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A fluorescent probe for accurately detecting H2S2 in mitochondria through light regulation, its preparation method and application

A fluorescent probe, H2S2 technology, applied in the field of organic fluorescent probes, can solve the problems of unavoidable interference and lack of convincing research results, and achieve the effect of good cell permeability and good mitochondrial targeting.

Active Publication Date: 2018-11-13
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the study of mitochondria, fluorescent probes are mostly used. An ideal fluorescent probe is the dream of countless scientists. So far, many fluorescent probes have been reported, such as the detection of active oxygen clusters, active nitrogen clusters, metal ions, biological Fluorescent probes such as small molecules, but these fluorescent probes have a fatal shortcoming that they cannot avoid interference from the detected substances in the cytoplasm during the process of targeting mitochondria through the cytoplasm, resulting in a lack of convincing research results

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  • A fluorescent probe for accurately detecting H2S2 in mitochondria through light regulation, its preparation method and application
  • A fluorescent probe for accurately detecting H2S2 in mitochondria through light regulation, its preparation method and application
  • A fluorescent probe for accurately detecting H2S2 in mitochondria through light regulation, its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Precise detection of intramitochondrial H by photoregulation 2 S 2 The preparation method of the fluorescent probe is as follows:

[0028] (1) Dissolve 0.8g fluorescein in N,N-dimethylformamide DMF, then add 0.93g of K 2 CO 3 and 0.18ml of bromopropyne, wherein bromopropyne has 80% volume ratio in toluene, then stirred at 60°C for 1h, diluted the reaction mixture with water, then extracted and spin-dried, and purified by silica gel column chromatography to obtain fluorescent propyne monobromide. 1H NMR (300MHz, CDCl 3 ):δ10.14(s,1H),8.02(t,J=6Hz,1H), 7.82(t,J=7.5Hz,1H),7.75(t,J=7.5Hz,1H),7.30(d, J=6Hz, 1H), 7.01(d, J=3Hz, 1H), 6.74(m, 3H), 6.58(s, 1H), 4.89(d, J=1.5Hz, 2H), 3.62(d, J=1.5 Hz, 1H).

[0029] (2) Add 106 mg of N,N-dimethylformamide EDCI to 10 ml of dichloromethane in an ice bath, then add 193.9 mg of photoprotective group and 7 mg of 4-dimethylaminopyridine DMAP and stir for 10 min, 250 mg of fluorescein monobromopropyne was finally added and stirre...

Embodiment 2

[0033] Precise measurement of intramitochondrial H by light regulation 2 S 2 The preparation method of the fluorescent probe is as follows:

[0034] (1) Dissolve 1g of fluorescein in 4.5ml of N,N-dimethylformamide DMF solution, then add 1.16g of K 2 CO 3 And 0.244ml of bromopropyne, wherein bromopropyne has 80% volume ratio in toluene, then stirred at 60°C for 3h, diluted the reaction mixture with water, then extracted and spin-dried, and purified by silica gel column chromatography Obtain fluorescein monobromopropyne;

[0035] (2) Add 53.75mg of N,N-dimethylformamide EDCI to 5ml of dichloromethane in an ice bath, then add 114mg of photoprotective groups and 3.42mg of 4-dimethylaminopyridine DMAP and stir for 20min , 128 mg of fluorescein monobromopropyne was finally added and stirred for 26 hours, then filtered, rinsed with dichloromethane, the filtrate was selected to dryness, and then purified by silica gel column chromatography to obtain photoprotected fluorescein mono...

Embodiment 3

[0038] Precise measurement of intramitochondrial H by light regulation 2 S 2 The preparation method of the fluorescent probe is as follows:

[0039] (1) Dissolve 1.8g of fluorescein in 9ml of N,N-dimethylformamide DMF solution, then add 2.33g of K 2 CO 3 and 0.455ml of bromopropyne, wherein bromopropyne has 80% volume ratio in toluene, then stirred at 60°C for 4h, diluted the reaction mixture with water, then extracted and spin-dried, and purified by silica gel column chromatography to obtain fluorescent monobromopropyne;

[0040] (2) Add 107.5mg of N,N-dimethylformamide EDCI to 10ml of dichloromethane in an ice bath, then add 236mg of photoprotective group and 6.85mg of 4-dimethylaminopyridine DMAP and stir for 30min , 249.06 mg of fluorescein monobromopropyne was finally added and stirred for 20 hours, then filtered, rinsed with dichloromethane, the filtrate was selected to dryness, and then purified by silica gel column chromatography to obtain photoprotected fluorescei...

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Abstract

The invention relates to a fluorescent probe of precisely detecting H2S2 in mitochondria by means of light control and a preparation method and an application thereof and belongs to the field of organic fluorescent probes. H2S is the third human body gas signal molecular which is confirmed after NO and CO while, and under the action of ROS, H2S will be converted into H2S2, so that the H2S2 fluorescent probe is of quite important meaning. The structural formula of the Mito-H2S2 fluorescent probe is as shown in a formula (I). The fluorescent probe provided by the invention can precisely detect H2S2 in the mitochondria but avoids interference of H2S2 in the cytoplasms. In addition, the probe has the characteristics of relatively good mitochondria targeting property, chemical stability, biocompatibility, selectivity and the like. A laser confocal imaging experiment verifies that the probe has relatively good cell permeability, is free of toxic and side effects to cells and living bodies, can detect the active oxygen level of the subcellsular level and is further applied to researching neurodegenerative diseases and cancers.

Description

technical field [0001] The invention relates to a method for accurately detecting H in mitochondria through light regulation. 2 S 2 The fluorescent probe and its preparation method and application belong to the field of organic fluorescent probes. Background technique [0002] Hydrogen sulfide is the third confirmed human gas signal molecule after NO and CO, and plays a very important regulatory role in the process of nerve signal transduction. At the same time, hydrogen sulfide has also been found to have many important physiological functions in the cardiovascular system, such as regulating the relaxation of vascular smooth muscle, anti-oxidation, inhibiting inflammation, and reducing metabolic rate. Abnormal levels of hydrogen sulfide are also thought to be closely related to Alzheimer's disease, Down syndrome, diabetes and liver cirrhosis, among others. The research on the physiological and pathological functions of hydrogen sulfide has become a hot spot in chemistry ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6561C09K11/06G01N21/64
CPCC07F9/6561C09K11/06C09K2211/1059C09K2211/1088G01N21/6428G01N21/6458
Inventor 张承武李林韩林奇王刘林慈乔乔仇兴汉王彦滨黄维
Owner NANJING TECH UNIV
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