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A mitochondria-targeted fluorescent probe and its preparation method and application

A fluorescent probe and fluorescent molecular probe technology, applied in the field of light analysis and detection, can solve the problems of high cytotoxicity, weak anti-photobleaching ability, unsuitable for long-term mitochondrial imaging, etc., and achieve low cytotoxicity and anti-photobleaching ability. Strong, low-impact effects

Inactive Publication Date: 2019-01-29
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Now commonly used mitochondrial probes include Rhodamine 123, JC-1, Mitotracker series, etc. Although they have been used as commercial probes for mitochondrial imaging, they still have high cytotoxicity, weak anti-photobleaching ability, and are not suitable for long-term mitochondrial imaging. Therefore, it is necessary to develop a new mitochondrial fluorescent probe for mitochondrial imaging in living cells

Method used

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  • A mitochondria-targeted fluorescent probe and its preparation method and application
  • A mitochondria-targeted fluorescent probe and its preparation method and application
  • A mitochondria-targeted fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Preparation of fluorescent organic molecule (TEA-BODIPY) with mitochondrial targeting function

[0033] Dissolve p-hydroxybenzaldehyde (1.22g, 10mmol) and 1,4-dibromobutane (4.30g, 20mmol) in 20mL of anhydrous N,N-dimethylformamide (DMF), add anhydrous potassium carbonate (K 2 CO 3 ) (2.07g, 15mmol) was used as a base, reacted at room temperature to obtain a crude product, and passed through a chromatographic column to obtain compound 1. The eluent was n-hexane-acetone mixture of n-hexane / acetone (v / v)=8 / 1 , the structural formula of compound 1 is

[0034] Compound 1 (0.512g, 2mmol) and 2,4-dimethylpyrrole (0.380g, 4mmol) were dissolved in 200mL of dry dichloromethane, under the protection of nitrogen, a small amount of trifluoroacetic acid (TFA) was used as Catalyst, after stirring at room temperature for 12 hours, add 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (2.27g, 20mmol), then continue stirring at room temperature for 2 hours, stirring Add 5...

Embodiment 2

[0036] Example 2: Absorption and emission spectrum tests of mitochondrial targeting fluorescent probe TEA-BODIPY in different polar solutions

[0037] The spectrum test concentration that the present invention adopts is 10 μ M, and the solvent of test is aqueous solution and acetonitrile solution, and the absorption and emission spectra of TEA-BODIPY in different solvents are as follows: figure 2 and image 3 shown. The polarity of the solvent has little change on the absorption and emission spectra of the probe, and its Stokes shift has almost no change. It can be seen that the polarity of the solvent has little influence on the probe TEA-BODIPY.

Embodiment 3

[0038] Example 3: Test of fluorescence intensity of mitochondrial targeting fluorescent probe TEA-BODIPY under different pH conditions

[0039] The spectral test concentration that the present invention adopts is 10 μ M, and the test of the fluorescence intensity of TEA-BODIPY under pH condition is as follows Figure 4 shown. The pH has little effect on the fluorescence intensity of the probe, indicating that the probe can be used normally under the condition of physiological pH of the cell.

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Abstract

The invention discloses a mitochondria target fluorescence probe, as well as a preparation method and application thereof. The probe has a structure as shown in formula (I). The mitochondria target fluorescence probe can overcome the defects of the traditional commodity probe and has the advantages of high fluorescence quantum yield, excellent water solubility, less influences of environment property and acid-base property on the probe, good imaging effect of mitochondria, low toxicity, high photo-bleaching resistance, and the like, so that the mitochondria target fluorescence probe has excellent application prospects in the fields of long-time living cell mitochondria imaging and bio-labeling.

Description

technical field [0001] The invention belongs to the technical field of optical analysis and detection, and in particular relates to a mitochondria-targeted fluorescent probe and a preparation method and application thereof. Background technique [0002] Mitochondria are important organelles in cells and are the energy factories of cells. In addition, mitochondria have many important functions in cells, such as controlling cell metabolism, calcium ion regulation, and cell apoptosis pathway control. Mitochondria dysfunction It can lead to a variety of diseases, such as Parkinson's disease, Alzheimer's disease, etc. Therefore, mitochondrial imaging is of great significance for the diagnosis and treatment of subcellular levels. [0003] Now commonly used mitochondrial probes include rhodamine 123, JC-1, Mitotracker series, etc. Although they have been used as commercial probes for mitochondrial imaging, they still have high cytotoxicity, weak anti-photobleaching ability, and are...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1007C09K2211/1096G01N21/6486
Inventor 刘义高涛蒋风雷何欢黄蓉郑脉
Owner WUHAN UNIV