A mitochondrial-targeted nitrosyl hydrogen molecular fluorescent probe and its preparation method and application

A nitrosyl hydrogen and fluorescent probe technology, applied in the field of analytical chemistry, can solve problems such as DNA chain damage and body damage, and achieve the effects of good selectivity, easy synthesis, and strong resistance to other molecular interference.

Inactive Publication Date: 2018-02-13
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the abnormal content of HNO in the body may cause greater damage to the body. For example, the oxidation product of HNO has strong oxidation energy, which can damage the DNA chain in the cell.

Method used

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  • A mitochondrial-targeted nitrosyl hydrogen molecular fluorescent probe and its preparation method and application
  • A mitochondrial-targeted nitrosyl hydrogen molecular fluorescent probe and its preparation method and application
  • A mitochondrial-targeted nitrosyl hydrogen molecular fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthesis of target probe Mito-HN

[0039] 1) Synthesis of compound MHN-1:

[0040]

[0041] Compound 2′,4′-dihydroxy-2-phenonebenzoic acid (1.0g, 3.88mmol, 1eq) and m-hydroxyphenylpiperazine (758.3mg, 4.26mmol, 1.1eq) were dissolved in 20mL of trifluoroacetic acid, Heat to reflux at 90°C and react overnight. Use a TLC plate to detect the reaction. After the reaction is complete, spin dry the solvent trifluoroacetic acid under reduced pressure, dissolve it with 1ml ethyl acetate, and separate it with a silica gel column. The silica gel particle size is 200-300 mesh, and the eluent ratio is methanol / di Chloromethane=1:5. The yield was 81%.

[0042] 2) Synthesis of compound MHN-2:

[0043]

[0044] Compound MHN-2 (1.1g, 2.74mmol, 1eq), NaHCO 3(691mg, 8.22mmol, 3eq) was dissolved in 20mL of acetonitrile and reacted at room temperature for 10min, then added Fmoc-Cl (850mg, 3.29mmol, 1.2eq), under nitrogen protection, reacted at room temperature for 3h, detected t...

Embodiment 2

[0055] Changes of the fluorescence spectrum of the fluorescent probe Mito-HN with the increase of HNO addition

[0056] The Mito-HN fluorescent hydrogen nitrosyl probe prepared in Example 1 was dissolved in N,N-dimethylformamide (DMF) to prepare a 1 mmol / L stock solution. Take 30 μL from the stock solution and add it to a 5 mL centrifuge tube, dilute it with 2 mL of PBS (0.1 mol / L, pH=7.4), and then add different equivalents (0-10 eq) of AS salt (HNO donor) standard solution, Dilute it to 3mL with PBS buffer solution, and measure its fluorescence properties with 450nm as excitation light. Fluorescence spectra such as figure 2 shown. Depend on figure 2 It can be seen that the fluorescence at 545nm increases gradually with the increase of the amount of HNO added.

Embodiment 3

[0058] The selectivity of compound Mito-HN nitrosyl hydrogen fluorescent probe to different molecules or ions

[0059] Take 30 μL from the fluorescent probe stock solution in Example 2 and add them to 18 5mL centrifuge tubes respectively. After diluting with 2mL PBS, add equimolar amounts of competing molecular standard solutions to 16 centrifuge tubes respectively, one of which Do not add any ions, as a blank sample, and add an equimolar amount of HNO standard solution to the other, and detect the change of the fluorescence emission spectrum of the solution after 15 minutes, with 450nm as the excitation light, the results are as follows: image 3 and Figure 4 shown. Depend on image 3 and Figure 4 It can be found that other metal ions, reducing compounds, oxidizing compounds, etc. have almost no effect on the fluorescence of compound Mito-HN at 545nm, but the addition of nitrosyl hydrogen solution can significantly enhance the fluorescence of compound Mito-HN at 545nm. ...

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Abstract

The invention discloses a nitrosyl hydrogen molecular fluorescent probe for mitochondria targeting and a preparation method and application thereof, and belongs to the technical field of analysis chemistry. The probe molecule has the structure formula (I) (please see the formula in the description) and is a first-synthesized fluorescent probe for detecting HNO molecules in cell mitochondria. The synthesis method of the probe is easy, high in yield, simple in post-treatment process. The selective rapid detection of the HNO molecule probe is achieved, selectivity is high, and the capacity of resisting interference of other molecules is high. The probe is a simple, rapid and sensitive HNO molecule specificity detection agent and has wide application prospects in the field of biomolecular detection.

Description

technical field [0001] The invention relates to a mitochondrial-targeted nitrosyl hydrogen molecular fluorescent probe and a preparation method and application thereof, belonging to the technical field of analytical chemistry. Background technique [0002] Studies have shown that hydrogen nitrosyl (HNO) plays an important role in many physiological processes in organisms. For example, HNO can enhance the contraction of heart cells, increase the expansion of blood vessels and reduce the aggregation of platelets in muscle tissue. In nonvascular cells, HNO is known to prevent lipid peroxidation, thereby promoting the expression of heme oxidase. In addition, studies have shown that HNO can trigger the voltage-dependent K + Channels that promote relaxation of arteries. Through animal experiments, it was found that HNO can not only enhance the stretching energy of myocardial myofilaments in mice, but also increase Ca 2+ Absorption in mouse myocardium. However, the abnormal co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07F9/38G01N21/64
CPCC07F9/3834C09K11/06C09K2211/1007C09K2211/1044C09K2211/1088C09K2211/1096G01N21/6428G01N21/6447
Inventor 林伟英任明光邓贝贝周凯
Owner UNIV OF JINAN
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