Compound and method applying same for fluorescence detection of activity of monoamine oxidase

A technology of monoamine oxidase and compound, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve problems such as complex preparation

Active Publication Date: 2012-11-14
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are some methods for detecting and analyzing monoamine oxidase through fluorescent probes, their preparation is relatively complicated, and a simple and effective fluorescent probe detection method is lacking.

Method used

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  • Compound and method applying same for fluorescence detection of activity of monoamine oxidase
  • Compound and method applying same for fluorescence detection of activity of monoamine oxidase
  • Compound and method applying same for fluorescence detection of activity of monoamine oxidase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1, preparation 4-methyl-7-(1-methyl-1,2,3,6-tetrahydropyridine-4-oxyl group)-coumarin

[0037]

[0038] 0.1mmol (15.8mg) 4-bromopyridine was reacted with 0.6mmol (85.2mg) methyl iodide at 0°C for 12 hours, and 1-methyl-4-bromopyridinium salt was obtained after the reaction, and 1-methyl-4 -Bromopyridinium salt, 0.1mol (14.6mg) coumarin, 0.2mmol (10.8mg) sodium methoxide in 20ml DMF solvent, react at room temperature for 12 hours, filter the reaction solution after the reaction, take the filter cake at 0°C , carry out reduction reaction with 0.2mmol (7.2mg) sodium borohydride, add saturated NaCl aqueous solution to the reaction solution after the reaction, extract with ethyl acetate, take the organic layer and pass through drying, filtration, evaporate to dryness, obtain the crude product, the crude product carries out column layer Analysis, with the volume ratio of ethyl acetate and petroleum ether being 5:1 solution as the mobile phase, TLC tracking and c...

Embodiment 2

[0043] Example 2: Preparation of 4-allyl-7-(1-methyl-1,2,3,6-tetrahydropyridine-4-oxyl)-coumarin

[0044]

[0045] The method and conditions are the same as in Example 1, except that 0.6 mmol (85.2 mg) of methyl iodide is changed to 0.6 mmol (100.8 mg) of acryloyl iodide, and other operations and methods are the same as in Example 1 to obtain 4-ene Propyl-7-(1-methyl-1,2,3,6-tetrahydropyridine-4-oxyl)-coumarin 26.5 mg, yield 89.2%, purity 99.7%.

[0046] 1HNMR (CDCl3, 500MHz)

[0047] δ2.42-2.43(d, 3H, J=1.0Hz), 2.43-2.47(s, 2H), 2.80-2.86(t, 2H, J=5.5Hz), 3.15-3.12(s, 2H), 3.21- 3.25(d, 2H, J=6.5Hz), 5.15-5.153(t, 1H, J=3.5Hz), 5.23-5.32(m, 2H, J=4.8Hz), 5.92-6.02(m, 1H, J= 4.2Hz), 6.18-6.22(s, 1H), 6.98-7.00(d, 1H, J=2.5Hz), 7.01-7.05(m, 1H, J=3.7Hz), 7.54-7.57(d, 1H, J =9.0Hz)

[0048] 13CNMR (150MHz, CDCl3)

[0049] 26.57(CH3), 49.03(CH2), 50.39(CH2), 60.28(CH2), 76.75(C), 77.00(C), 77.26(C), 105.70(C), 106.72(C), 112.46(C), 114.87(C), 115.01(CH), 125.59(CH), 133....

Embodiment 3

[0050] Example 3 Preparation of 4-benzyl-7-(1-methyl-1,2,3,6-tetrahydropyridine-4-oxyl group)-coumarin

[0051]

[0052] The same method and conditions as in Example 1, the difference is that 0.6mmol (85.2mg) methyl iodide is changed to 0.6mol (130.8mg) benzyl iodide, and other operations and methods are the same as in Example 1 to obtain 4-benzyl iodide 7-(1-methyl-1,2,3,6-tetrahydropyridine-4-oxyl)-coumarin 31.2 mg, yield 90%, purity 99.3%.

[0053] 1HNMR (CDCl3, 500MHz)

[0054] δ2.38-2.43(m, 3H, J=1.0Hz), 2.43-2.46(d, 2H, J=2.5Hz), 2.78-2.88(s, 2H), 3.16-3.22(s, 2H), 3.72- 3.80(d, 2H, J=4.0Hz), 5.14-5.18(t, 1H, J=3.5Hz), 6.18-6.21(d, 1H, J=1.0Hz), 6.96-7.00(d, 1H, J= 1.0Hz), 7.01-7.05(m, 1H, J=4.0Hz), 7.30-7.34(t, 1H, J=2.5Hz), 7.35-7.398(t, 2H, J=7.0Hz), 7.41-7.45( d, 2H, J=7.0Hz), 7.55-7.57 (d, 1H, J=8.5Hz)

[0055] 13CNMR (150MHz, CDCl3),

[0056] δc161.04(CH), 159.37(C), 154.88(C), 152.43(C), 150.46(C), 157.92(C), 129.14(CH), 128.37(CH), 127.29(CH), 125.75(CH ...

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Abstract

The invention discloses a novel compound applicable as a fluorescence probe in the method for the fluorescence detection of the activity of monoamine oxidase, and a method for preparing the same. The fluorescence probe has the advantages of simple preparation device, convenient operation process and easily available material sources, for the material sources are commercialized; furthermore, the prepared fluorescence probe for monoamine oxidase has stable performance and high purity; when the fluorescence probe provided by the invention is applied to the method for the fluorescence detection of the activity of monoamine oxidase, compared with the conventional basic method for detecting the activity of monoamine oxidase, the method of the invention can greatly improve the accuracy, sensitivity and detection rate and reduce the time consumption to only few minutes.

Description

(1) Technical field [0001] The invention relates to a new compound, which can be used as a fluorescent probe in the fluorescence detection method of monoamine oxidase activity. (2) Background technology [0002] Monoamine oxidase is a type of mitochondrial membrane-bound enzyme, which catalyzes the oxidative deamination of amine compounds in organisms to generate corresponding aldehydes in the brain and peripheral nervous tissue. Studies have shown that during the process of metabolizing dopamine, monoamine oxidase produces endogenous substances such as free radicals and hydrogen peroxide, and its abnormal expression is closely related to Parkinson's disease and depression. In addition, the determination and analysis of monoamine oxidase activity in the blood of patients is of great value for the early diagnosis of acute and chronic hepatitis and liver cirrhosis. Therefore, finding a highly sensitive detection method for monoamine oxidase has great scientific research and c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12C07D413/12C07D417/14C07D211/74C09K11/06G01N21/64
Inventor 朱勍贾朝宋明贵
Owner ZHEJIANG UNIV OF TECH
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