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Fluorescent probe for detecting histidine, precursor thereof and preparation methods of fluorescent probe and precursor

A technology of fluorescent probes and precursors, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve the problems of limiting the wide application of probes, short fluorescence emission wavelengths, and difficult probe synthesis, and achieve good water solubility. high sensitivity, low anti-interference effect

Inactive Publication Date: 2012-06-27
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these probes are difficult to synthesize, or due to the disadvantages of low quantum yield and short fluorescence emission wavelength, which limit the wide application of these probes.

Method used

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  • Fluorescent probe for detecting histidine, precursor thereof and preparation methods of fluorescent probe and precursor
  • Fluorescent probe for detecting histidine, precursor thereof and preparation methods of fluorescent probe and precursor
  • Fluorescent probe for detecting histidine, precursor thereof and preparation methods of fluorescent probe and precursor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The preparation of compound shown in formula Ia

[0033] (1) Synthesis of Compound A1

[0034] Dissolve 0.5 g (1.6 mmol) of 4-bromo-5-nitro-1,8-naphthalic anhydride in 20 ml of ethanol, and stir well. Add 0.096g n-butylamine (1.6mmol), heat to reflux for three hours, track with TCL spot plate, until the point of raw material disappears or no longer diminishes, it is the end of the reaction. Cool, filter, and recrystallize with ethanol to obtain a brown solid. Melting point: 175.8-176.2°C. Yield: 77.8%.

[0035] 1 H NMR (400MHz, CDCl 3 , 20°C): δ8.71(d, J=7.6Hz, 1H), 8.52(d, J=8.0Hz, 1H), 8.22(d, J=8.0Hz, 1H), 7.94(d, J=8.0 Hz, 1H), 4.18(t, J=7.6Hz, 2H), 1.76-1.68(m, 2H), 1.50-1.41(m, 2H), 0.99(t, J=7.2Hz, 3H).

[0036] 13 C NMR (100MHz, CDCl 3 , 20°C): δ162.79, 162.02, 151.25, 135.96, 132.32, 131.20, 130.52, 125.77, 124.07, 123.54, 122.48, 121.19, 40.74, 30.02, 20.31, 13.79.

[0037] (2) Synthesis of compound A2

[0038] 1.0 g (2.6 mmol) of compound A1 was di...

Embodiment 2

[0049] The preparation of compound shown in formula IIb

[0050] (1) Synthesis of compound B1

[0051] In a 100 mL round bottom flask, 7-hydroxycoumarin (3.1 g, 19.1 mmol) was added to 50 mL of dichloromethane to form a suspension, then 2 mL of acetic anhydride and a drop of pyridine were added. The above reaction solution was stirred overnight at room temperature to obtain a light yellow clear solution. The solvent dichloromethane was spin-dried under reduced pressure to obtain a light yellow crude product solid. It was then added to 100 mL of water, extracted with ethyl acetate, the organic layer was taken, the water layer was discarded, dried over anhydrous sodium sulfate, and the ethyl acetate was removed by a rotary evaporator to obtain a light yellow solid. It was separated by column chromatography (petroleum ether:ethyl acetate=2:1, (v / v)) to obtain 3.8 g (yield 97%) of a white solid.

[0052] 1 H NMR (400MHz, CDCl 3 ): δ7.71(d, 1H, J=4.8Hz), 7.51(d, J=4.2Hz, 1H), ...

Embodiment 3

[0065] The UV and Fluorescence Spectrum Properties of Compounds Ia and IIb

[0066] Compound Ia and Compound IIb are configured into 10 -3 mol / L DMSO stock solution, and then diluted 10 with the corresponding buffer solution -5 mol / L concentration of the test solution, and then add different concentrations of metal ions to test the ultraviolet absorption and fluorescence emission of the metal complex. like figure 1 , figure 2 As shown, compound I complex metal Cu 2+ After that, the maximum ultraviolet absorption is at 460nm, and the maximum fluorescence emission is 472nm; Compound II is complexed with metal Ni 2+ Finally, the maximum UV absorption is at 350nm, and the maximum fluorescence emission is at 454nm.

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Abstract

The invention relates to a fluorescent probe for detecting histidine, a precursor thereof and preparation methods of the fluorescent probe and the precursor. The fluorescent probe which can be used for detecting histidine is obtained by preparing precursors of two fluorescent probes in a way of taking naphthalimide or 7-hydroxy coumarin as a fluorophore and complexing with a metal respectively. After histidine is combined, the fluorescent light of a fluorescent probe Ia at a position of 476 nanometers is enhanced slightly, and the fluorescent light of the fluorescent probe Ia at a position of 537 nanometers is enhanced remarkably; and the fluorescent light of a fluorescent probe IIb at a position of 454 nanometers is enhanced remarkably. Moreover, the fluorescent probe provided by the invention has the advantages that: (1) the fluorescent probe has high water solubility, and can be suitable for detecting histidine of a biological system; (2) the fluorescent probe has high stability, can be stored for a long time, and is suitable for various neutral, weakly-acid and weakly-alkaline environment systems, and the like; and (3) the fluorescent probe has the advantages of very high sensitivity, interference resistance (very small interference with other amino acid actions), and the like.

Description

technical field [0001] The invention relates to a fluorescent probe for detecting histidine, its precursor and their preparation method. Background technique [0002] Histidine is one of the basic 20 amino acids. For infants and children, histidine is an essential amino acid for the human body. After many years of development, the human body can synthesize it by itself. Histidine is crucial in the physiological activities of the human body. The imidazole ring on the histidine branch is the binding site of many metalloproteins, and it is also the catalytic center of some specified enzymes [Chen, G.N.; Wu, X.P.; Duan, J.P.; Chen, H.Q.Talanta 1999(49): 319- 330]. Histidine can maintain the normal metabolism of the organism and protect the nerve cells that transmit information from the brain to all parts of the body. However, the content of histidine in the body must be maintained within a certain range, and abnormal levels of histidine are usually a precursor to some disease...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07D405/12C09K11/06G01N21/64
CPCC07D401/12C07D405/12C09K11/06C09K2211/1029C09K2211/1044C09K2211/1088G01N21/64
Inventor 徐玉芳钱旭红张沈裔杨泱泱朱维平
Owner EAST CHINA UNIV OF SCI & TECH
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