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A near-infrared fluorescent probe for quantitative detection of endogenous hydrogen peroxide and its preparation method and application

A quantitative detection and hydrogen peroxide technology, applied in the field of chemical analysis and detection, can solve the problems of not well revealing the role of hydrogen peroxide, low probe selectivity, large interference, etc., and achieves high selectivity and high purity. , the effect of reducing interference

Active Publication Date: 2020-10-16
江苏中煦科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Existing art studies of hydrogen peroxide signaling have focused on identifying mechanisms that regulate hydrogen peroxide production, and as large-scale studies identify an increasing number of proteins that are sensitive to thiol oxidation, it is important to determine which proteins under physiological conditions There are few studies on the quantitative detection of endogenous hydrogen peroxide in cells, and the current probes for detecting hydrogen peroxide are not high in selectivity, and are greatly interfered by background fluorescence in vivo, so they cannot be well Uncovering the role of hydrogen peroxide in cellular processes as well as in biological growth and development

Method used

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  • A near-infrared fluorescent probe for quantitative detection of endogenous hydrogen peroxide and its preparation method and application
  • A near-infrared fluorescent probe for quantitative detection of endogenous hydrogen peroxide and its preparation method and application
  • A near-infrared fluorescent probe for quantitative detection of endogenous hydrogen peroxide and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Preparation of organic compound of formula I based on cyanine:

[0044] (1) Ethyl group on phenacindole: Dissolve benzoindole (24g) and ethyl iodide (18g) in 50mL of anhydrous acetonitrile at 80°C and reflux for 12h to obtain the purple product a;

[0045] (a);

[0046] (2) Take 40mL of anhydrous DMF and 40mL of anhydrous dichloromethane and mix them evenly to obtain a mixed solvent. Stir the mixed solvent at -10°C for 20 minutes, and add 37mL of POCl dropwise during the stirring process 3 Mix the solution with 35mL of anhydrous dichloromethane, then add 10g of cyclohexanone, stop cooling for 2-3h, raise the temperature to 45°C and heat for 3h, pour the yellow liquid obtained from the reaction into ice while stirring, overnight, and suction filter Vacuum drying gives yellow solid b;

[0047] (b);

[0048](3) Weigh 1 g of b and 6 g of a, dissolve b and a in a mixed solution of 210 mL of toluene and 90 mL of n-butanol, heat to reflux at 80°C, and purify by silica g...

Embodiment 2

[0055] The prepared compound of formula I was used as a probe to detect hydrogen peroxide in cells, tissues and organs to simulate physiological conditions. The following experiments were carried out at pH = 7.4 (HEPES buffer solution, concentration 40 mM) , the concentration of the probe was 10 μM.

[0056] The ultraviolet response of the compound of formula I prepared above to MAO:

[0057] pH was controlled with HEPES buffer solution. Add 10 μM compound formula 1 to a 10 mL colorimetric tube, then add 40 mM HEPES, then add hydrogen peroxide, dilute with ultrapure water and set the volume to 0-200 μM, shake the solution, and equilibrate for 10 minutes, then add the above working solution The UV absorption spectrum was measured in a cuvette. The changes of ultraviolet absorption spectrum before and after detecting hydrogen peroxide are as follows: image 3 with 4 As shown, the changes in ultraviolet absorption of fluorescent probes before and after hydrogen peroxide detec...

Embodiment 3

[0059] Embodiment 3 Formula I compound is to the selectivity of hydrogen peroxide

[0060] pH was controlled with HEPES buffer solution. Take multiple 10 ml colorimetric tubes, and add 10 μM compound formula 1 to each 10 ml colorimetric tube, then add 40 mM HEPES buffer solution with pH 7.4, and then add such as Image 6 As shown, the analytes are as follows: H 2 0 2 , t-BuO, Glu, TBHP, O2 - ,NO, . OH,OCl - , Cys, His, GSH. Finally, dilute to 10 ml with ultrapure water. Shake the solution evenly, and after equilibrating at 25°C for 10 min, pour the working solution in each colorimetric tube into a fluorescent dish to measure the fluorescence spectrum. Compound of formula one to hydrogen peroxide - selectivity such as Image 6 shown. And by Image 6 It can be seen that the compound of formula one has good selectivity to hydrogen peroxide, and specifically recognizes hydrogen peroxide. Compared with hydrogen peroxide probes in the prior art, the probe prepared by the...

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Abstract

The invention belongs to the technical field of chemical analysis and detection and in particular relates to a near-infrared fluorescence probe for rated quantitative determination on endogenous hydrogen peroxide and a preparation method and application of the near-infrared fluorescent probe. The near-infrared fluorescence probe has a structural formula as shown in the specification. The near-infrared fluorescence probe is applied to rate detection on hydrogen peroxide; in the presence of hydrogen peroxide, a corresponding fluorescence wavelength is conspicuous displaced, then detection and quantification on exogenous and endogenous hydrogen peroxide can be implemented, interference of external detection conditions can be greatly reduced, and the detection precision can be improved. By adopting the compound of the fluorescence probe for rated quantitative determination on hydrogen peroxide, ultraviolet absorption can be also conspicuous changed in the presence of hydrogen peroxide, anddetection can be carried out by using an ultraviolet spectrophotometer and naked eyes simultaneously. As the fluorescence probe, the compound can be applied to detection on levels of hydrogen peroxide inside and outside cells, and the fluorescence probe has very great instruction significances for studying hydrogen peroxide in the mitosis process, and particularly for studying functions of the hydrogen peroxide as a messenger molecule.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a near-infrared fluorescent probe for ratiometric detection of endogenous hydrogen peroxide, a preparation method and an application thereof. Background technique [0002] Hydrogen peroxide is a small molecule in living organisms, and increased levels of hydrogen peroxide in cells can lead to oxidative stress and cause cellular damage. Indeed, this damage has been linked to the initiation and progression of many diseases, including neurodegenerative diseases, diabetes, atherosclerosis and cancer. However, studies in higher eukaryotes have revealed that hydrogen peroxide is also used as a signaling molecule regulating many different cellular processes. [0003] Existing art studies of hydrogen peroxide signaling have focused on identifying mechanisms that regulate hydrogen peroxide production, and as large-scale studies identify an increasing n...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D209/60G01N21/64A61K49/00
CPCA61K49/0032C07D209/60C09K11/06C09K2211/1007C09K2211/1029G01N21/6486
Inventor 陈光郭海龙于法标高敏尤进茂
Owner 江苏中煦科技有限公司
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