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Difunctional fluorescent probe, preparation method and application

A fluorescent probe and dual-function technology, which is applied in the field of fluorescent probe preparation, can solve the problems of large effect influence, long response time, poor water solubility of the probe, etc., and achieve simple preparation process, good selectivity and specificity Sexuality and ease of large-scale production

Active Publication Date: 2017-04-26
NANJING UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few fluorescent probes that can locate intracellular mitochondria with high accuracy, and many of them have poor water solubility, low sensitivity, long response time, and changes in pH have a greater impact on the detection effect; High toxicity and poor cell membrane permeability, these defects greatly affect the application of the probe

Method used

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  • Difunctional fluorescent probe, preparation method and application
  • Difunctional fluorescent probe, preparation method and application
  • Difunctional fluorescent probe, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 Preparation of Fluorescent Probes for HClO Detection and Mitochondrial Localization

[0031] Dissolve 269mg of 2-(5-methyl-4-formyl-2-hydroxyphenyl)benzothiazole and 235mg of 1,4-lutidine iodide in 60ml of ethanol solution, then piperidine 1.0mMo l Add dropwise to the above solution; under the condition of oil bath, vigorously stir the reaction overnight; Filter, vacuum-dry to obtain 393mg of tan solid, be the fluorescent probe pure product of HClO detection and mitochondria localization ( 1 H-NMR chart and high-resolution mass spectrogram see Figure 7 , Figure 8 ). The measured molecular weight of the obtained pure fluorescent probe was 486.37.

[0032] Present embodiment process route:

[0033]

Embodiment 2

[0034] Example 2 Spectral properties of HClO detection and mitochondrial localized fluorescent probes reacting with various ions

[0035] Weigh 4.9 mg of fluorescent probes for HClO detection and mitochondrial localization prepared in Example 1, and prepare 10 mL of CH with a concentration of 1 mM 3 CN solution, as the mother liquor.

[0036] Fluorescence spectrum test: Add 30 μL of the above mother solution into a certain amount of 10mM HEPES buffer solution (pH 7.4), and then add various ions: H 2 o 2 ,NO, . o 2 - ,ONOO - ,ROO . , 1 o 2 , . OH, ClO - , so that the final concentration of ions is 500 μM, and the final concentration of fluorescent probes is 10 μM. The fluorescence emission spectrum was tested immediately under the excitation wavelength of 398nm. The slit width for excitation and emission is 5 / 10nm. Income I 460nm / I 615nm The histogram of figure 1 shown. The solution prepared above was irradiated with a 365nm ultraviolet lamp, and the fluoresce...

Embodiment 3

[0040] Example 3 HClO Detection and Mitochondrial Localization Fluorescent Probes and ClO -Spectral properties of reaction products

[0041] 30 μ L of the mother solution in Example 2 was added to a certain amount of 10 mM HEPES buffer solution (pH 7.4), and then different equivalents of ClO were added - , so that the final concentration of the fluorescent probe is 10 μM, and the final concentration of gold ions is 0 μM, 0.1 mM, 0.2 mM, 0.3 mM, 0.4 mM, 0.5 mM, 0.6 mM, 0.7 mM, 0.8 mM, 0.9 mM, 1.0 mM, respectively. Immediately after the addition of ions, their fluorescence emission spectra were measured. The excitation wavelength is 398nm when measuring the fluorescence emission spectrum; the slit width of excitation and emission is 5 / 10nm. The resulting fluorescence intensity I 460nm / I 615nm Incremental graph see image 3 ; with I 460nm / I 615nm The data to make the working curve, the results are shown in Figure 4 .

[0042] The experimental results show that after t...

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Abstract

The invention discloses a difunctional fluorescent probe and provides a preparation method and application thereof. The fluorescent probe can detect HOCl in a high-selectivity and high-sensitivity manner and can locate mitochondria in cells. The difunctional fluorescent probe has double functions of hypochloric acid detecting and mitochondria locating in cells and has a structure shown as a formula 1, wherein R is H, CH3 or T-Bu, and the probe is a derivative of 2-(5-alkyl-4-formyl-2-hydroxy phenyl) benzothiazole.

Description

technical field [0001] The present invention relates to a fluorescent probe, its preparation method and application, more specifically to a dual-functional fluorescent probe, its preparation method and its application. Background technique [0002] HOCl / OCl- is a strong oxidizing agent, which makes it often play an important role in daily life as a bleach and disinfectant. In organisms, HOCl / OCl- is an important member of reactive oxygen species (ROS), which plays an extremely important role in the process of immunity against microbial infection and inflammation. In organisms, H2O2 and Cl- generate OCl- under the catalysis of myeloperoxidase (MPO), which is the main source of endogenous OCl-. The research results show that when the intracellular OCl-concentration level cannot be maintained within the normal physiological range, it will lead to various diseases of the organism, such as arthritis, rheumatoid arthritis, atherosclerosis and tumors, etc. . It can be seen that ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/10C09K11/06G01N21/64
CPCG01N21/6428G01N21/6486C09K11/06C07D417/10C09K2211/1037C09K2211/1029
Inventor 陈小强陈亚辉王芳吕静强健章智洁
Owner NANJING UNIV OF TECH
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