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The ratiometric fluorescent probe substrate of cytochrome oxidase cyp1a and its application

A cytochrome and fluorescent probe technology, applied in the field of ratiometric fluorescent probe reaction, can solve the problems of large quantitative error, biological matrix interference, low selectivity of single enzyme, etc., and achieve a simple and easy synthesis process and low detection cost. Effect

Active Publication Date: 2017-08-04
ZHANGJIAGANG IND TECH RES INST CO LTD DALIAN INST OF CHEM PHYSICS CHINESE ACADEMY OF SCI +1
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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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  • The ratiometric fluorescent probe substrate of cytochrome oxidase cyp1a and its application
  • The ratiometric fluorescent probe substrate of cytochrome oxidase cyp1a and its application
  • The ratiometric fluorescent probe substrate of cytochrome oxidase cyp1a and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthetic route of N-(3-carboxypropyl)-4-methoxy-1,8-naphthalimide

[0039] (1) Synthesis of Compound 1

[0040] Add 4.2mmol of 4-aminobutyric acid 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, vacuum Drying gave beige solid N-(3-carboxypropyl)-4-bromo-1,8-naphthalimide with a yield of 80-90%.

[0041] (2) Synthesis of Compound 2

[0042] Put 800mg of compound 1 and 2.54g of potassium carbonate in a 100ml single-necked bottle, add 30ml of methanol, react at 60-70°C overnight, cool, adjust the pH to acidic with 1M hydrochloric acid, a large amount of yellow solid precipitates, filter, wash with a large amount of water, Vacuum drying gave N-(3-carboxypropyl)-4-methoxy-1,8-naphthalimide as a yellow solid with a yield of 80-90%.

[0043] The structures of compounds 1 and 2 are as follows Figure 9 As shown, the UV absorption spectrum ...

Embodiment 2

[0046] Synthesis of N-(carboxypentyl)-4-methoxy-1,8-naphthalimide

[0047] (1) Synthesis of compound N-(3-carboxypentyl)-4-bromo-1,8-naphthalimide

[0048] Add 4.2mmol of 6-aminocaproic acid 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, a large amount of solid precipitates, filter, vacuum Drying gave beige solid N-(3-carboxypentyl)-4-bromo-1,8-naphthalimide with a yield of 80-90%.

[0049] (2) Synthesis of compound N-(3-carboxypentyl)-4-methoxy-1,8-naphthalimide

[0050] Put 800mg of compound N-(3-carboxypentyl)-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, and cool , the pH was adjusted to acidic with 1M hydrochloric acid, a large amount of yellow solid was precipitated, filtered, washed with a large amount of water, and dried in vacuo to obtain yellow solid N-(3-carboxypentyl)-4-methoxyl...

Embodiment 3

[0054] Synthesis of N-(4-carboxyphenyl)-4-methoxy-1,8-naphthalimide

[0055] (1) Synthesis of compound N-(4-carboxyphenyl)-4-bromo-1,8-naphthalimide

[0056] Add 4.2mmol of 4-aminobenzoic acid to 50ml of acetic acid solution containing 1g (3.61mmol) of 4-bromo-1,8 naphthalene anhydride, react overnight at 100-110°C, filter while hot, wash the filter cake with acetic acid, vacuum Drying gave beige solid N-(4-carboxyphenyl)-4-bromo-1,8-naphthalimide with a yield of 30-40%.

[0057] (2) Synthesis of compound N-(4-carboxyphenyl)-4-methoxy-1,8-naphthalimide

[0058] Put 800 mg of compound N-(4-carboxyphenyl)-4-bromo-1,8-naphthoimide and 2.54 g of potassium carbonate in a 100 ml single-necked bottle, add 30 ml of methanol, and react overnight at 60-70 ° C, Cool, adjust the pH to acidic with 1M hydrochloric acid, precipitate a large number of yellow solids, filter, wash with water, and dry in vacuo to obtain yellow solid N-(4-carboxyphenyl)-4-methoxy-1,8-naphthalene Amine, 60-70% ...

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Abstract

Disclosed are a ratio-type fluorescent probe substrate of cytochrome oxidase CYP1A and a use thereof, which belong to the technical field of biomedicine. The specific probe substrate has a structure of a hydroxy-naphthalimide-alkanoic acid, which can be used for determining the enzyme activity of the CYP1A in a biosystem. The flow process for determining the enzyme activity of CYP1A is as follows: selecting the demethylation of hydroxy-naphthalimide-alkanoic acids as the probe reaction; and the enzyme activity of the CYP1A in a variety of biological samples were determined by quantitative detection of the amount of produced demethylation metabolic product in unit time. The present invention can be used for the quantitative evaluation of the enzyme activity of CYP1A in the biological samples from various individuals, various individual sources, and for the quantitative determination of the enzyme activity of CYP1A in animal tissue cell culture media and the cell preparations from different sources, so as to achieve the evaluation for the ability of the drug disposition of the important drug metabolic enzyme CYP1A. Furthermore, the probe reaction can also be used for rapid screening of the inhibitor of CYP1A in vitro and evaluating the inhibiting ability thereof.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and in particular relates to a ratio-type fluorescent probe reaction of cytochrome oxidase CYP1A and its application. Background technique [0002] Cytochrome P450 (cytochrome P450, P450 enzyme) superfamily is the most important drug-metabolizing enzyme in the body, and the main clearance of about 60% of drugs (including most clinical drugs and pesticides) is mediated by CYP . The cytochrome P450 enzyme system is a protein superfamily, a large class of heme-containing proteins, and the complex formed with CO in the reduced state has a maximum absorption peak at 450nm. Because the phase I reaction catalyzed is a key step in the metabolism of compounds in vivo, because this step is usually the rate-limiting step for drug clearance from the body, which can affect the kinetic characteristics of the compound, such as half-life and clearance rate, and the activity of P450 enzymes often varies with...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D221/14C12Q1/26G01N21/64
CPCC07D221/14C09K11/06C12Q1/26
Inventor 杨凌戴子茹崔京南葛广波冯磊宁静
Owner ZHANGJIAGANG IND TECH RES INST CO LTD DALIAN INST OF CHEM PHYSICS CHINESE ACADEMY OF SCI
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