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Coumarin derivative DOCOPA as well as preparation method and application thereof

A technology for coumarin derivatives and coumarin, applied in chemical instruments and methods, instruments, analytical materials, etc., can solve problems such as research limiting physiological and pathological effects, fluorescent probe limitations, etc., and achieve excellent sensitivity and selectivity, broad application prospects, and simple detection process.

Inactive Publication Date: 2017-02-22
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Due to the similarity in the structure and properties of Cys and Hcy, the fluorescent probes are greatly limited in the detection and labeling of Cys and Hcy, thus limiting the study of their physiological and pathological roles

Method used

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  • Coumarin derivative DOCOPA as well as preparation method and application thereof
  • Coumarin derivative DOCOPA as well as preparation method and application thereof
  • Coumarin derivative DOCOPA as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation of DOCOPA:

[0033] 1) Synthesis of compound I:

[0034]

[0035] Dissolve 3-acetyl-7-N,N-diethylaminocoumarin (6mmol, 1.55g) and p-hydroxybenzaldehyde (6mmol, 0.732g) in 30mL of acetonitrile, add 3-5 drops of piperidine, Reflux for 11 hours until the reaction is complete; the system is cooled to room temperature, filtered with suction, washed with acetonitrile, and the filter cake is dried to obtain compound I.

[0036] 2) Synthesis of compound DOCOPA:

[0037]

[0038] Dissolve compound I (1mmol, 0.36g) and triethylamine (1mmol) in dichloromethane, gradually add acryloyl chloride (1.4mmol) dropwise in an ice bath, stir at room temperature for 20 hours after the dropwise addition, until the reaction is complete; After being evaporated to dryness under pressure, the target compound DOCOPA was obtained by column chromatography (ethyl acetate:petroleum ether=1:3 by volume).

[0039] 1 H NMR (600MHz, DMSO-d 6 ):δ8.62(s,1H),7.96(d,J=15.8Hz,1H),7.80(d,...

Embodiment 2

[0041] Prepare HEPES buffer solution with pH=7.8 and concentration of 10mM, prepare 2mM DOCOPA in DMSO solution, prepare 20mM Cys aqueous solution; take 2mL of HEPES / DMSO (v / v, 1:1, pH 7.8) solution, 30μL DOCOPA in DMSO The solution was added to a fluorescence cuvette, and 30 μL Cys aqueous solution was added, and detected on a fluorescence spectrophotometer (447nm excitation) over time. Within 0-12min, the fluorescence intensity at 499nm gradually increased; after 12min, the fluorescence intensity at 499nm gradually decreased, and the fluorescence intensity at 554nm gradually increased. See the fluorescence emission diagram figure 2 .

Embodiment 3

[0043] Prepare HEPES buffer solution with pH=7.8 and concentration of 10mM, prepare 2mM DOCOPA in DMSO solution, prepare 20mM Hcy aqueous solution; take 2mL of HEPES / DMSO (v / v, 1:1, pH 7.8) solution, 30μL DOCOPA in DMSO The solution was added to a fluorescence cuvette, and 30 μL of Hcy aqueous solution was added, and detected on a fluorescence spectrophotometer (excitation at 447 nm) over time. The fluorescence intensity at 499nm increases gradually, and the fluorescence emission diagram is shown in image 3 .

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Abstract

The invention provides a coumarin derivative DOCOPA as well as a preparation method and an application thereof. The English name of DOCOPA is (E)-4-(3-(7-(diethylamino)-2-oxo-2Hchromen-3-yl)-3-oxoprop-1-en-1-yl) phenylacrylate). The preparation method comprises the steps that 3-acetyl-7-diethylaminocoumarin and p-hydroxybenzaldehyde are dissolved in acetonitrile firstly, a catalytic amount of piperidine is added, and reflux is performed until a reaction is performed sufficiently; an intermediate compound is further obtained; the intermediate compound and triethylamine are dissolved in dichloromethane, acryloyl chloride is added dropwise gradually to an ice bath, room-temperature stirring is performed until a reaction is performed sufficiently, a product is subjected to column chromatography separation after reduced-pressure evaporation, and the DOCOPA is obtained. The DOCOPA is applied to distinguishing and detection of cysteine and homocysteine in a pH7.8 system and imaging of the cysteine and the homocysteine in cells. The DOCOPA shows high sensitivity and selectivity for the cysteine and the homocysteine.

Description

technical field [0001] The invention relates to a detection and analysis technology for thiols, in particular to a coumarin derivative DOCOPA and a preparation method thereof, as well as the application of DOCOPA in the detection of cysteine ​​and homocysteine. Background technique [0002] Cysteine ​​(Cys) is the only amino acid with a reducing sulfhydryl group (-SH) among the 20 natural amino acids. As the precursor of glutathione, it plays a series of important roles in redox regulation, biocatalysis, etc. character of. At the same time, abnormal Cys levels in the human body are closely related to diseases such as slow growth, liver damage, skin damage, and muscle damage in children. It is of great scientific significance to detect Cys in organisms. [0003] Homocysteine ​​(Hcy) is an important intermediate product in the metabolic process of methionine and cysteine. It is metabolized in the body mainly through two pathways: remethylation and transsulfuration. The abno...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06C09K2211/1007C09K2211/1088G01N21/643G01N21/6486
Inventor 岳永康霍方俊阴彩霞
Owner SHANXI UNIV
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