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Bisdansylhistidine and its application

A bisdansyl histidine and solution technology, applied in the field of the new compound bisdansyl histidine, can solve the problems of difficult detection of metal ions, difficulty in real-time detection, poor water solubility of probes, etc. Achieve the effect of good water solubility, high accuracy and high sensitivity

Inactive Publication Date: 2016-07-06
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These testing methods have a common disadvantage in that they require complex and diverse sample preparation and sophisticated experimental instruments, resulting in high analysis costs, and it is difficult to achieve real-time detection
The other is the fluorescent probe method to identify metal ions. In fluorescent probes, conjugated aromatic rings are often used as fluorescent light-emitting groups, which can easily lead to poor water solubility of the probe and make it difficult to detect metal ions in aqueous solution.

Method used

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  • Bisdansylhistidine and its application
  • Bisdansylhistidine and its application
  • Bisdansylhistidine and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the synthesis of bisdansyl histidine

[0039] The synthetic route of bis dansyl histidine is as follows:

[0040]

[0041] 1) Add 0.1245g histidine (0.65mmol) into a round bottom flask, take 15.0ml of sodium bicarbonate solution with a concentration of 0.10mol / L to dissolve it, and put it in an ice-salt bath to cool for 10min;

[0042] 2) Dissolve 0.035g of dansyl chloride (0.13mmol) in 5.0mL of acetonitrile, and add the solution of dansyl in acetonitrile to the above histidine solution dropwise with a separatory funnel, and stir the solution while adding. The reaction system was stirred and reacted in the ice-salt bath for 30 minutes, then withdrawn from the ice-salt bath, and continued to react at room temperature for 3 hours. During the reaction, the reaction progress was monitored by thin layer chromatography (TLC) until the reaction was completed. ;

[0043] 3) The reaction mixture was distilled out of acetonitrile by vacuum distillation, and t...

Embodiment 2

[0046] Embodiment 2: iron ion concentration detection method

[0047] (1) Effect of pH value on recognition of iron ions by bisdansylhistidine

[0048] Add bisdansyl histidine to aqueous solutions with different pH values, and configure different pH values ​​but the concentration is 2.0×10 -6 mol / L bisdansyl histidine solution, record the fluorescence intensity values ​​respectively, and then add an equal amount of FeCl 3 solution, making Fe 3+ 2.0×10 -5 mol / L, calculated by adding Fe 3+ After the difference of fluorescence intensity (excitation wavelength is 330nm, emission wavelength is 501nm), and draw a graph, such as image 3 as shown, image 3 Add Fe for bisdansylhistidine at pH from 2.5 to 10.35 3+ Change value of fluorescence intensity before and after, where I 0 Represents no Fe 3+ The fluorescence intensity value of bisdansylhistidine under the excitation wave (330nm) in the presence of I represents the presence of Fe 3+ Fluorescence intensity values ​​of ...

Embodiment 3

[0065] Example 3: Fluorescence recovery of bisdansylhistidine

[0066] After continuous experimental exploration, it was found that bisdansyl histidine and Fe 3+ After adding a certain amount of sodium phosphate to the system after the action, the fluorescence intensity of bisdansyl histidine can be recovered to a large extent, such as Figure 9 , where a represents the fluorescence spectrum of the bisdansyl histidine solution, and b represents the addition of FeCl to a3 solution, making Fe 3+ The concentration is 2.0×10 -5 mol / L fluorescence spectrum, c represents adding 1.0×10 -4 Fluorescence spectrum after mol / L sodium phosphate.

[0067] From Figure 9 It can be seen that when adding Fe 3+ When sodium phosphate is added to 5 times the amount (the multiple of the amount of the substance), the fluorescence intensity of the dansylhistidine solution can basically return to the initial state. This shows that dansylhistidine is Fe 3+ The fluorescent probes have good rev...

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Abstract

The invention discloses a new compound bisdansyl histidine and its preparation method and application. Its chemical formula is shown in formula I: It can be used as a fluorescent probe for iron ion detection; A method for recovering fluorescence after amino acid recognizes iron ions; bisdansyl histidine has good water solubility, is easy to make into an aqueous solution and has stable fluorescence, and can easily detect the concentration of iron ions in aqueous solution; bisdansyl histidine is a Highly sensitive fluorescent probe for iron ions, with a detection limit of 2.0×10-7 mol / L for iron ions, can identify iron ions at a pH of 2.50-10.35, and common metal ions will not affect bisdansyl The specific recognition of histidine to iron ions; the bisdansyl histidine is used as a fluorescent probe of iron ions under acidic conditions, has the characteristics of wide application range, strong recognition and good accuracy, and is suitable for popularization and application.

Description

technical field [0001] The invention relates to a new compound bisdansyl histidine and its application. Background technique [0002] Iron is an extremely abundant transition metal element in biological systems and an essential element in biological systems, playing a very important role in the metabolism of organisms. In organisms, ferric iron has the function of transporting heme, and at the same time it is a cofactor for many enzyme reactions. The lack of iron in organisms will cause anemia, liver and kidney damage, diabetes and neonatal failure and other diseases. The detection methods of iron ions generally include atomic absorption spectroscopy, plasma emission spectroscopy, electrochemical methods, colorimetry, gas chromatography, biological and nano sensor means. A common disadvantage of these testing methods is that they require complex and diverse sample preparation and sophisticated experimental instruments, resulting in high analysis costs, and it is difficult t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/64C09K11/06G01N21/64
CPCC07D233/64C09K11/06C09K2211/1011C09K2211/1014C09K2211/1044G01N21/643G01N2021/6432
Inventor 马立军邓乐芳赵美丽李煦田唐健
Owner SOUTH CHINA NORMAL UNIVERSITY