives, applied in the field of heterocyclic compounds and fluorescent probes, can solve the problems of rare probes and few reports, achieve good cell membrane penetration, reduce interference, and reduce errors

Active Publication Date: 2022-03-18
SHANXI UNIV
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the pH of subcellular compartments such as cytoplasmic matrix, nucleus, and mitochondria in a large number of cells is nearly neutral or weakly alkaline. There are not many reports on this kind of pH probes, especially the probes based on ratiometric fluorescence emission technology. is rare

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 benzothiazole derivative and its preparation method and application
  • A kind of benzothiazole derivative and its preparation method and application
  • A kind of benzothiazole derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Preparation of 1,6-(2-(benzothiazol-2-yl)vinyl)naphthalene-2-ol (BTNO):

[0027]

[0028] (1) 6-hydroxy-2-naphthaldehyde (10mmol, 1.7218g), 2-methylbenzothiazole (15mmol, 1.89mL), trimethylchlorosilane (50mmol, 6.40mL), 10mL CH2Cl2 mixed The solution was reacted in a high-pressure reactor at 105°C for 24h. The solvent was removed under reduced pressure, and the resulting solid was dissolved in water and washed with Na 2 CO 3 Adjust the pH of the solution to 6.0 with CH 2 Cl 2 extraction. Remove the solvent to obtain the product crude product;

[0029] (2) the product crude product is separated and purified through a silica gel column, v 乙酸乙酯 :v 正己烷 =1:6 was the eluent, and the product BTNO (1.58 g, 52%) was obtained as a reddish-brown solid. 1 H NMR(400MHz,DMSO)δ10.62(s,1H),10.34(s,1H),10.04(s,1H),9.97(s,1H),9.65(s,1H),8.43(s,1H) ,8.02(d,J=8.7Hz,2H),7.80(dd,J=18.1,8.5Hz,2H),7.21(d,J=8.4Hz,2H),7.02(s,1H). 13 C NMR (101MHz, d 6 -DMSO)δ197.80(s), 197.53(s), 1...

Embodiment 2

[0031] The BTNO concentration of Example 1 is maintained at 150 μM, and the pH value is adjusted with high-concentration and small-volume HCl and NaOH solutions in the DMSO / water (volume ratio is 2:1) system, and its absorption spectrum is recorded ( figure 1 ). With the decrease of pH value, the absorption peak at 385nm decreases gradually, the absorption peak at 321nm increases correspondingly, and there is an isosbestic point at 349nm. The color of the solution also changed from yellow to light green ( figure 2 ).

Embodiment 3

[0033] The BTNO concentration of Example 1 was kept at 10 μM, and the pH value was adjusted with high-concentration and small-volume HCl and NaOH solutions in the DMSO / water (volume ratio: 2:1) system, and the fluorescence emission was recorded at 349 nm as the excitation wavelength. spectrum( image 3 ). With the decrease of pH value, the fluorescence peak at 526nm weakens gradually, while the fluorescence peak at 456nm increases gradually. The color of the solution changed from green to blue ( Figure 4 ). Fitting F via the Boltzmann function 456nm / F 526nmValue vs. pH change curve, calculate pK a The value is 7.91±0.034 ( Figure 5 ), the pH response linear range is 7.00-9.50. The linear regression equation is F 456nm / F 526nm =2.13641-0.21119×pH, correlation coefficient R 2 =0.9995( Image 6 ).

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 discloses a benzothiazole derivative, a preparation method and application thereof. The specific name of the derivative is 6-(2-(benzothiazol-2-yl)vinyl)naphthalene-2-phenol (BTNO). Its preparation method: dissolve 6-hydroxy-2-naphthalene formaldehyde and 2-methylbenzothiazole in a small amount of dichloromethane, add trimethylchlorosilane, and heat the reaction to obtain the crude product; remove the solvent from the crude product, and pass through The pure product was obtained by silica gel column separation. As the pH decreases from 11.50 to 4.00, the fluorescence spectrum of BTNO appears blue-shifted, showing a ratio fluorescence emission (F 456nm / F 526nm ) characteristics, and at the same time have the advantages of high sensitivity to pH response, good selectivity, high quantum yield and large Stokes shift. In addition, BTNO, as a probe permeable to the cell membrane, can be used to monitor pH fluctuations in the cytoplasmic range.

Description

technical field [0001] The invention relates to a heterocyclic compound and a fluorescent probe, specifically a benzothiazole derivative (BTNO) and a preparation method thereof, as well as the application of the derivative in monitoring changes in cytoplasmic pH. Background technique [0002] Intracellular pH is one of the important parameters of cell metabolism and plays a very important role in various physiological and pathological processes of cells, such as regulation of enzyme activity, maintenance of protein shape, cell division and apoptosis, ion transport, endocytosis Function, cellular energy generation and conversion, membrane potential balance and information transmission, etc. At the same time, studies have shown that the growth and metastasis of cancer (tumor cells), multidrug resistance, Parkinson's disease, Alzheimer's disease and other diseases are closely related to abnormal intracellular pH. Therefore, real-time and accurate monitoring of intracellular pH...

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): C07D277/64C09K11/06G01N21/64
CPCG01N21/6486C09K11/06C07D277/64C09K2211/1011C09K2211/1037
Inventor 林博樊丽贾晶黄文成双少敏董川
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