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Fluorescent probe, and preparation method and application thereof in reversible detection of hydrosulfite/hydrogen peroxide in vivo

A bisulfite and fluorescent probe technology, applied in the field of fluorescent probes, can solve the problems of not being able to monitor the redox balance at the same time, fluorescent probes have not been reported, and achieve easy scale production, simple process, and easy control of conditions Effect

Active Publication Date: 2020-02-18
UNIV OF SCI & TECH LIAONING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Currently reported fluorescent molecular probes, a probe can usually only recognize a single target of bisulfite or hydrogen peroxide, but cannot simultaneously monitor the redox balance regulated by bisulfite and hydrogen peroxide in organisms
Although a small number of probes have been applied to the reversible detection of bisulfite and hydrogen peroxide at the level of living cells, fluorescent probes for the reversible detection of bisulfite and hydrogen peroxide in vivo have not been reported.

Method used

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  • Fluorescent probe, and preparation method and application thereof in reversible detection of hydrosulfite/hydrogen peroxide in vivo
  • Fluorescent probe, and preparation method and application thereof in reversible detection of hydrosulfite/hydrogen peroxide in vivo
  • Fluorescent probe, and preparation method and application thereof in reversible detection of hydrosulfite/hydrogen peroxide in vivo

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preparation example Construction

[0039] The present invention provides a method for preparing a fluorescent probe described in the above scheme, comprising the following steps:

[0040] The raw material I and the raw material II are subjected to a nucleophilic addition-elimination reaction under the catalysis of piperidine to obtain a fluorescent probe having the structure shown in formula 1;

[0041] The structures of the raw material I and the raw material II are shown in formula 2 and formula 3 respectively:

[0042]

[0043] In formula 3, R is -CH 3 、-CH 2 CH 3 、-CH 2 CH 2 CH 3 、-CH 2 CH 2 CH 2 OH or

[0044] In the present invention, the molar ratio of the raw material I and the raw material II is preferably 1:1; the present invention has no special requirements on the source of the raw material I and the raw material II, and adopts commercially available products well known in the art or adopts The well-known preparation method can be prepared by oneself. In the present invention, the so...

Embodiment 1

[0054] (1) Synthesis of fluorescent probes

[0055] Each 1mol of the two raw materials shown in formula 2 and formula 3 (in formula 3, R=-CH 2 CH 3 ) was dissolved in 20 mL of dry methanol, and then 2 drops of piperidine were added to catalyze the reaction. The mixture was heated under reflux for 10 hours to stop the reaction, and the organic solvent was distilled off under reduced pressure. The crude product was purified by chromatographic silica gel column (developing solvent: dichloromethane / ethyl acetate v / v, 20:1) to obtain the blue-purple target product with a yield of 31%. The characterization data of the resulting product are as follows:

[0056] 1 H NMR (DMSO-d 6 ,600MHz),δ(ppm)8.49(s,1H),8.38(s,1H),8.25(s,1H),8.23(d,J=7.38Hz,1H),7.80(t,J=9.96Hz, 2H), 7.72(d, J=8.16Hz, 1H), 7.65(d, J=8.16Hz, 1H), 7.52(t, J=6.9Hz, 1H), 7.36(d, J=8.52Hz, 1H) ,7.28(t,J=6.84Hz,1H),7.21(s,1H),4.46(d,J=6.54Hz,2H),3.69(m,4H),3.09(m,2H),2.85(m, 2H), 1.90(m, 2H), 1.28(t, J=6.54Hz, 12H)...

Embodiment 2

[0081] Each 1mol of the two raw materials shown in formula 2 and formula 3 (in formula 3, R=-CH 3 ) was dissolved in 20 mL of dry methanol, and then 2 drops of piperidine were added to catalyze the reaction. The mixture was heated under reflux for 6 hours, the reaction was stopped, and the organic solvent was distilled off under reduced pressure. The crude product was purified by chromatographic silica gel column (developing solvent: dichloromethane / ethyl acetate v / v, 20:1) to obtain the blue-purple target product, which conforms to formula 1 (R=-CH 3 ), the fluorescent probe was successfully prepared.

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Abstract

The invention provides a fluorescent probe, and a preparation method and an application thereof in reversible detection of hydrosulfite / hydrogen peroxide in vivo, and relates to the technical field offluorescent probes. The fluorescent probe provided by the invention has a structure represented by a formula 1, wherein in the formula 1, R is -CH3, -CH2CH3, -CH2CH2CH3, -CH2CH2CH2OH or a group described in the specification. The fluorescent probe provided by the invention has the advantages of near-infrared fluorescence emission, high specificity, high sensitivity, suitability for physiologicalpH and low cytotoxicity; redox balance regulated and controlled by hydrosulfite and hydrogen peroxide can be reversibly detected, particularly, redox balance regulated and controlled by hydrosulfite and hydrogen peroxide in a living body can be reversibly detected, and the blank of application of a conventional fluorescent probe is filled up. The invention provides the preparation method of the fluorescent probe, and the preparation method provided by the invention is simple in process, easy in condition control and prone to realization of large-scale production.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, in particular to a fluorescent probe, a preparation method thereof and an application in reversible detection of bisulfite / hydrogen peroxide in vivo. Background technique [0002] Reactive oxygen species (ROS) and reactive sulfur species (RSS) play important roles in physiological and pathological processes in the human body. Bisulfite (HSO 3 – ) is an important active sulfur species and also a food additive. It is often used in food or wine to prevent oxidation, browning, bacterial fermentation and other processes. It is also widely used in the pharmaceutical and paper industries. In addition, bisulfite, as the main form of the gas signal molecule sulfur dioxide in the body, has important physiological functions such as anti-oxidation and regulation of cardiovascular structure and function. Excessive intake of bisulfite can easily cause asthma and allergic reactions; abnormal level...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06C09K11/06G01N21/64
CPCC07D405/06C09K11/06C09K2211/1029C09K2211/1088G01N21/6428
Inventor 贾宏敏张志强李绵宋秋颖胡文博孟庆涛王月朱珮珣周博
Owner UNIV OF SCI & TECH LIAONING
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