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Fluorescent probe with large Stokes shift as well as synthesis method and application of fluorescent probe

A technology of fluorescent probes and synthesis methods, applied in fluorescence/phosphorescence, chemical instruments and methods, organic chemistry, etc., to achieve the effects of good research value, simple operation, and convenient purification

Active Publication Date: 2019-07-19
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most probes have difficulty distinguishing Cys from Hcy, GSH, or other reactive sulfur species (RSS), and the emission wavelength of the probes is ultraviolet / short wavelength, usually with a small Stokes shift type (<100nm)

Method used

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  • Fluorescent probe with large Stokes shift as well as synthesis method and application of fluorescent probe
  • Fluorescent probe with large Stokes shift as well as synthesis method and application of fluorescent probe
  • Fluorescent probe with large Stokes shift as well as synthesis method and application of fluorescent probe

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preparation example Construction

[0057] The invention also discloses a method for synthesizing a fluorescent probe with a large Stokes shift, and the specific steps include:

[0058] (1) Dissolve 2-aminothiophenol, 5-methyl salicylaldehyde and iodine in methanol, stir and react at room temperature for 3-5 hours, and obtain compound 1 by suction filtration;

[0059] (2) Dissolving compound 1 and hexamethylenetetramine in trifluoroacetic acid, heating and refluxing at 105°C to 115°C for 22 to 24 hours, and adjusting the pH to neutral, precipitated solid, and filtered to obtain compound 2;

[0060] (3) Dissolve compound 2 in acetone, heat to 45°C-55°C, then slowly add alkali solution dropwise until the solution turns red, continue heating for 3-5h to obtain compound 3;

[0061] (4) Compound 3 was dissolved in CH containing triethylamine 2 Cl 2 , stirring at low temperature, while slowly adding acryloyl chloride to react, and moving the reaction solution to room temperature and stirring for 3 to 5 hours, then t...

Embodiment 1

[0068] Synthesis of fluorescent probes with large Stokes shifts:

[0069] (1) Synthesis of compound 1:

[0070] 2-Aminothiophenol (10.0mmol), 5-methylsalicylaldehyde (10.0mmol) and iodine (5.0mmol), stirred at room temperature, obtained compound 1 by suction filtration; the solvent of the reaction was methanol; the reaction The time is 4h.

[0071] (2) Synthesis of compound 2:

[0072] Dissolve 0.432 g (2.0 mmol) of 2-(2-hydroxyphenyl)-benzothiazole (HBT) and 0.840 g (6.0 mmol) of hexamethylenetetramine in 20 mL of TFA, and store the contents at 110 °C Heated to reflux and stirred for 24 hours, then stopped heating and allowed to cool to room temperature; the solution was neutralized with 1N NaOH, and the resulting precipitate was filtered and washed with water; finally on a silica gel column (CH 2 Cl 2 and MeOH 100:1, v / v) to give pure product compound 2.

[0073] (3) Synthesis of compound 3:

[0074] Dissolve 0.400g (1.5mmol) of compound 2 in 20mL of acetone, heat to 5...

Embodiment 2

[0078] Synthesis of fluorescent probes with large Stokes shifts:

[0079] The difference between this embodiment and Example 1 is that the reaction time of Step 1 in Example 1 is replaced with 3 hours, and the remaining reactants and experimental parameters refer to Example 1.

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Abstract

The invention discloses a fluorescent probe with large Stokes shift as well as a synthesis method and application of the fluorescent probe. According to the fluorescent probe with large Stokes shift disclosed by the invention, a typical ESIPT dye (HBT) is used as a fluorescent signal reporting group, and an acrylate group is used as an ESIPT blocking agent and a recognition unit to realize the detection of endogenous cysteine. When cysteine is added to a system, cracking of the acrylate part is rapidly and specifically realized, thereby causing the ESIPT process to recover and causing the probe to display an 'on' fluorescence detection procedure of cysteine, and strong fluorescence is shown at 595 nm. Recognition effects of the fluorescence probe with the large Stokes shift on various biological mercaptan and sulfides are studied through an ultraviolet-visible absorption spectrum method, a fluorescence spectrum method and the like, and results show that the fluorescence probe can efficiently recognize cysteine in a phosphate buffer solution and has very high response sensitivity to cysteine.

Description

technical field [0001] The invention belongs to the technical field of small molecule fluorescent probes, and relates to a method strategy for detecting cysteine. More specifically, it relates to a fluorescent probe with large Stokes shift, its synthesis method and application. Background technique [0002] Cysteine ​​(Cys) is an important amino acid containing a sulfhydryl group that is involved in cell growth, and the level of Cys is associated with many diseases. Therefore, it is important to develop fluorescent probes for Cys detection and imaging. So far, many fluorescent probes for Cys detection have been successfully constructed. However, most probes have difficulty distinguishing Cys from Hcy, GSH, or other reactive sulfur species (RSS), and the emission wavelength of the probes is ultraviolet / short wavelength, usually with a small Stokes shift type (<100nm). [0003] Therefore, the development of a highly selective and sensitive fluorescent probe with a large ...

Claims

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Application Information

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IPC IPC(8): C07D277/66C09K11/06G01N21/64
CPCC07D277/66C09K11/06G01N21/6428G01N21/6486C09K2211/1037
Inventor 张鹏肖玉哲张倩丁彩凤
Owner QINGDAO UNIV OF SCI & TECH
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