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

Fluorescent probes based on rhodamine-coumarin derivatives, and preparation method and application of fluorescent probes

A technology of coumarin derivatives and fluorescent probes, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as decreased arterial elasticity, elevated cholesterol, and elevated blood pressure, achieving strong selectivity, The effect of high sensitivity and easy availability of raw materials

Inactive Publication Date: 2017-11-07
HENAN POLYTECHNIC UNIV
View PDF1 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, if the metabolic balance of copper ions in the body is disrupted, it may cause metabolic disorders and many diseases, such as elevated cholesterol, decreased arterial elasticity, and increased blood pressure

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 probes based on rhodamine-coumarin derivatives, and preparation method and application of fluorescent probes
  • Fluorescent probes based on rhodamine-coumarin derivatives, and preparation method and application of fluorescent probes
  • Fluorescent probes based on rhodamine-coumarin derivatives, and preparation method and application of fluorescent probes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of Rhodamine-Coumarin Derivatives

[0027]

[0028] Dissolve 0.246g of 7-hydroxy-3-acetoacetylcoumarin in 10mL of acetonitrile, then add 0.428g of rhodamine 6G hydrazide, and stir under reflux for 3 hours under normal pressure. After cooling to room temperature, a large amount of solids are precipitated, and filtered under reduced pressure. The filter residue was recrystallized with acetonitrile to obtain a yellow solid, which was the target product, and the yield of the target product was 58.2%.

[0029] Rhodamine-coumarin derivative NMR analysis results are as follows:

[0030] Single crystal structure: the crystal structure of rhodamine-coumarin derivatives is shown in figure 1 ;

[0031] Proton NMR spectrum: 1 H NMR (400MHz, DMSO-d 6 ),δ(ppm):11.67(s,1H,OH), 10.89(s,1H,NH),8.41(s,1H,Aryl-H),7.88-7.90(d,1H,Aryl-H),7.56 -7.68(m,3H, Aryl-H),7.09-7.11(d,1H,Aryl-H),6.75-6.78(dd,1H,Aryl-H),6.67-6.68(d,1H,Aryl-H) ,6.19-6.22(d,4H,Aryl-H),6.10(s,1H,CH),5.1...

Embodiment 2

[0034] Determination of Optical Properties of Rhodamine-Coumarin Derivatives on Divalent Copper Ions

[0035] The rhodamine-coumarin derivatives prepared in the above-mentioned Example 1 are used as probes in acetonitrile / water (volume ratio 9: 1) medium to prepare a molar concentration of 5 × 10 -6 mol / L solution, respectively, at a molar concentration of 1×10 -5 mol / L Ag + , Al 3 + , Ca 2+ , Cd 2+ ,Co 2+ , Cr 3+ , Cu 2+ , Fe 3+ , Hg 2+ , K + , Mg 2+ ,Mn 2+ , Na + , Ni 2+ , Pb 2+ , Zn 2+ Add an equal amount of the above-mentioned probe solution in the solution of metal ions, and use a fluorescence spectrometer to carry out fluorescence emission spectrum analysis on the rhodamine-coumarin derivatives prepared in Example 1. The excitation wavelength is 350nm, and the resulting fluorescence emission spectrum See Figure 4. The rhodamine-coumarin derivatives prepared in Example 1 of the present invention interact with divalent copper ions, and the emission pea...

Embodiment 3

[0037] The concentration is 5×10 -6 The rhodamine-coumarin derivatives of mol / L were added to the acetonitrile / water (volume ratio 9:1) solution as the fluorescent probe with a concentration of 0mol / L, 5×10 -7 mol / L, 1×10 -6 mol / L, 1.5×10 -6 mol / L, 2×10 - 6 mol / L, 2.5×10 -6 mol / L, 3×10 -6 mol / L, 3.5×10 -6 mol / L, 4×10 -6 mol / L, 4.5×10 -6 mol / L, 5×10 -6 mol / L and 1×10 -5 The divalent copper ion of mol / L adopts fluorescence spectrometer to carry out fluorescence emission spectrum analysis to it respectively, records the emission intensity value at 555nm place, and the emission spectrum figure of gained is shown in Figure 5 . by attaching Figure 5 It can be seen that as the concentration of copper ions increases, the fluorescence intensity of the rhodamine-coumarin derivative fluorescent probe at 555nm is gradually enhanced, and the intensity of the absorption peak is correlated with the concentration of copper ions at 0-5×10 -6 Linear correlation in the range of mo...

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 present invention provides a fluorescent probe based on rhodamine-coumarin derivatives and its preparation method and application, wherein the chemical structural formula of the rhodamine-coumarin derivatives is as follows: Rhodamine-coumarin of the present invention Derivatives can selectively interact with divalent copper ions, changing from weak fluorescence to yellow fluorescence, and have a colorimetric fluorescence enhancement effect, which can realize naked eye discrimination detection, especially as a fluorescent probe for the convenient detection of intracellular copper ions .

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a fluorescent probe based on rhodamine-coumarin derivatives and a preparation method and application thereof. Background technique [0002] Copper is an important trace element in the human body, and it plays a very important role in different physiological processes such as mitochondrial respiration, iron absorption, and enzyme redox. However, if the metabolic balance of copper ions in the body is destroyed, it may cause metabolic disorders and many diseases, such as elevated cholesterol, decreased arterial elasticity, and elevated blood pressure. In addition, copper has also become an important metal pollutant due to the large amount of copper ions mined and widely used. In view of its importance to life and the environment, scientists have been working on the detection of copper ions in biological and environmental systems using selective colorimetric and fluorescent sensing ...

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): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/6402
Inventor 王元吴伟娜李慧军吴浩
Owner HENAN POLYTECHNIC 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