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Fluorescent probe for simultaneously detecting hypochlorous acid and peroxynitroso anions as well as synthesis method and application of fluorescent probe

A technology for the detection of hypochlorous acid by peroxynitroso, which is applied in the field of biological detection technology and clinical medical detection. Small side effects, good solubility effect

Active Publication Date: 2021-03-05
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, these probes have been reported only for HOCl or ONOO - single recognition, ignoring that the occurrence and development of tumors and other diseases are the result of the interaction of multiple superoxides in cells, which cannot reflect the intracellular HOCl and ONOO - Horizontal real-time and dynamic quantitative change rules, and the accuracy of repeated and step-by-step tests is low, and the system error is high
Testing for one marker alone does not determine whether the symptom is present and may lead to misdiagnosis

Method used

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  • Fluorescent probe for simultaneously detecting hypochlorous acid and peroxynitroso anions as well as synthesis method and application of fluorescent probe
  • Fluorescent probe for simultaneously detecting hypochlorous acid and peroxynitroso anions as well as synthesis method and application of fluorescent probe
  • Fluorescent probe for simultaneously detecting hypochlorous acid and peroxynitroso anions as well as synthesis method and application of fluorescent probe

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Experimental program
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Effect test

Embodiment 1

[0051] The synthetic method of the near-infrared fluorescent probe that detects hypochlorous acid and peroxynitroso anion simultaneously in the present embodiment, this synthetic method comprises the following steps:

[0052] Step 1. Commercially available 4-bromo-1,8-naphthalic anhydride (6g, 21.74mmol) and biboronic acid pinacol ester (6.631g, 26.1mmol) and potassium acetate (2.13g, 21.74mmol): palladium Catalyst (10g, 10.87mmol) was added to a 250mL round-bottomed flask, 1,4-dioxane, 10-20 times its mass, was added to the mixture, nitrogen protection, reflux at 110°C for 12h, filtration, column chromatography Compound 1 was obtained for later use (yield 89%).

[0053] Step 2. Dissolve compound 1 (2g, 6.2mmol), ammonium acetate (1.4g, 18.6mmol), potassium periodate (2.7g, 12.4mmol) in a mixed solution of an appropriate amount of acetone and water, react for 12h, filter the system , extract and retain the organic phase and spin-dry the organic phase to obtain compound 2 for ...

Embodiment 2

[0065] The synthetic method of the near-infrared fluorescent probe that detects hypochlorous acid and peroxynitroso anion simultaneously in the present embodiment, this synthetic method comprises the following steps:

[0066] Step 1, add commercially available 4-bromo-1,8-naphthalic anhydride (6g, 21.74mmol) and BoC-alkyldiamine (4g, 25mmol) into a 50mL round bottom flask, add 1,4-di Oxycycline 20mL, nitrogen protection, reflux at 110°C for 12h, filter, and obtain compound 5 for use after column chromatography (yield 92%);

[0067] Step 2, the resulting compound 5 (8.3g, 20mmol) and biboronic acid pinacol ester (6.631g, 26.1mmol) potassium acetate (2.13g, 21.74mmol): palladium catalyst (10g, 10.87mmol) was added to a 250mL round Add an appropriate amount of ethanol as a solvent in the bottom flask, protect it with nitrogen, reflux at 110° C. for 12 hours, filter, and obtain compound 6 after column chromatography (87% yield).

[0068] Step 3: Dissolve compound 6 (9.4g, 20mmol)...

Embodiment 3

[0075] The synthetic method of the near-infrared fluorescent probe that detects hypochlorous acid and peroxynitroso anion simultaneously in the present embodiment, this synthetic method comprises the following steps:

[0076] Step 1, commercially available 4-bromo-1,8-naphthalic anhydride (6g, 21.74mmol) and biboronic acid pinacol ester (6.631g, 26.1mmol) and potassium acetate (2.13g, 21.74mmol): palladium Add catalyst (10g, 10.87mmol) into a 250ml round bottom flask, add 50mL absolute ethanol as solvent, add 1,4-dioxane whose mass is 10-20 times to the mixture, nitrogen protection, 110°C Reflux for 12 h, filter, and obtain compound 1 for use after column chromatography (89% yield).

[0077] Step 2. Dissolve compound 1 (2g, 6.2mmol), ammonium acetate (1.4g, 18.6mmol), potassium periodate (2.7g, 12.4mmol) in a mixed solution of an appropriate amount of acetone and water, react for 12h, filter the system , extract and retain the organic phase and spin-dry the organic phase to o...

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Abstract

The invention relates to a fluorescent probe for simultaneously detecting hypochlorous acid and peroxynitroso anions as well as a preparation method and application of the fluorescent probe. Comparedwith the prior art, the structural formula of the fluorescent probe is shown in the specification; the fluorescent probe has better chemical and light stability, better solubility and higher hypochlorous acid and peroxynitroso selectivity; the probe is not interfered by other active oxygen, active nitrogen and other species, and laser confocal imaging experiments show that the probe has good cellpermeability and small toxic and side effects on cells and organisms.

Description

technical field [0001] The invention relates to the fields of biological detection technology and clinical medical detection, in particular to a fluorescent probe for simultaneously detecting hypochlorous acid and peroxynitroso anions and a synthesis method thereof. Background technique [0002] As a kind of reactive oxygen species, hypochlorite plays an extremely important role in the process of immunity against microbial infection and inflammation. H in living organisms 2 o 2 Under the catalysis of myeloperoxidase and chloride ions, hypochlorite is produced, which is the main source of endogenous hypochlorite. Maintaining an appropriate hypochlorite concentration is critical to many cellular functions, however studies have shown that once intracellular hypochlorite levels cannot be maintained within the normal physiological range, it may lead to a variety of diseases such as atherosclerosis Sclerosis, arthritis, rheumatoid arthritis and even tumors, so real-time monitor...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/025C09K11/06G01N21/6402G01N21/6428G01N21/6456G01N21/6486C09K2211/1029C09K2211/1037
Inventor 周义锋王志刚魏鹏许梦茵刘飞扬刘玲燕刘中宽易涛
Owner SHANGHAI INST OF TECH
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