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Preparation method and application of hydrogen peroxide ratio type fluorescent molecular probe based on DCPO mother nucleus

A fluorescent molecular probe, hydrogen peroxide technology, applied in the field of analytical chemistry, can solve the problems of not well revealing the role of hydrogen peroxide, poor biocompatibility, short emission wavelength, etc., and achieves strong practical application value and specificity. High, chemically stable high effect

Active Publication Date: 2021-06-22
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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  • Preparation method and application of hydrogen peroxide ratio type fluorescent molecular probe based on DCPO mother nucleus
  • Preparation method and application of hydrogen peroxide ratio type fluorescent molecular probe based on DCPO mother nucleus
  • Preparation method and application of hydrogen peroxide ratio type fluorescent molecular probe based on DCPO mother nucleus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis of compound 1

[0035] At room temperature, DCPO (936.9 mg, 3 mmol) and hexamethylimidinium (1400 mg, 10 mmol) were added to a 25 mL round bottom flask in a 25 mL round bottom flask, and then 25 mL of trifluoro Acetic acid, heated to 90 o C is heated to reflux. After the reaction is over, take off the reaction, let it cool and pour it into 500 mL of ice water, adjust the pH to about 6 with 1 mol / L NaOH solution, and precipitate a large amount of precipitate, suction filter, collect and wash the filter cake, After vacuum drying, 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 dissolved in 20 mL of ...

Embodiment 2

[0041] The experiment of the relationship between the fluorescence intensity of the fluorescent probe and the concentration change 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 acetonitrile solution, and prepare a 1 mM probe mother solution. Take 20 μL from the mother liquor and add it to a 5mL centrifuge tube, add hydrogen peroxide standard solutions of different concentrations, dilute with PBS buffer solution (10 mM, pH=7.4), adjust the concentration of the probe compound in the solution to 10 μM, and the concentrations of hydrogen peroxide were 1 μM, 3 μM, 5 μM, 10 μM, 15 μM, 20 μM, 30 μM, 40 μM, and after incubation at room temperature for 20 min, the different concentrations were tested in 10 mm cuvettes. Fluorescence spectra of the system. Fluorescence spectra such as figure 1 shown. The results showed that w...

Embodiment 3

[0044] Selectivity of Fluorescent Probes to Hydrogen Peroxide

[0045] The fluorescent probe prepared in Example 1 was mixed with six reactive oxygen species (O 2 -, NO, ClO-, tert-butanol peroxide, HO·, NO 3 -), two thiol amino acids (L-cysteine, L-glutathione), one metal ion (Fe 3+ ) 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 was carried out in PBS buffer solution (10mM, pH=7.4). In the entire detection system, the concentration of the probe molecule was 10 μM, the concentration of other compounds to be detected was 30 μM hydrogen peroxide, and the concentrations of the other compounds were After incubating at room temperature for 20 min at 100 μM, detect the fluorescence spectra of different systems, record the fluorescence intensities at 695 nm and 510 nm and calculate the I 695 nm / I 510 nm value. The results are attached image 3 As shown, it was found that only...

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Abstract

The invention discloses a preparation method and application of a hydrogen peroxide ratio type fluorescent molecular probe based on a DCPO mother nucleus. The chemical structural formula of the hydrogen peroxide ratio type fluorescent molecular probe is shown in the specification. The fluorescent molecular probe provided by the invention can be used for ratio type detection of hydrogen peroxide in a pure water system and a biological system, the interference of other detection conditions can be greatly reduced, and the detection precision is improved; meanwhile, the probe further has the advantages of being good in water solubility, high in sensitivity and high in specificity, interference of other objects to be detected can be avoided, finally, the probe has high red light emission, interference of biological autofluorescence can be effectively avoided, cell membrane permeability is good, cytotoxicity is small, and the probe has high practical application value in the fields of environment, life science and the like.

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 (reactive oxygen species, ROS) is a general term for a class of molecules or ions that are chemically active and have high oxidation activity, and play an important role in regulating physiological functions and pathological processes. Hydrogen peroxide (H2O2) is an important part of the reactive oxygen species family, and has attracted attention and research because of 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 living organisms. Thus, depending on the degree, timing and location of its production, it has a variety of physiological and pathological roles in living cells...

Claims

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Application Information

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Patent Type & Authority Applications(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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