GSH (glutathione) sensor based on Rhodamine B and preparation and application thereof

A fluorescence sensor and reaction time technology, applied in the field of biochemistry, can solve the problems of not particularly good selectivity, low buffer solution concentration, difficult synthesis and other problems, and achieve the effects of simple synthesis steps, simple synthesis methods and high sensitivity

Inactive Publication Date: 2016-06-08
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0007] (1) As in Document 1, the selectivity is not particularly good, and it also responds to Hcy and Cyst, and the effect is comparable to GSH, and the yield is not high
[0008] (2) As in Document 2, the concentration of the buffer solution is too low, only 0.1mM
Difficult to test under neutral conditions
[0009] The above-mentioned defects have caused so far that it is difficult to obtain a GSH sensor preparation method with simple synthesis, high yield and good selectivity by applying existing processes.

Method used

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  • GSH (glutathione) sensor based on Rhodamine B and preparation and application thereof
  • GSH (glutathione) sensor based on Rhodamine B and preparation and application thereof
  • GSH (glutathione) sensor based on Rhodamine B and preparation and application thereof

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Experimental program
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preparation example Construction

[0037] A kind of preparation method of the GSH fluorescence sensor based on Rhodamine B of the present invention comprises the following steps:

[0038] In the first step, rhodamine B and excess ethylenediamine were refluxed in absolute ethanol for more than 12 hours. After the reaction was completed, the solvent was removed under reduced pressure, extracted, and separated on a silica gel column to finally obtain a light yellow powder, that is, compound 2.

[0039] The structure of compound 2 is as follows:

[0040] ;

[0041] In the second step, 3,5-diaminobenzoic acid and maleic anhydride were refluxed in chloroform for 20 hours. After the reaction was completed, the solvent was removed by filtration, and the filter cake was dried to obtain a yellow-green powder, which was mixed with anhydrous sodium acetate in acetic anhydride After the reaction was completed, the reaction solution was poured into ice water and stirred for 1 hour, then the solvent was removed by filtrati...

Embodiment 1

[0048] Synthesis of embodiment 1 fluorescent chemical sensor

[0049] 1. Synthesis of compound 2

[0050] Rhodamine B (960mg, 2mmol) and ethylenediamine (1.3ml, 20mmol) were dissolved in absolute ethanol (40ml), the reaction temperature was controlled at 80°C, and the reaction time was 12h. After the reaction was completed, the solvent was removed under reduced pressure, and extracted , separated by silica gel column to obtain light yellow solid (880mg, 92%). Compound 2 1 HNMR, 13 CNMR respectively as figure 1 , figure 2 shown.

[0051] 2. Synthesis of compound 3

[0052] 3,5-Diaminobenzoic acid (200mg, 1.31mmol) and maleic anhydride (385mg, 3.93mmol) were refluxed in chloroform for 20h. After the reaction, the solvent was removed by filtration, and the solid was dried to obtain a yellow-green solid, which was reacted with anhydrous sodium acetate (35.1 mg, 0.43 mmol) in acetic anhydride for 2 h at 100 °C. After the reaction, the mixture was added to ice water and sti...

Embodiment 2

[0057] Embodiment 2 Fluorescence selection performance test

[0058] GSH fluorescent sensor 5 has good solubility in ethanol. It has been verified that compound 5 can be dissolved in EtOH:HEPES (0.6mM, pH=7.2) = 3:2 mixture, and 500ml of this solution was prepared as a stock solution (pH =7.2).

[0059] Precise configuration of GSH fluorescence sensor 5 as 1×10 -3 mol / LEtOH-H 2 O mixed solution (3 / 2, V / V), the concentration of amino acids GSH, Cys, Hcy, Lys, Ser, Gln, Gly, etc. is 5×10 -3 mol / L aqueous solution, and EtOH:HEPES (0.6mM, pH=7.2, 3 / 2, V / V) solution.

[0060] Fluorescent selectivity experiments such as Figure 6 As shown, take 3ml stock solution and place it in the liquid pool, add 120uLGSH to the solution of fluorescence sensor 5, measure its initial fluorescence intensity value, then add 120uL of various amino acid solutions prepared respectively, and measure its stable fluorescence intensity. Observed Figure 7 It can be seen that compound 5 has an obvious...

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Abstract

The invention discloses a GSH (glutathione) fluorescent sensor based on Rhodamine B and preparation and application thereof. Rhodamine B is used as a precursor to synthesize a target product: N-(2-(3'-6'-bis(diethylamino)-3-oxo-spiro[isoindoline-1,9'-xanthene]-2-ethyl)-3,5-bis(2,5-dioxo-3,4-pyrroline)benzamide. The invention provides application of the target product in detecting glutathione, it is discovered that the target product can well detect the glutathione, materials used herein are easy to obtain, synthetic steps are simple, post-treatment is also convenient, and large-scale production is easy to implement.

Description

technical field [0001] The invention belongs to the field of biochemistry, and in particular relates to a rhodamine B-based GSH fluorescence sensor, preparation and application. Background technique [0002] Glutathione (GSH) is widely found in animals and plants, and plays an important role in living organisms. GSH plays an important role in the biochemical defense system in the human body and has various physiological functions. Its main physiological function is to remove free radicals in the human body, and as an important antioxidant in the body, it protects the sulfhydryl groups in many molecules such as proteins and enzymes. In addition, GSH also has functions such as detoxification, liver protection, radiation resistance, immunity enhancement, and anti-allergy. The lack of GSH in the human body can cause many health problems, such as: skin damage, hair pigment loss, liver damage and so on. In view of the fact that GSH is so important to the human body, it is of gr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D491/107G01N21/64
CPCC07D491/107C09K11/06C09K2211/1022C09K2211/1033G01N21/6408
Inventor 包晓峰吴小磊舒海曹乾升史加新
Owner NANJING UNIV OF SCI & TECH
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