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A kind of preparation method and application of hydrogen peroxide ratio fluorescent molecular probe based on dcpo core

A fluorescent molecular probe, hydrogen peroxide technology, applied in the field of analytical chemistry, can solve the problems of not being able to reveal the effect of hydrogen peroxide well, poor biocompatibility, short emission wavelength, etc., and achieve strong practical application value and specificity High, stable chemical properties and high effect

Active Publication Date: 2022-07-08
HUNAN TARGETING DETECTION TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the short emission wavelength of this probe leads to its poor biocompatibility, and it is greatly disturbed by background fluorescence in vivo, which cannot well reveal the role of hydrogen peroxide in cellular processes and biological growth and development.

Method used

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  • A kind of preparation method and application of hydrogen peroxide ratio fluorescent molecular probe based on dcpo core
  • A kind of preparation method and application of hydrogen peroxide ratio fluorescent molecular probe based on dcpo core
  • A kind of preparation method and application of hydrogen peroxide ratio fluorescent molecular probe based on dcpo core

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis of Compound 1

[0035] At room temperature, in a 25 mL round bottom flask, DCPO (936.9 mg, 3 mmol) and hexamethylimidine (1400 mg, 10 mmol) were added to a 25 mL round bottom flask, and then 25 mL of trifluoro trifluoride was added to the reaction system. Acetic acid, warm to 90 o After the reaction is completed, remove the reaction, pour it into 500 mL of ice water after cooling, adjust the pH to about 6 with 1 mol / L NaOH solution, and precipitate a large amount of precipitates, filter, collect and wash the filter cake, After drying in vacuo, it was purified by column chromatography to obtain 810.6 mg of the product with a yield of 79.4%. 1 H NMR (400 MHz, DMSO-d 6 , ppm): δ 10.36 (s, 1H), 7.89-7.91(m, 1H), 7.79 (d, 1H, J =7.6 Hz), 7.72(d, 1H, J =16.0 Hz), 7.89-7.62 (m, 3H), 7.28 (d, 1H, J =16.0 Hz,), 6.98 (s, 1H), 6.85 (d, 1H, J =8.8 Hz), 5.56(s, 1H), 5.35(s, 1H).

[0036] Synthesis of Compound 2

[0037] Compound 1 (680.6 mg, 2 mmol) was dissolv...

Embodiment 2

[0041] Experiment on the relationship between the fluorescence intensity of fluorescent probe and the concentration of hydrogen peroxide

[0042] Accurately weigh 661.5 mg of the target fluorescent molecular probe with a purity of more than 99% prepared in Example 1, transfer it to a 50 mL volumetric flask, dissolve it in an acetonitrile solution, and prepare a 1 mM probe stock solution. Take 20 μL from the mother solution and add it to a 5 mL centrifuge tube, add hydrogen peroxide standard solutions of different concentrations, dilute with PBS buffer solution (10 mM, pH=7.4), and adjust to the concentration of the probe compound in the solution to be 10 μM, and the concentrations of hydrogen peroxide were 1 μM, 3 μM, 5 μM, 10 μM, 15 μM, 20 μM, 30 μM, and 40 μM, respectively. After 20 min incubation at room temperature, the different concentrations were tested in 10 mm cuvettes. Fluorescence spectrum of the system. Fluorescence spectra such as figure 1 shown. The results sh...

Embodiment 3

[0044] Selectivity of fluorescent probes for hydrogen peroxide

[0045] The fluorescent probe prepared in Example 1 was mixed with six reactive oxygen species (O 2 -, NO, ClO-, tert-butanol peroxy, HO , NO 3 -), two thiol amino acids (L-cysteine, L-glutathione), a metal ion (Fe 3+ ) to respond respectively to test their response. In order to ensure the comparability of the experimental results, the whole reaction system was set at 25 o C in PBS buffer solution (10mM, pH=7.4), in the whole detection system, the concentration of probe molecules is 10 μM, the concentration of other compounds to be detected is 30 μM hydrogen peroxide, and the concentrations of other compounds are After incubation at room temperature for 20 min at 100 μM, the fluorescence spectra of different systems were detected, the fluorescence intensities at 695 nm and 510 nm were recorded and I was calculated. 695 nm / I 510 nm value of . The results are attached image 3 As shown, it is found that only...

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Abstract

The invention discloses a preparation method and application of a hydrogen peroxide ratio fluorescent molecular probe based on a DCPO core, and its chemical structural formula is as follows: The ratiometric detection of hydrogen oxide can greatly reduce the interference of other detection conditions and improve the detection accuracy. At the same time, the probe also has the advantages of good water solubility, high sensitivity and strong specificity, which can avoid the interference of other analytes. The probe has strong red light emission, can effectively avoid the interference of biological autofluorescence, has good cell membrane permeability and low cytotoxicity, and has strong practical application value in the fields of environment and life sciences.

Description

technical field [0001] The invention relates to a preparation method and application of a hydrogen peroxide ratio fluorescent molecular probe based on a DCPO core, belonging to the technical field of analytical chemistry. Background technique [0002] Reactive oxygen species (ROS) is a general term for a class of molecules or ions with active chemical properties and high oxidative activity, which play an important role in regulating physiological functions and pathological processes. Hydrogen peroxide (hydrogen peroxide) is an important part of the reactive oxygen species family and has received attention and research due to its relatively mild reactivity in biological systems. Studies have shown that hydrogen peroxide is a product of most oxidase processes and participates in regulatory processes in organisms. Therefore, it has a variety of physiological and pathological roles within living cells, depending on the extent, timing and location of its production. At normal p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/025C09K11/06G01N21/643G01N21/6428C09K2211/1007C09K2211/1014C09K2211/1037C09K2211/1088C09K2211/1096
Inventor 曾文彬李石陈小洪
Owner HUNAN TARGETING DETECTION TECH CO LTD
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