Cytochrome oxidase cyp1a1 specific fluorescent probe and its preparation method and application

A CYP1A1, cytochrome technology, applied in the field of biomedicine, can solve the problems of large quantitative error, biological matrix interference, low selectivity of single enzyme, etc., and achieve the effect of easy detection sensitivity

Inactive Publication Date: 2019-10-11
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 and its preparation method and application
  • Cytochrome oxidase cyp1a1 specific fluorescent probe and its preparation method and application
  • Cytochrome oxidase cyp1a1 specific fluorescent probe and its preparation method and application

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

A kind of fluorescent probe specific for cytochrome oxidase CYP1A1 and its preparation method and application. The specific probe substrate has a 4-hydroxynaphthalimide structure, which can be used to measure the enzyme activity of CYP1A1 in biological systems. The procedure for the determination of CYP1A1 enzyme activity is as follows: the dechloroethylation reaction of 4-hydroxynaphthalimides was selected as the probe reaction, and the amount of dechloroethylated metabolites generated by the dechloroethylation metabolites was determined by quantitative detection per unit time. CYP1A1 enzyme activity in biological samples. The present invention can be used for the quantitative evaluation of CYP1A1 enzyme activity in biological samples from different species and different individual sources, as well as the quantitative determination of CYP1A1 enzyme activity in animal tissue cell culture fluid and cell preparations from different sources, in order to realize the important drug metabolism enzyme CYP1A1 Assessment of the ability to dispose of drugs. In addition, the probe reaction can also be used to quickly screen inhibitors and inducers of CYP1A1 in vitro and evaluate their inhibitory 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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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/14C09K11/06C12Q1/26G01N21/64
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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