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Bioluminescent probe for detecting sulfite as well as preparation method and application of bioluminescent probe

A technology of bioluminescence and compounds, applied in the direction of luminescent materials, chemical instruments and methods, measuring devices, etc., can solve the problems of low detection sensitivity, poor anti-interference ability, long reaction time, etc., achieve high responsiveness, broad application prospects, The effect of high sensitivity

Inactive Publication Date: 2020-05-05
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the probes used to detect sulfite are constantly developing, but there are many problems, such as: the detection limit does not meet the requirements, the detection sensitivity is low, the reaction time is long, the anti-interference ability is poor, and it cannot be used for dynamic visualization of living bodies detection etc.

Method used

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  • Bioluminescent probe for detecting sulfite as well as preparation method and application of bioluminescent probe
  • Bioluminescent probe for detecting sulfite as well as preparation method and application of bioluminescent probe
  • Bioluminescent probe for detecting sulfite as well as preparation method and application of bioluminescent probe

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Experimental program
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Embodiment 1

[0063] Embodiment 1, the preparation of the compound of the present invention (bioluminescence probe)

[0064] The synthetic route of compound of the present invention is as follows:

[0065]

[0066] Step 1: Mix and dissolve 1.2 mmol of raw material I and 1 mmol of raw material II in 20 mL of organic solvent dichloromethane, and add 2 mmol of condensing agent 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI), 2mmol organic base triethylamine (TEA), 0.1mmol catalyst 4-dimethylaminopyridine (DMAP), reacted at 0°C for 2h to generate 157mg of intermediate III with a yield of 87.3%.

[0067] Intermediate III: mp:94.0-95.4℃. 1 H NMR (400MHz, DMSO-d 6 )δ8.30(d, J=8.8Hz, 1H), 8.15(d, J=2.4Hz, 1H), 7.48(dd, J=8.8, 2.4Hz, 1H), 2.89(t, J=6.6Hz, 2H), 2.80(ddd, J=6.8, 5.6, 1.2Hz, 2H), 2.17(s, 3H). 13 C NMR (101MHz, DMSO-d 6 )δ206.75, 171.22, 150.27, 149.34, 137.48, 136.26, 125.22, 123.12, 115.82, 113.24, 37.48, 29.45, 27.83.

[0068] Step 2: Dissolve 1mmol of inte...

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Abstract

The invention provides a bioluminescent probe for detecting sulfite as well as a preparation method and application of the bioluminescent probe. The probe is a compound shown as a formula I (See the specification for reference), or salt thereof, or a stereoisomer thereof, wherein n is an integer from 1 to 5, and R1, R2, R3, R4, R5 and R6 are respectively and independently selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, halogen, hydroxyl, carboxyl, amino and nitro. The bioluminescent probe provided by the invention has high selectivity and high responsiveness to sulfite ions in sulfite, cansingly and accurately select sulfite, has very high sensitivity during detection, can detect sulfite with very low concentration, and is used for precision detection of sulfite. Meanwhile, the bioluminescent probe can also be used for carrying out dynamic visual analysis on sulfite accumulation caused by exogenous sulfite and sulfite oxidase deficiency at a living body level, is beneficial to clinical detection of sulfite, and has a wide application prospect.

Description

technical field [0001] The invention belongs to the technical field of biological detection, and in particular relates to a bioluminescent probe for detecting sulfite, a preparation method and application thereof. Background technique [0002] Sulfite is a kind of food additive that has been widely used in the world for a long time. It can be used as food bleaching agent and preservative; it can inhibit non-enzymatic browning and enzymatic browning, prevent food browning, and keep fruits from black It can also prevent fresh shrimp from forming black spots; it is also a very effective antibacterial agent in acidic medium. Since sulfite plays an important role in food storage, it is widely used in the food field. Therefore, sulfite can easily enter the human body along with food. Although there is a sulfite oxidase in the human body, it can catalyze the combination of sulfite and oxygen to generate non-toxic SO 4 2- ; However, if the content of sulfite in the human body is...

Claims

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Application Information

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IPC IPC(8): C07D277/62C07D277/68C09K11/06G01N21/64
CPCC07D277/62C07D277/68C09K11/06C09K2211/1037G01N21/6428G01N21/643G01N21/6486
Inventor 张雨薇柯博文李敏勇康婷冯萍
Owner WEST CHINA HOSPITAL SICHUAN UNIV