Small-molecule fluorescent probe, preparation method and application thereof

A fluorescent probe and small molecule technology, applied in the field of small molecule fluorescent probe and preparation, can solve the problems of insufficient application potential exploration, low water solubility, and high detection limit, and achieve good application prospects, simple synthesis methods, and convenient operation. Effect

Inactive Publication Date: 2021-07-23
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In recent years, many small-molecule fluorescent probes have been reported for the recognition of hypochlorous acid or its ions, but at present, such hypochlorous acid probes have the following problems: complex design and synthesis steps, sensitivity and / or selectivity Insufficient, low water solubility, high detection limit, insufficient exploration of application potential, etc.
These deficiencies limit their use and applications, thus the need to develop new HClO probes to address current challenges

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  • Small-molecule fluorescent probe, preparation method and application thereof
  • Small-molecule fluorescent probe, preparation method and application thereof
  • Small-molecule fluorescent probe, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Synthesis of Small Molecule Fluorescent Probes

[0033] The chemical formula of the synthetic small molecule fluorescent probe is as follows figure 1 Shown, wherein EtOH is ethanol, RT is room temperature.

[0034] The specific synthesis process is as follows: 7-(diethylamino)-2-oxo-2H-methylene-3-carbaldehyde (150 mg, 0.5 mmol) was dissolved in 15 mL ethanol solution, and furan was added at room temperature -2-Carbohydrazide (120mg, 0.5 mmol) was stirred, stirred at room temperature and reacted for 8h, and an orange solid was obtained from the reaction, which was washed and dried with ethanol; the above orange solid powder was dissolved in ethanol, then heated and stirred and filtered, and the filtrate was slowly volatilized for several days to obtain pure target product. Such as figure 2 , 3 As shown, the product can be determined to be the target small molecule fluorescent probe by means of mass spectrometry, NMR and spectroscopy.

Embodiment 2

[0035] Example 2: Ultraviolet and fluorescence spectra of small molecule fluorescent probes in response to hypochlorous acid

[0036] Prepare 0.5 mL small molecule fluorescent probe (10.0×10 -6 mol / L) of H 2 O (with 1% EtOH) solution. 0-50 µM hypochlorous acid solution was added dropwise to the probe solution, e.g. Figure 4 As shown in (A), after adding hypochlorous acid into the probe solution, the absorption band at 450 nm gradually decreases, and there is a new absorption peak at 200 nm to 300 nm, and the maximum absorption peak appears at 260 nm, Its absorbance intensity increases gradually with ion concentration.

[0037] In the fluorescence titration experiment, prepare 3 mL of small molecule probe (10.0×10 -6 mol / L) of H 2 O (containing 1% ethanol) solution. 0-50 µM hypochlorous acid solution was added dropwise to the probe solution, and the fluorescence value of the probe from 420 nm to 660 nm was measured with 365 nm as the excitation wavelength. The experime...

Embodiment 3

[0038] Example 3: Verification of the selectivity of small molecule fluorescent probes to hypochlorous acid

[0039] Prepare 5 mL molecular probe (10.0×10 -6 mol / L) of H 2O (containing 1% ethanol) solution. Various interference medium solutions were prepared by dissolving the corresponding salts in deionized water (O 2 - , Cl - , NO 2 - , AcO - , •OH, 1 o 2 , SO 4 2- , CO 3 2- ,S 2 o 3 2- , Cys, H 2 o 2 and GSH, 50.0×10 -6 mol / L). Subsequently, equal equivalents of hypochlorous acid solution and these interfering media were added to the probe solution, respectively. Detection is carried out by fluorescence spectrum, and the ratio of fluorescence emission wavelength (F 430 / F 518 )comparing. The results show( Figure 5 A), these interfering media have no obvious change in the fluorescence of the probe as hypochlorous acid, which belongs to the ROS series • OH, 1 o 2 , H 2 o 2 Also had a slight effect but still insignificant compared to hypochlorou...

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Abstract

The invention discloses a small-molecule fluorescent probe, a preparation method and application thereof. A connecting part in the small-molecule fluorescent probe is easily oxidized by hypochlorous acid to cause falling of a 2-thiophenecarboxylic hydrazide group, so that a coumarin derivative is generated, and meanwhile, the fluorescence of the probe is also converted from green to blue. Therefore, the hypochlorous acid or hypochlorite ions can be accurately and rapidly detected in an ultraviolet and fluorescence ratio mode, and the fluorescent probe can be used for detecting exogenous hypochlorous acid or hypochlorite ions in solutions, bacteria, living cells and zebra fishes. The synthesis method is simple and convenient to operate, does not need harsh conditions, and is very high in synthesis yield and purity. Therefore, the probe has a good application prospect in the aspect of hypochlorous acid or hypochlorite ion detection.

Description

technical field [0001] The invention belongs to the field of fluorescent imaging molecular probes, and in particular relates to a small molecular fluorescent probe, a preparation method and an application thereof. Background technique [0002] Fluorescence detection technology is a technology that uses spectroscopy to reflect the characteristics of the material structure itself. It is the most commonly used analytical method. Fluorescence imaging is also a simple and effective method for detecting various ions. However, this method has certain limitations in terms of sample requirements and working environment. In addition, the selectivity and sensitivity of most probes have certain limitations, and are severely interfered by other ions, resulting in large errors, so developing a probe with high selectivity and sensitivity is a technical challenge. [0003] Reactive oxygen species (ROS) consisting of hydroxyl radicals, singlet oxygen, nitric oxide, hydrogen peroxide, supero...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/12C09K11/06G01N21/64A61K49/00
CPCC07D409/12C09K11/06G01N21/643G01N21/6428A61K49/0039C09K2211/1088C09K2211/1092G01N2021/6417
Inventor 丁峰王居平元文浩林刻智周鹏
Owner WENZHOU MEDICAL UNIV
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