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Ratio type fluorescent probe substrate for cytochrome oxidase CYP1A and application thereof

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

Active Publication Date: 2016-01-06
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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  • Ratio type fluorescent probe substrate for cytochrome oxidase CYP1A and application thereof
  • Ratio type fluorescent probe substrate for cytochrome oxidase CYP1A and application thereof
  • Ratio type fluorescent probe substrate for cytochrome oxidase CYP1A and application thereof

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 and dry in vacuo N-(3-carboxypropyl)-4-bromo-1,8-naphthalimide was obtained as a beige solid 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 absor...

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, precipitate a large amount of solid, filter and dry in vacuo N-(3-carboxypentyl)-4-bromo-1,8-naphthalimide was obtained as a beige solid 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-carboxypent...

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, and dry in vacuo N-(4-carboxyphenyl)-4-bromo-1,8-naphthalimide was obtained as a beige solid 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...

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Abstract

The invention discloses a ratio type fluorescent probe substrate for cytochrome oxidase CYP1A and an application thereof. The specific probe substrate has a hydroxynaphthalimide alkane acid structure and can be used for determining the CYP1A enzymatic activity in a biosystem. A flow for determining the CYP1A enzymatic activity comprises the following steps: selecting a hydroxynaphthalimide alkane acid demethylation reaction as a probe reaction, and determining the CYP1A enzymatic activity in various biological samples by quantitatively detecting the production amount of demethylation metabolites in a unit time. The ratio type fluorescent probe substrate disclosed by the invention can be used for quantitative evaluation for the CYP1A enzymatic activity in biological samples of different species and different individual sources and for quantitative determination for the CYP1A enzymatic activity in different-source animal tissue cell culture fluids and cell prepared products, so as to realize evaluation for the medicine disposition capacity of the important medicine metabolizing enzyme CYP1A. In addition, the probe reaction can also be used for rapidly screening a CYP1A inhibitor in vitro and evaluating the inhibition capacity of the inhibitor.

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 Applications(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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