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A ratiometric fluorescent probe for bisulfite detection and its preparation method and application

A technology of bisulfite and fluorescent probes, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of low sensitivity and low sensitivity, achieve strong anti-interference ability, and simple preparation method , the effect of high yield

Active Publication Date: 2020-11-20
HENAN UNIV OF ANIMAL HUSBANDRY & ECONOMY
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Problems solved by technology

Patent 108129428 discloses a ratio fluorescent probe for detecting bisulfite and its application. The probe is made of dansyl fluorophore as donor, (E)-2-(3-cyano-4-( 4-(Dimethylamino)styrene)-5,5-dimethylfuran-2(5H)-ylidene)malononitrile fluorophore was used as an acceptor, and a fluorescence resonance energy transfer mechanism based on piperazine linkage was constructed. A ratiometric fluorescent probe for detecting bisulfite, which is mainly used in lipid droplet localization imaging in cells, and has low sensitivity; patent CN201310213806.4 discloses a method obtained by condensation of benzindoline and aromatic aldehyde The product is a bisulfite ion fluorescent probe as a probe molecule and the technical scheme of the preparation method, but the probe only shows a specific indicator for the presence of bisulfite in aqueous solution; the use is limited and the sensitivity is not high; therefore , it is very meaningful to develop efficient and sensitive fluorescent probes for bisulfite detection

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  • A ratiometric fluorescent probe for bisulfite detection and its preparation method and application
  • A ratiometric fluorescent probe for bisulfite detection and its preparation method and application
  • A ratiometric fluorescent probe for bisulfite detection and its preparation method and application

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preparation example Construction

[0034] The preparation route and the method of intermediate CBP in the embodiment are as follows:

[0035]

[0036] ① Synthesis of CBP-1: Dissolve piperazine (6 g, 69 mmol) in 30 mL DMF, add potassium carbonate (9.51 g, 69 mmol), stir for 15 minutes, then add p-fluoroacetophenone to the mixture (3.2 g, 2.298 mmol), refluxed overnight at 80°C, after the reaction was complete, the solvent was removed under reduced pressure, dissolved in dichloromethane, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain CBP-1 , Yield: 55%;

[0037] ② Synthesis of CBP: Weigh 4-diethylaminosalicylaldehyde (193.1 mg, 1 mmol) and CBP-1 (204.1 mg, 1 mmol) in a 25 ml round bottom flask, add 3 mL of concentrated sulfuric acid, 90 °C Heat and stir for 6 h under the conditions; after the reaction is completed, cool to room temperature, add the reaction solution dropwise to 30 mL of ice water, and then add 7-8 drops ...

Embodiment 1

[0039] The preparation method of the ratiometric fluorescent probe used for bisulfite detection in this embodiment:

[0040]The intermediate CBP (181 mg, 0.5 mmol) and triethylamine (70 mg, 0.5 mmol) were dissolved in 20 mL of acetonitrile and stirred for 10 minutes, and 4-chloro-7-nitrobenzofurazan (100 mg, 0.5 mmol) and continued to stir for 10 hours. Spin the reaction solution in the step to remove acetonitrile, redissolve it with dichloromethane (20 mL), wash 3 times with 20 mL of saturated sodium chloride solution, separate the organic phase, dry the organic phase with anhydrous sodium sulfate, filter, and reduce Concentrated under reduced pressure, separated by column chromatography (DCM / MeOH=45 / 1) to obtain 131.3 mg of a dark blue solid, the fluorescent probe CBP-N, with a yield of 50%.

[0041] NMR determination of fluorescent probe CBP-N: 1 H NMR (DMSO, 400 MHz) δ 1.24 (t, J = 6.0Hz, 6H), 3.66 (d, J = 4.0 Hz, 4 H), 3.98 (s, 4 H), 4.38 (s, 4 H), 6.58 (d, J = 8.0...

Embodiment 2

[0044] The preparation method of the ratiometric fluorescent probe used for bisulfite detection in this embodiment:

[0045] The intermediate CBP (181 mg, 0.5 mmol) and triethylamine (140 mg, 1 mmol) were dissolved in 20 mL of acetonitrile and stirred for 15 minutes, and 4-chloro-7-nitrobenzofurazan (200 mg, 1.5 mmol) and continued stirring for 18 hours. Spin the reaction solution in the step to remove acetonitrile, redissolve it with dichloromethane (20 mL), wash 3 times with 20 mL of saturated sodium chloride solution, separate the organic phase, dry the organic phase with anhydrous sodium sulfate, filter, and reduce Concentrated under reduced pressure and separated by column chromatography (DCM / MeOH=40 / 1) to obtain 157.6 mg of a dark blue solid, the fluorescent probe CBP-N, with a yield of 60%.

[0046] NMR determination of fluorescent probe CBP-N: 1 H NMR (DMSO, 400 MHz) δ 1.24 (t, J = 6.0Hz, 6H), 3.66 (d, J = 4.0 Hz, 4 H), 3.98 (s, 4 H), 4.38 (s, 4 H), 6.58 (d, J =...

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Abstract

The invention discloses a preparation method and application of a ratio-type fluorescent probe for bisulfite detection. A molecular formula of the probe is C29H29N6O4<+>, abbreviated as: CBP-N, and recognition characteristics of the probe CBP-N with small molecule substances such as metal ions, common amino acids, active oxygen, and active sulfur in a CH3CN-PBS solution are studied by a fluorescence spectrometer. The results show that the probe CBP-N has efficient and specific selectivity for bisulfite, and has relatively strong anti-interference ability, and a minimum detection limit is 18 nM. After the probe CBP-N responded to bisulfite, in a fluorescence emission spectrum, the fluorescence intensity at 549 nm is significantly enhanced, and the fluorescence intensity at 631 nm is significantly reduced, so that the ratio-type detection of bisulfite can be realized, the characteristic can overcome the interference of common factors in the environment, and the probe has relatively goodpractical application value.

Description

technical field [0001] The invention belongs to the field of organic small-molecule fluorescent probes, in particular to a ratio-type fluorescent probe for bisulfite detection and its preparation method and application. Background technique [0002] Sulfur dioxide is a common air pollutant. In neutral aqueous solution, it is easily hydrolyzed into bisulfite and sulfite. In daily production and life, sulfur dioxide and its derivatives are widely used in enzyme inhibitors, antibacterial agents, preservatives, etc. In the food industry, sulfites are widely used as preservatives in food and beverages to prevent food oxidation and bacterial growth, and to inhibit the occurrence of enzymatic and non-enzymatic browning during production and storage. However, high doses of sulfite may cause adverse reactions and acute symptoms. The World Health Organization stipulates that the threshold level of sulfite in food should be strictly controlled. Therefore, it is of great significance ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/12C09K11/06G01N21/64
CPCC07D413/12C09K11/06C09K2211/1007C09K2211/1044C09K2211/1048C09K2211/1088G01N21/64
Inventor 马志伟王川川陈晓培刘俊桃刘志景吴金松吕全建
Owner HENAN UNIV OF ANIMAL HUSBANDRY & ECONOMY
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