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The near-infrared fluorescent probe substrate of comt and its application

A fluorescent probe and probe substrate technology, applied in the field of biomedicine, can solve problems affecting the accuracy of enzyme activity, weak anti-interference ability, substrate oxidation degradation, etc., achieve good fluorescence emission characteristics, strong anti-interference ability, The effect of improving accuracy

Active Publication Date: 2022-03-11
WUXI ERYUN TECH CO LTD
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  • Claims
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AI Technical Summary

Problems solved by technology

[0004] However, the currently commonly used COMT probe substrates have the following defects: 1. Low detection throughput: the methylated products that are catalyzed by COMT into two isomers need to be separated and enriched by means of HPLC, and the analysis process cumbersome and time-consuming; 2. Weak anti-interference ability: commonly used substrates are mostly endogenous compounds, which are easily interfered by biological matrices; 3. Poor stability: substrates are prone to oxidative degradation in the reaction system, which affects the accuracy of enzyme activity detection

Method used

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  • The near-infrared fluorescent probe substrate of comt and its application
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  • The near-infrared fluorescent probe substrate of comt and its application

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Embodiment 1

[0036] 1. Synthesis of TCFC:

[0037] Mix 3-formyl-7,8-dihydroxycoumarin (0.41g, 2mmol) with 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-alkylene) Malononitrile (TCF) (0.45g, 2.3mmol) was dissolved in methanol (40ml), piperidine (100μl) was added, the reaction leaf was heated to reflux for 2h, filtered after cooling, the filter cake was recrystallized from methanol, and the crude product was subjected to column chromatography ( dichloromethane / methanol) to obtain the product TCFC, 110 mg of red solid, yield 15%. HRMS(TOF-ESI):m / z C 21 h 13 N 3 o5 :387.0855, mass spectrum shows m / z386.0783[M-H] - .

[0038] 2. Characterization of the optical properties of the probe substrate TCFC and its methylated product TCFMC:

[0039] (1) The probe substrate TCFC and its methylated product TCFMC were dissolved in pH 7.4 Tris-HCl buffer (50 mM) and 1% formic acid-acetonitrile (v / v 1:1) mixture.

[0040] (2) Take 200 μL in a transparent 96-well plate, and scan its absorption spectrum from 20...

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Abstract

The invention discloses a COMT near-infrared fluorescent probe substrate and its application. The probe substrate uses 7,8-dihydroxycoumarin as the mother nucleus, and introduces a conjugated double bond at its C3 position as a linking group , connecting the electron-withdrawing group EWG with hydrophilic / hydrophobic properties, wherein the EWG group is DMIC, TCFC, NIFC or BTC. Compared with the prior art, the present invention has the following advantages: (1) High specificity and sensitivity: the probe substrate can be specifically metabolized by COMT, and its product has good fluorescence emission characteristics. (2) Elcometer-throughput detection: It can be measured on various fluorescent microplate readers and clinical biochemical instruments commonly used in laboratories, and can be detected in batches using 96 or 386 microwell plates. (3) Strong anti-interference ability: the methylated product of the probe substrate can emit fluorescence in the near-infrared region, which has a better ability to resist the autofluorescence of biological substrates, and improves the quantitative accuracy of the enzyme activity method.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and relates to a functional substrate and application thereof, in particular to a near-infrared fluorescent probe substrate of COMT and application thereof. Background technique [0002] Catechol-O-methyltransferase (Catechol-O-methyltransferase, COMT, EC 2.1.1.6) is an important phase II-binding metabolic enzyme in the human body, which can convert S-adenosylmethionine (S- adenosyl-L-methionine, SAM) to the catechol group of the substrate. Human COMT mainly exists in two forms, soluble COMT (S-COMT) and membrane-bound COMT (MB-COMT). S-COMT is the predominant form in peripheral tissues including liver and blood, and plays an important role in the detoxification and metabolism of exogenous catechol compounds and catechol estrogens. MB-COMT is the main form in the brain, and its physiological function is to metabolize and inactivate catecholamine neurotransmitters (such as dopamine, epinephr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/06C07D407/06C07D417/06C07D311/64C09K11/06G01N21/64G01N33/52G01N33/58
CPCC07D405/06C07D407/06C07D417/06C07D311/64C09K11/06G01N21/6428G01N33/582G01N33/52C09K2211/1088C09K2211/1037C09K2211/1029
Inventor 王平杨凌王方园葛广波魏来
Owner WUXI ERYUN TECH CO LTD
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