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Organic compound for detecting histamine and application of organic compound

A technology of organic compounds and compounds, applied in the field of fluorescent probes, to achieve the effect of reducing interference and improving detection sensitivity

Active Publication Date: 2018-11-02
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cannot be used to accurately detect the presence of histamine in vivo

Method used

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  • Organic compound for detecting histamine and application of organic compound
  • Organic compound for detecting histamine and application of organic compound
  • Organic compound for detecting histamine and application of organic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of the compound shown in formula I: under ice-bath conditions, 3,5-bistrifluoromethylthiophenol (264mg, 1.07mmol) was dissolved in 80ml of anhydrous DMF and placed in a 250ml round-bottomed flask. 20ml of anhydrous DMF dissolved NaH (430mg, 1.07mmol) and placed in a constant pressure dropping funnel and dripped into the reaction bottle, stirred for 20min, and then commercialized cyanine dye Cy 7 -Cl (640mg, 1mmol) was added to the reaction system, such as figure 2 . Reacted for 90 minutes, extracted three times with dichloromethane and NaI aqueous solution, the organic layer was rotary evaporated to remove the solvent, and the crude product was purified by column chromatography to obtain 704 mg of the green product of the compound represented by formula I, with a yield of 83%.

[0033] 1 H NMR (500MHz, CDCl 3 )δ(ppm): 1 H NMR (500MHz, CDCl 3 -D 1 )δ8.59-8.56(d,2H),7.67(s,2H),7.59(s,1H),7.42–7.36(m,4H),7.27–7.24(m,4H),6.31-6.28(d, 2H), 4.30-4.28(q, 4H),...

Embodiment 2

[0035] Spectral properties of compound formula Ⅰ

[0036] The prepared compound of formula I is used as a probe in water system, simulated physiological environment and cells to detect histamine. The following experiments are all carried out under the condition of pH=7.4 (HEPES buffer solution, concentration is 10mM), the concentration of probe 1 mM was used.

[0037] The compound of formula I prepared above is used as the response of probe to histamine:

[0038] Add 100 μL of the compound of Formula I (1mM) to a 10mL colorimetric tube, dilute to 10.0mL with 10mM HEPES buffer solution (pH 7.4), shake the solution for 10min and take 1mL in a fluorescent cuvette to measure the fluorescence spectrum at 750nm-860nm . Add 1mL of histamine (100μM) to the above colorimetric tube to make up to 10mL, shake the solution to balance for 10min, absorb 1mL of the working solution in the colorimetric tube into a fluorescent dish to measure the fluorescence spectrum, and measure the fluores...

Embodiment 3

[0040] The selectivity of compound formula I to histamine

[0041] Take nine 10mL colorimetric tubes, and add 100 μL of the compound of formula I to each colorimetric tube, then add 8 mL of HEPES buffer solution with a pH of 7.4, and then add 1 mL of the substance to be tested (100 μM): (1) histamine, (2) Histidine, (3) Tryptophan, (4) Ammonia, (5) Alanine, (6) Glutathione, (7) Cysteine, (8) Hydrogen peroxide, ( 9) Ascorbic acid. Finally, the volume was adjusted to 10ml with HEPES buffer. Shake the solution at room temperature and equilibrate in the dark for 10 minutes, pour 1 mL of the working solution in each colorimetric tube into a fluorescent dish to measure the fluorescence spectrum in the range of 680nm-800nm ​​(see Figure 5 ).

[0042] Depend on Figure 5 From the experimental results, it can be concluded that the compound of formula Ⅰ, as a probe, has a selective response to histamine and is not interfered by other biological amino acids, active sulfur, and activ...

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Abstract

The invention relates to a fluorescence probe, in particular to an organic compound for detecting histamine on the basis of cyanine fluorophores and an application of the organic compound. The compound is the organic compound based on cyanine, and the structural formula is represented as formula I in the description. According to the fluorescence probe, fluorescence emission wavelength and strength both change in the presence of histamine, and the fluorescence probe can be applied to detection of bioactive histamine. Background interference of an external environment is greatly reduced on thebasis of near-infrared spectral characteristics of the compound, and detection sensitivity is improved by ratio fluorescence detection. The compound serving as the fluorescence probe can be applied tohistamine detection of cells and complex biological samples and has great biomedical significance for studying dynamics mechanism of histamine production and accumulation and cell signaling transduction and discovering fluctuation conditions and actions of histamine content in diseases.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to an organic compound for detecting histamine based on a cyanine fluorophore and an application thereof. Background technique [0002] As a transmitter, histamine widely exists in various tissues, organs and blood. Histamine in the body is an autologous active substance formed by decarboxylation of histidine by histidine decarboxylase. It is mainly produced by mast cells and basophils. When the body is stimulated or allergic reaction occurs, it is released by degranulation and combines with various types of histamine receptors to produce allergic and inflammatory reactions. Histamine receptors are mainly distributed in various regions of the brain and have a lower expression density in other peripheral organs and systems. Changes in the concentration of histamine in the body are closely related to various inflammatory and infectious diseases. The mechanism of action of histamine is complex a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D209/10G01N21/64
CPCA61K49/0021C07D209/10C09K11/06C09K2211/1007C09K2211/1029G01N21/6428G01N21/643
Inventor 陈令新张霞于法标高敏黄严
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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