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Mitochondria-targeted peroxynitrite/bisulfite double-response fluorescent probe

A technology of peroxynitrite and bisulfite, applied in fluorescence/phosphorescence, material analysis by optical means, luminescent materials, etc., can solve the problem of inability to detect two molecules at the same time, lack of biological targeting of probes, etc. question

Active Publication Date: 2021-12-17
FIRST HOSPITAL OF SHANXI MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In view of the lack of biological targeting of most probes and the inability to detect two molecules at the same time, it is impossible to deeply study the relationship between two or more small molecules in the body and a specific disease and study its pathogenic mechanism. The invention provides a mitochondria-targeted peroxynitrite / bisulfite dual-response fluorescent probe

Method used

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  • Mitochondria-targeted peroxynitrite/bisulfite double-response fluorescent probe
  • Mitochondria-targeted peroxynitrite/bisulfite double-response fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Mitochondrial targeted peroxy-nitrate / sulfite dual response fluorescent probe

[0034] like figure 1 The synthesis road map shows that the compound Ni synthesis: Under nitrogen protection, aminophenols (5 g, 30 mmol), NaH (0.73 g, 30 mmol) were dissolved in 50 ml DMF, and stirred at room temperature for 10 min to give a reaction Liquid; then IR-780 (10.0 g, 15 mmol) was dissolved in 100 ml DMF to give a secondary reaction solution, and the solution was slowly added dropwise to the primary reaction solution, 50 ° C for 5 hours. The TLC showed completely, the solvent was dried, and the crude product was separated from the column chromatography (dichloromethane: methanol = 100: 1 to 10: 1) to give 3.9 g of red solid.

[0035] like figure 2 Probes of this invention 1 H NMR spectrum, 1 H NMR (400MHz, CDCL 3 )δ 1 HNMR (400MHz, CDCL 3 Δ8.49 (D, J = 14.5 Hz, 1H), 7.55 (S, 1H), 7.49-7.38 (m, 3H), 7.29 (S, 1H), 7.20 (D, J = 7.6 Hz, 1H), 6.80 (D, J = 8.8 Hz, 1H), 6.50 (S, 1H), 6.15 ...

Embodiment 2

[0038] Fluorescence for different concentrations of HSO 3 - And onoo - Identification

[0039] The fluorescent probe prepared in Example 1 was formulated into a DMSO mother liquor, which added different equivalents of HSO, respectively. 3 - And onoo - The solution was diluted with a phosphate buffer solution (pH = 7.4) to the concentration of 20 μm to be tested, and the fluorescence spectrum measurement was performed. like Figure 5 6. As shown, as the ion concentration to be tested, the probe exhibits a variation of fluorescence.

Embodiment 3

[0041] Fluorescence selection of different ions or molecules

[0042] The fluorescent probes prepared in Example 1 were formulated into a DMSO mother liquor, and 100 equivalents of ACO were added separately. - , F - , CL - BR - I - , CLO - , CN - , CO 3 2- , HCO 3 - HS - NO 3 - , PO 4 3- S 2 O 3 2- SO 4 2- SO 3 2- And 20 equivalents of HSO 3 - After diluting with a phosphate buffer solution (pH = 7.4) to the concentration of 20 μm to be tested, after 30 min at 37 ° C, the fluorescence spectrum was determined (λ) ex = 450 nm); According to its fluorescence intensity, the effect of different ions on fluorescence intensity of fluorescence probes is evaluated. Figure 7 a shown. Where 1-17 is 1.BLANK, 2.aco, respectively. - , 3.F - , 4.cl - , 5.br - , 6.i - , 7.Clo - , 8.cn - , 9.co 3 2- , 10.hco 3 - 11.HS - 12.no 3 - , 13.po 4 3- , 14.s 2 O 3 2- , 15.so 4 2- 16.so 3 2- 17.hso 3 - . This means that the fluorescent probe of the present invention is only HSO at 588 nm. 3 ...

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Abstract

The invention discloses a mitochondria-targeted peroxynitrite / bisulfite double-response fluorescent probe, and belongs to the technical field of chemical biological materials. The invention aims to solve the problems that most probes lack biological targeting and cannot detect two molecules at the same time, so that the relationship between two or more micromolecules and a specific disease in a living body cannot be deeply studied and the pathogenesis of the micromolecules cannot be studied. The peroxynitrite / bisulfite double-response fluorescent probe, disclosed by the invention, can target mitochondria; the preparation method of the fluorescent probe comprises the following steps: dissolving m-diethylaminophenol and sodium hydride in N, N-dimethylformamide under the protection of nitrogen, and stirring at room temperature; then adding a near-infrared dye IR-780 into the reaction liquid, and heating to react; and concentrating the reaction liquid, and carrying out column chromatography separation to obtain a target compound NI, namely the peroxynitrite / bisulfite double-response fluorescent probe.

Description

Technical field [0001] The present invention belongs to the field of chemical biomaterials, and specifically, the hydroximetic acid / sulfite root dual response fluorescence probe targeted by mitochondria. Background technique [0002] Peroxidate (onoo) - ) Is from superior oxygen free radicals (O 2 · - High-reaction active oxygen / nitrogen molecules produced with nitric oxide (NO) diffusion, mainly in mitochondria, is a key cell signal molecule during physiological and pathological processes. Bast ONOO - It has strong oxidation and nucleophilicity, playing the role of regulating physiological activities in the biology, for example, by nitrate tyrosine residues involved in cell signal transduction process; can participate in certain reactions with biomolecules such as proteins, lipids and nucleic acids. It causes mitochondrial dysfunction and even ultimately induces apoptosis. Also, ONOO - It is closely related to the pathogenesis of cardiovascular disease, neurodegenerative dis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06C09K11/06G01N21/64
CPCC07D405/06C09K11/06G01N21/6428C09K2211/1029C09K2211/1088
Inventor 马素芳李思进武志芳余强耿佳美
Owner FIRST HOSPITAL OF SHANXI MEDICAL UNIV
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