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Fluorescent probe for detecting nitroreductase and preparation method and use thereof in enzymatic reaction

a fluorescent probe and nitroreductase technology, applied in the field of industrial analysis and detection, can solve the problems of complex post-treatment, harmful to human health, and complicated technological process, and achieve significant fluorescence-enhancement effect, long emission wavelength, and good structural stability

Active Publication Date: 2021-02-18
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention introduces a fluorescent probe that can detect nitroreductase, a key enzyme in industrial reactions. This probe has low fluorescence but is greatly increased in the presence of nitroreductase, allowing for sensitive and accurate detection. Additionally, the probe has a long emission wavelength and good stability, making it suitable for harsh and complicated environments in industrial reactions. Overall, this invention provides a valuable tool for the development of enzymatic reactions in chemical industry.

Problems solved by technology

However, owing to their carcinogenesis to human, most of the nitro compounds may cause many diseases and thus are harmful to human health.
However, these methods still have such drawbacks as complicated technological process, complex post-treatment, numerous wastes generated during the process, and high preparation cost.
However, such fluorescent probe has poor water-solubility and exhibits aggregation-caused quenching of fluorescence.
So, it is difficult to realize the detection and analysis of enzyme of high concentration and in an aqueous media.
In the meantime, the two-photon detection instruments are rather complicated and expensive, the probe's application field mainly focuses on hypoxia in cells.
The probe is not suitable for use in the aqueous media, and fluorescence quenching would easily occur when a high concentration of nitroreductase is present.
However, the probe is mainly used in the cells and unable to be applied in the detection and analysis of the concentration of enzyme in the industrial enzymatic reaction systems.

Method used

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  • Fluorescent probe for detecting nitroreductase and preparation method and use thereof in enzymatic reaction
  • Fluorescent probe for detecting nitroreductase and preparation method and use thereof in enzymatic reaction
  • Fluorescent probe for detecting nitroreductase and preparation method and use thereof in enzymatic reaction

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0042](1) 365 mg of 4′-(diphenylamino)-3-hydroxy-[1,1′-biphenyl]-4-carbaldehyde was dissolved in 10 mL of dimethyl sulfoxide, 324 mg of 1-(bromomethyl)-4-nitrobenzene was dissolved in 10 mL of tetrahydrofuran, followed by ultrasonic treatment respectively, and then they were mixed together. 1.96 g of cesium carbonate was added to perform a reaction of which a reaction temperature was maintained at 50° C. and which lasted for 5 hours. An obtained reaction mixture was cooled to room temperature and extracted with dichloromethane / deionized water, an organic phase was collected, dried and filtered, the solvent was removed by rotary evaporation, and an obtained solid was purified via a silica gel chromatographic column (an eluent used is dichloromethane / petroleum ether, V / V=2:1). A product, 405 mg of 4′-(diphenylamino)-3-((4-nitrobenzyl)oxy)-[1,1′-biphenyl]-4-carbaldehyde in yellow solid powder, was obtained (with a yield of 81%). The product was characterized by 1H-NMR, wherein 1H NMR (...

example 2

[0044](1) 365 mg of 4′-(diphenylamino)-3-hydroxy-[1,1′-biphenyl]-4-carbaldehyde was dissolved in 10 mL of dimethyl sulfoxide, 389 mg of was dissolved in 10 mL of tetrahydrofuran, followed by ultrasonic treatment respectively, and then they were mixed together. 2.64 g of cesium carbonate was added to perform a reaction of which a reaction temperature was maintained at 100° C. and which lasted for 24 hours. An obtained reaction mixture was cooled to room temperature and extracted with dichloromethane / deionized water, an organic phase was collected, dried and filtered, the solvent was removed by rotary evaporation, and an obtained solid was purified via a silica gel chromatographic column (an eluent used is dichloromethane / petroleum ether, V / V=2:1). A product, 415 mg of 4′-(diphenylamino)-3-((4-nitrobenzyl)oxy)-[1,1′-biphenyl]-4-carbaldehyde in yellow solid powder, was obtained (with a yield of 83%).

[0045](2) 265 mg of 3-(4-methylquinoline-1-bromine)propane-1-sulfonate was dissolved in...

example 3

[0047](1) 365 mg of 4′-(diphenylamino)-3-hydroxy-[1,1′-biphenyl]-4-carbaldehyde was dissolved in 10 mL of dimethyl sulfoxide, 432 mg of 1-(bromomethyl)-4-nitrobenzene was dissolved in 10 mL of tetrahydrofuran, followed by ultrasonic treatment respectively, and then they were mixed together. 3.26 g of cesium carbonate was added to perform a reaction of which a reaction temperature was maintained at 150° C. and which lasted for 48 hours. An obtained reaction mixture was cooled to room temperature and extracted with dichloromethane / deionized water, an organic phase was collected, dried and filtered, solvent was removed by rotary evaporation, and an obtained solid was purified via a silica gel chromatographic column (an eluent used is dichloromethane / petroleum ether, V / V=2:1). A product, 430 mg of 4′-(diphenylamino)-3-((4-nitrobenzyl)oxy)-[1,1′-biphenyl]-4-carbaldehyde in yellow solid powder, was obtained (with a yield of 86%).

[0048](2) 265 mg of 3-(4-methylquinoline-1-bromine)propane-1...

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Abstract

The present invention relates to a fluorescent probe for detecting nitroreductase and a preparation method and use thereof in enzymatic reactions, belonging to the field of industrial analysis and detection. The fluorescent probe is 3-(4-(2-(4′-(diphenylamino)-3-((4-nitrobenzyl)oxy)-[1,1′-biphenyl]-4-yl)vinyl)quinolin-1-ium-1-yl)propane-1-sulfonate. The fluorescent probe of the present invention, with the introduction of hydrophilic groups, sulfonate and quinolinium, the probe's hydrophilicity is enhanced, under the enzymatic catalysis of nitroreductase (NTR), 1,6-rearrangement and elimination reaction occurs, and hydroxyl group is generated. Detection and analysis of the NTR in the industrial enzymatic reactions can be realized due to the change of fluorescence which is induced by the intramolecular charge transfer (ICT) effect. This method has such advantages as easy preparation, high yield and being suitable for detecting high concentration of enzyme in the enzymatic reactions, and it shows an extensive application prospect in the field of enzyme-detection in the industrial enzymatic reaction systems.

Description

BACKGROUNDTechnical Field[0001]The present invention relates to the technical field of industrial analysis and detection, and specifically relates to a fluorescent probe for detecting nitroreductase and a preparation method and use thereof in enzymatic reaction.Description of Related Art[0002]Nitro compounds are widely used in the fields of medicine, dyes, pesticides, explosives, and etc. However, owing to their carcinogenesis to human, most of the nitro compounds may cause many diseases and thus are harmful to human health. Amine compounds are essential to the synthesis of various fine chemical products and intermediates such as pesticides, medicine, dyes, synthetic resins, surfactants, and etc., for the introduction of amino group makes the change of function of the fine chemicals possible. For example, the introduction of amino group causes a red shift in the absorption and emission spectra of the compounds, the introduction of amino group to the ortho-position of a dye chromopho...

Claims

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Application Information

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IPC IPC(8): G01N21/76C12Q1/26C07D215/14C09K11/06G01N21/64
CPCG01N21/76C12Q1/26C07D215/14G01N2021/6432G01N21/6428C09K2211/1018C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029
Inventor WU, SHUIZHUXU, LINGFENGNI, LINGZENG, FANG
Owner SOUTH CHINA UNIV OF TECH
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