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Preparation method and applications of enhanced type fluorescent probe for detecting hydrogen sulfide

A fluorescent probe and hydrogen sulfide technology, applied in the field of fluorescent probes, can solve the problems of inability to detect hydrogen sulfide and have no mitochondrial localization function, and achieve the effects of good optical stability, no toxic side effects, and high selectivity.

Inactive Publication Date: 2015-04-01
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are many kinds of fluorescent probes for detecting hydrogen sulfide, but most of them do not have the function of mitochondrial localization, let alone detect hydrogen sulfide produced in mitochondria

Method used

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  • Preparation method and applications of enhanced type fluorescent probe for detecting hydrogen sulfide
  • Preparation method and applications of enhanced type fluorescent probe for detecting hydrogen sulfide
  • Preparation method and applications of enhanced type fluorescent probe for detecting hydrogen sulfide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Implementation 1 A method for preparing an enhanced fluorescent probe for detecting hydrogen sulfide

[0024] The preparation reaction formula is as follows:

[0025]

[0026] Among them: Nile Red (9-(dimethylamino)-2-hydroxy-5H-Benzo[a]phenoxazin-5-one) is commercially available in the United States and can also be synthesized.

[0027] Nile red (0.0183g, 0.06mmol), 2,4-dinitrofluorobenzene (0.0135g, 0.072mmol) and K 2 CO 3 (0.0099g, 0.072mmol) was dissolved in 8mL dimethylformamide (DMF), heated to 75°C, and refluxed for 3h. The reaction solution was poured into 50 mL of water, extracted with dichloromethane (50 mL×3), the organic phase was collected, dried over anhydrous magnesium sulfate, and purified by silica gel column chromatography (eluent CH 2 Cl 2 :CH 3 OH=40:1; SiO 2 300-400 mesh), to obtain the purple-red target product NRS fluorescent probe, H-NMR: (300MHz, DMSO-d6) δ8.97 (d, J=2.7Hz, 1H), 8.52 (dd, J=9.3, 2.7 Hz, 1.6Hz, 1H), 8.27(d, J=9.0Hz, 1H)...

Embodiment 2

[0028] Example 2 An enhanced fluorescent probe for detecting hydrogen sulfide for real-time detection of hydrogen sulfide in water

[0029] The NRS fluorescent probe prepared in Example 1 was dissolved in an aqueous solution of dimethyl sulfoxide, and the preparation concentration was 5×10 -6 NRS dimethyl sulfoxide solution of M, in which dimethyl sulfoxide DMSO and H 2 The volume ratio of O is 8:2, and the molar equivalent of Na is 3.2 times that of the NRS fluorescent probe to the NRS dimethyl sulfoxide solution successively. 2 S, after accumulation, it is 3.2 times, 6.4 times, 9.6 times, 12.8 times, 16 times... 51.2 times, 54.4 times Na 2 S, it can be seen that the color of the solution increases with the Na 2 The increase in S concentration changes from purple to red. Each solution was tested by UV spectrophotometry and fluorescence spectrophotometry, and the NRS fluorescent probes were plotted against different concentrations of Na 2 The absorption spectrum of S aqueo...

Embodiment 3

[0033] Example 3 An enhanced fluorescent probe for detecting hydrogen sulfide is used for real-time detection of hydrogen sulfide in the mitochondria of living cells

[0034] In the petri dish that contains live cell is Hela cell line, add concentration in embodiment 2 and be 5 * 10 -5 M NRS dimethyl sulfoxide solution, mixed evenly with cell culture medium, stained for 5 minutes, washed three times with phosphate buffer solution of pH = 7.4, added 50 times molar equivalent of sodium sulfide aqueous solution, and finally placed the culture dish Observed under a confocal microscope. The experimental results found that the mitochondria of Hela cells stained with NRS showed obvious fluorescence, such as Figure 6 Shown: (1) Rh123 staining, which can be localized in mitochondria. (2) is NRS staining, which coincides with Rh123, indicating that NRS can also be located in mitochondria. (3) is the overlay of (1) and (2). The experimental results show that NRS can enter cells and ...

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Abstract

The invention provides an enhanced type fluorescent probe for detecting hydrogen sulfide. The fluorescent probe is an NRS fluorescent probe, the structural general formula of the NRS fluorescent probe is shown as (I), the preparation method comprises the following steps: adding nile red, 2,4-dinitrofluorobenzene and potassium carbonate into dimethylformamide, heating to 70-80DEG C, performing reflux reaction for 3 hours, extracting the reaction liquor by dichloromethane and collecting an organic phase, drying the organic phase with anhydrous magnesium sulfate, and purifying through silica column chromatography to obtain a target product. The probe has a mitochondrial location function, can perform real-time and on-site online detection to mitochondria, and can help us to further master the physiological function of the hydrogen sulfide and promote the understanding of physiological action of H2S, and provide a visible detection tool for research and development of novel cardiovascular drugs.

Description

technical field [0001] The invention relates to a fluorescent probe for detecting hydrogen sulfide, in particular to an enhanced fluorescent probe for detecting hydrogen sulfide, a preparation method and application in mitochondria. Background technique [0002] Hydrogen sulfide (H 2 S) is a gas with a pungent odor, and it is the third small gas molecule with information transmission function after nitric oxide (NO) and carbon monoxide (CO). The hydrogen sulfide in the environment mainly comes from the release of hydrogen sulfide in the process of industrial production, water treatment and livestock breeding. Hydrogen sulfide plays an important role in the physiological processes of many organisms, such as the regulation of neurotransmission and the inhibition of insulin signaling. Abnormal levels of hydrogen sulfide may also be closely related to diseases such as Alzheimer's disease, Down syndrome, diabetes and liver cirrhosis. The research on the physiological and patho...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D265/38G01N21/64
Inventor 于海波李红玲方沛菊吕春娇宋有涛
Owner LIAONING UNIVERSITY
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