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Fluorescent probe adopting Schiff base type structure as well as preparation method and applications of fluorescent probe

A fluorescent probe and Schiff base-type technology, applied in the field of fluorescent probes, can solve problems such as poor repeatability of test results, complex electrode manufacturing process, unfavorable clinical testing, etc., and achieve simple preparation methods, strong anti-interference ability, and selectivity Good results

Active Publication Date: 2018-11-20
YANCHENG TEACHERS UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these detection methods have more or less deficiencies, such as poor enzyme stability, complicated electrode manufacturing process, poor repeatability of test results, etc., which are not conducive to clinical detection.

Method used

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  • Fluorescent probe adopting Schiff base type structure as well as preparation method and applications of fluorescent probe
  • Fluorescent probe adopting Schiff base type structure as well as preparation method and applications of fluorescent probe
  • Fluorescent probe adopting Schiff base type structure as well as preparation method and applications of fluorescent probe

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preparation example Construction

[0031] Another typical embodiment of the present invention provides a method for preparing a fluorescent probe with the above-mentioned Schiff base structure, the method comprising the steps of: dissolving thiosemicarbazide in absolute ethanol, dripping Add salicylaldehyde solution, control the internal temperature at 75-80°C and heat to reflux to make it fully react. After the reaction is completed, the reaction solution is cooled, and vacuum filtration is performed to filter the solution to retain the filter cake, which is washed with absolute ethanol and dried to obtain The solid is the fluorescent probe, and its reaction formula is:

[0032]

[0033] Wherein, R=H, Br or Cl. According to the method, different substituted salicylaldehyde and thiosemicarbazide can be heated and refluxed in one step to obtain the product, the preparation method is simple, and the reaction process is easy to control.

[0034] Referring to Example 4, the above-mentioned fluorescent probe wit...

Embodiment 1

[0039] Synthesis of Probe S1

[0040] Sonically dissolve thiosemicarbazide (0.182g, 2mmol) in 5mL of absolute ethanol, add dropwise a solution of salicylaldehyde (0.244g, 2mmol) in an oil bath (85-90°C) (dissolved in 10mL of absolute ethanol), Use magnetic force to continuously stir to make it fully react, control the internal temperature at 75-80°C, reflux for 4 hours, use TLC plate to spot the plate every hour, monitor the reaction progress, stop the reaction after the reaction is completed, and let the temperature of the reaction solution drop to room temperature , a large amount of solids were produced at the bottom of the round bottom flask, vacuum filtration was performed, the solution was filtered to retain the filter cake, washed 3-4 times with absolute ethanol, impurities were washed away, and the solid obtained by drying was probe S1, and the yield was 78.6% . White powder with a melting point of 191-192°C. 1 H NMR (400MHZ, DMSO-d 6 ):δ11.38(s,1H),9.88(s,1H),8.37(...

Embodiment 2

[0043] Synthesis of probe S2

[0044] Ultrasonically dissolve thiosemicarbazide (0.227g, 2.5mmol) in 5mL of absolute ethanol, add dropwise 5-bromosalicylaldehyde (0.5g, 2.5mmol) solution (with 10mL Dissolve in absolute ethanol), use magnetic force to stir continuously to make it fully react, control the internal temperature at 75-80°C, reflux for 4 hours, use TLC plate to spot the plate every hour, monitor the reaction progress, stop the reaction after the reaction is completed, and make the reaction The temperature of the liquid drops to room temperature, and a large amount of solids are produced at the bottom of the round-bottomed flask. Perform vacuum filtration, filter the solution and retain the filter cake, wash with absolute ethanol 3-4 times, wash away impurities, and dry to obtain a solid that is probe S2 , and the yield was 82.9%. White powder with a melting point of 239-241°C. 1 H NMR (400MHZ, DMSO-d 6 ):δ11.43(s,1H),10.24(s,1H),8.29(s,1H),8.21(s,1H),8.16(s,2H),7...

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Abstract

The invention relates to a fluorescent probe adopting a Schiff base type structure. The structural formula of the fluorescent probe is shown in the description; and R is any one of H, Br and Cl. Thiosemicarbazide is dissolved in absolute ethyl alcohol, a salicylaldehyde solution is dropped under the temperature condition of 85-90 DEG C, the inner temperature is controlled to be within 75-80 DEG C,the reflux is heated for sufficient reaction, after the reaction is completed, a reaction liquid is cooled and is subjected to reduced-pressure suction filtration, a solution is filtered out, a filter cake is reserved and is washed with the absolute ethyl alcohol, and a solid obtained after drying is the fluorescent probe. Specific recognition of D-3-hydroxybutyric acid can be realized by the aidof the fluorescent probe, fluorescence can be produced, when the D-3-hydroxybutyric acid is detected with the fluorescent spectrometry, the selectivity is high, the anti-jamming capability is high, the sensitivity is high, and a reagent can be prepared from the fluorescent probe and used for detecting the D-3-hydroxybutyric acid in blood, the body fluid or urine.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to a fluorescent probe for detecting D-3-hydroxybutyric acid and its preparation method and application. Background technique [0002] Diabetes has become the third chronic non-communicable disease that seriously endangers human health after cardiovascular and cerebrovascular diseases and tumors. Diabetic ketoacidosis (DKA) is one of the most common acute complications of diabetes, and ketone bodies are substances that cause diabetic ketoacidosis. Ketone bodies produced during human metabolism include D-3-hydroxybutyric acid (78%), acetoacetate (20%), and acetone (2%). D-3-hydroxybutyric acid is the main component of ketone bodies. The medium content is high and relatively stable, without interference from hemolysis, jaundice, and lipemia, and can accurately reflect the level of ketone body content in the body. Studies have shown that the concentration of D-3-hydroxybutyric acid in serum is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C335/40C09K11/06G01N21/64
CPCC07C335/40C09K11/06C09K2211/1007G01N21/6428G01N21/6486
Inventor 王金胡晓卢斌金文彬严燚宇仇永富张天丽崔刚
Owner YANCHENG TEACHERS UNIV