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Cytochrome oxidase CYP1A1 specific fluorescent probe, preparation method and applications thereof

A CYP1A1 and cytochrome technology, applied in the field of biomedicine, can solve problems such as large quantitative errors, biological matrix interference, and low selectivity of single enzymes, and achieve the effect of easy detection sensitivity

Inactive Publication Date: 2017-08-08
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These known fluorescent substrates are all off-on probes, the selectivity of the single enzyme is not high and they are easily interfered by the biological matrix, resulting in large quantitative errors

Method used

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  • Cytochrome oxidase CYP1A1 specific fluorescent probe, preparation method and applications thereof
  • Cytochrome oxidase CYP1A1 specific fluorescent probe, preparation method and applications thereof
  • Cytochrome oxidase CYP1A1 specific fluorescent probe, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1. Synthesis of N-n-butyl-4-chloroethoxy-1,8-naphthalimide

[0041] (1) Synthesis of compound N-n-butyl-4-bromo-1,8-naphthalimide

[0042] Add 4.2mmol of n-butylamine to 50ml of ethanol solution containing 1g (3.61mmol) of 4-bromo-1,8 naphthalene anhydride, react overnight at 70-80°C, add 200ml of water, precipitate a large amount of solid, filter, and dry in vacuo to obtain Beige solid N-n-butyl-4-bromo-1,8-naphthalimide, yield 80-90%.

[0043] (2) Synthesis of compound N-n-butyl-4-methoxy-1,8-naphthalimide

[0044] Put 800mg of N-n-butyl-4-bromo-1,8-naphthalimide and 2.54g of potassium carbonate in a 100ml single-necked bottle, add 30ml of methanol, react at 60-70°C overnight, cool down, and a large amount of yellow solid precipitates , filtered, washed with a large amount of water, and dried in vacuo to obtain N-n-butyl-4-methoxy-1,8-naphthalimide as a yellow solid with a yield of 80-90%.

[0045] (3) Synthesis of N-n-butyl-4-hydroxyl-1,8-naphthalimide

...

Embodiment 2

[0050] Example 2. Synthesis of N-ethyl-4-chloroethoxy-1,8-naphthalimide

[0051] (1) Synthesis of compound N-ethyl-4-bromo-1,8-naphthalimide

[0052] Add 4.2mmol of ethylamine to 50ml of ethanol solution containing 1g (3.61mmol) of 4-bromo-1,8 naphthalene anhydride, react overnight at 70-80°C, add 200ml of water, precipitate a large amount of solid, filter, and dry in vacuo to obtain beige N-ethyl-4-bromo-1,8-naphthalimide as a colored solid with a yield of 80-90%.

[0053] (2) Synthesis of compound N-ethyl-4-methoxy-1,8-naphthalimide

[0054] Put 800mg of N-ethyl-4-bromo-1,8-naphthalimide and 2.54g of potassium carbonate in a 100ml single-necked flask, add 30ml of methanol, react at 60-70°C overnight, cool down, and a large amount of yellow solid precipitates out. Filter, wash with a large amount of water, and dry in vacuo to obtain N-ethyl-4-methoxy-1,8-naphthalimide as a yellow solid with a yield of 80-90%.

[0055] (3) Synthesis of N-ethyl-4-hydroxyl-1,8-naphthalimide ...

Embodiment 3

[0059] Example 3. Synthesis of N-hexyl-4-chloroethoxy-1,8-naphthalimide

[0060] (1) Synthesis of compound N-hexyl-4-bromo-1,8-naphthalimide

[0061] Add 4.2mmol of hexylamine to 50ml of ethanol solution containing 1g (3.61mmol) of 4-bromo-1,8 naphthalene anhydride, react overnight at 70-80°C, add 200ml of water, precipitate a large amount of solid, filter, and dry in vacuo to obtain beige Color solid N-hexyl-4-bromo-1,8-naphthalimide, yield 80-90%.

[0062] (2) Synthesis of compound N-hexyl-4-methoxy-1,8-naphthalimide

[0063] Put 800mg of N-hexyl-4-bromo-1,8-naphthalimide and 2.54g of potassium carbonate in a 100ml single-necked bottle, add 30ml of methanol, react overnight at 60-70°C, cool down, a large amount of yellow solid precipitates, filter , washed with a large amount of water, and dried in vacuum to obtain N-hexyl-4-methoxy-1,8-naphthalimide as a yellow solid with a yield of 80-90%.

[0064] (3) Synthesis of N-hexyl-4-hydroxyl-1,8-naphthalimide

[0065] Put 300m...

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Abstract

The invention relates to a cytochrome oxidase CYP1A1 specific fluorescent probe, a preparation method and applications thereof, wherein the specific probe substrate has a 4-hydroxynaphthalimide structure, and can be used for determining the CYP1A1 enzyme activity in a biological system. The CYP1A1 enzyme activity determination process comprises: selecting a 4-hydroxynaphthalimide dechloroethylation reaction as a probe reaction, and determining the activity of the CYP1A1 enzyme in various biological samples by quantitatively detecting the generation amount of the dechloroethylation metabolites per unit time. According to the present invention, the cytochrome oxidase CYP1A1 specific fluorescent probe can be used for the quantitative evaluation of the CYP1A1 enzyme activity in biological samples having different species and different individual sources, and the quantitative determination of the CYP1A1 enzyme activity in animal culture cell culture liquids and cell preparation products from different origins so as to evaluate the drug treatment capacity of the important drug metabolic enzyme CYP1A1; and the probe reaction can further be used for rapidly screening inhibitors and inducers of CYP1A1 in vitro and evaluating the inhibition ability.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and in particular relates to a kind of cytochrome oxidase CYP1A1 specific fluorescent probe and its preparation method and application. Background technique [0002] Cytochrome P450 (cytochrome P450, P450) enzyme, also known as mixed-function oxidase or microsomal monooxygenase, is the most important drug-metabolizing enzyme in the body. P450 participates in the synthesis and metabolism of human cholesterol, hormones, fatty acids, vitamins and other endogenous substances, plays an important role in maintaining normal physiological functions of the human body, and also participates in the biotransformation of most foreign substances, about 70% of drugs (including The major clearance of most clinical drugs and pesticides) is mediated by P450. The phase I reaction catalyzed by cytochrome P450 enzymes is a key step in the metabolism of compounds in vivo, because this step is usually the rate-lim...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D221/14C12Q1/26G01N21/64
Inventor 杨凌戴子茹崔京南葛广波冯磊宁静
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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