Chemiluminiscence substrate with high luminescence intensity, long wavelength and good stability and preparation method and application of chemiluminiscence substrate

A chemiluminescence, high-intensity technology, used in chemiluminescence/bioluminescence, chemical instruments and methods, and analysis by chemically reacting materials, etc., can solve the problem of structural instability, susceptibility to environmental interference, and low probe luminescence intensity. and other problems, to achieve the effect of enhancing chemiluminescence intensity, excellent stability and high intensity

Pending Publication Date: 2020-02-18
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, under physiological conditions, the 1,2-dioxane structure is not stable, so the probe has low luminescence intensity and is susceptible to en

Method used

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  • Chemiluminiscence substrate with high luminescence intensity, long wavelength and good stability and preparation method and application of chemiluminiscence substrate
  • Chemiluminiscence substrate with high luminescence intensity, long wavelength and good stability and preparation method and application of chemiluminiscence substrate
  • Chemiluminiscence substrate with high luminescence intensity, long wavelength and good stability and preparation method and application of chemiluminiscence substrate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Taking quinoline nitrile chemiluminescent substrate as an example, the specific synthetic route is as follows:

[0038]

[0039] 1. Synthesis of 4-bromo-3-(dimethoxymethyl)phenol

[0040]

[0041] Add 4-bromo-3-hydroxyl-phenol (1g, 4.55mmol) and 20mL methanol into a 50mL dry single-necked bottle, stir to dissolve; then add p-toluenesulfonic acid (171.3mg, 0.91mmol), and reflux for 6h; After completion, the reaction solution was poured into 200ml of dilute sodium carbonate solution (2g), and extracted with ethyl acetate (200mL×2), the extracts were combined, dried over anhydrous sodium sulfate, spin-dried, purified by column chromatography, pale pink liquid 0.7 g, yield 57%.

[0042] 1 H NMR (400MHz, CDCl 3 -d 1 , ppm): δ=7.40-7.38(d, J=8.4Hz, 1H, Ph-H), δ=7.12-7.11(d, J=3.2Hz, 1H, Ph-H), δ=6.73-6.70( d-d, J 1 =8.8Hz,J 2 =3.2Hz,1H,Ph-H),δ=5.84(s,1H,Ph-OH),δ=5.50(s,1H,-CH-O-),δ=3.41(s,6H,-O- CH 3 ). 13 C NMR (100MHz, CDCl 3 -d 1,ppm): 155.51, 133.74, 117...

Embodiment 2

[0069] Other chemiluminescent hydroxyl substrates, the specific synthetic route is as follows:

[0070] 1. Synthesis of Self-luminescent Indole Substrates

[0071]

[0072] Add sulfonate indole salt (322mg, 1.08mmol), quinoline nitrile (300mg, 0.90mmol) and 50ml acetonitrile into a 100mL round bottom flask, stir and mix well; then add sodium acetate (74mg, 0.90mmol); heat to reflux 10h, point the plate to monitor the reaction progress. After the reaction was completed, a red crude product was obtained by rotary evaporation, which was purified by a flash column to obtain 270 mg of a light red solid product with a yield of 53%.

[0073] 1 H NMR (400MHz, CDCl 3 -d 1 , ppm): δ=7.82-7.79(m, 1H, Ph-H), δ=7.59-7.57(d, J=8Hz, 1H, Ph-H), δ=7.53-7.49(m, 3H, Ph-H) H), δ=7.48-7.44(d, J=16Hz, 1H, Alkene-H), δ=7.12(s, 1H, Ph-H), δ=7.02-6.98(d, J=16Hz, 1H, Alkene -H),δ=6.92-6.89(d-d,J 1 =8.4Hz,J 2 =2.8Hz,1H, Ph-H),δ=6.81-6.80(d,J=2.8Hz,1H,Ph-H),δ=4.42-4.36(q,J=6.8Hz,2H,-N-CH 2 -C...

Embodiment 3

[0082] Absorption, Fluorescence and Chemiluminescence Spectra of F-QM-OH in Aggregated State

[0083] Get the F-QM-OH prepared in Example 1 and dissolve it in analytically pure dimethyl sulfoxide to make 1.0 × 10 -2 stock solution of M. Then prepare water (H 2 O) 99% DMSO / H 2 O mixed solvent 2mL. Take 20 μL of the above stock solution and add it to the prepared DMSO / HO 2 O mixed solvent, mixed evenly and transferred to an optical quartz cuvette (10 × 10mm) to test its fluorescence spectrum. Such as figure 1 As shown, with 480nm as the excitation wavelength, the maximum emission peak of the F-QM-OH substrate is located at about 600nm in the near-infrared region, and the Stokes shift is 120nm; the chemiluminescence spectrum of F-QM-OH is basically consistent with the fluorescence spectrum .

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Abstract

The invention provides a chemiluminiscence substrate with high luminescence intensity, a long wavelength and good stability and a preparation method and application of the chemiluminiscence substrate.The chemiluminiscence substrate is of a structure of a formula I shown in the description. In addition, the invention provides an autofluorescence wavelength and intensity of a chemiluminiscence probe in a physiological environment and application of the chemiluminiscence probe in living imaging. Testing results shown that the chemiluminiscence probe provided by the invention has autofluorescenceof a long wavelength (600nm), is capable of effectively penetrating skin tissue, and has high autofluorescence intensity (greater than 10<7>p/s/cm<2>/sr), excellent thermal stability (without 1,2-dioxy-heterocyclobutane structure) and diverse detection groups (applicable to different detection models).

Description

technical field [0001] The invention belongs to the field of fine chemicals, and specifically relates to a synthesis method and biological application of a novel chemiluminescent probe based on an electron-rich methoxy-alkenyl group. Background technique [0002] Chemiluminescence is a kind of light radiation phenomenon accompanied by the chemical reaction of substances. Since no exogenous excitation light is required, chemiluminescence detection can effectively overcome the intractable problems of photobleaching, light scattering and autofluorescence in traditional fluorescence detection methods (Talanta 2000, 51, 415-439). In addition, chemiluminescent detection also has significant advantages such as low detection limit, high sensitivity, and wide range of analyte detection concentrations, so chemiluminescent probes have attracted the attention of chemists and biologists. In 1987, Paul Schaap reported for the first time a chemiluminescence substrate with a 1,2-dioxane ri...

Claims

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Application Information

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IPC IPC(8): C07D209/12C07D215/12C07D409/14C07F5/02C09K11/06G01N21/76
CPCC07D209/12C07D215/12C07D409/14C07F5/022C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1092C09K2211/1096G01N21/76
Inventor 郭志前朱为宏张玉涛燕宸旭徐清爽李娟张辽王婷常茂菊
Owner EAST CHINA UNIV OF SCI & TECH
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