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Near-infrared fluorescent probe for identifying hydrogen sulfide as well as preparation method and application thereof

A fluorescent probe, near-infrared technology, used in chemical instruments and methods, preparations for in vivo experiments, fluorescence/phosphorescence, etc., can solve the problems of sensitivity and accuracy of fluorescence analysis, and achieve good biological tissue permeability, Highly selective, less toxic effect

Active Publication Date: 2019-06-04
SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] Although some fluorescent probes that can be used for the detection of intracellular hydrogen sulfide have been reported in the literature, most of the fluorescent probes emit in the ultraviolet-visible region (400-600nm), and many small molecules in biological systems are in the ultraviolet-visible region. There is often autofluorescence in the wavelength range, which will greatly affect the sensitivity and accuracy of fluorescence analysis

Method used

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  • Near-infrared fluorescent probe for identifying hydrogen sulfide as well as preparation method and application thereof
  • Near-infrared fluorescent probe for identifying hydrogen sulfide as well as preparation method and application thereof
  • Near-infrared fluorescent probe for identifying hydrogen sulfide as well as preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0049] This example is used to illustrate the preparation of the fluorescent probe of the present invention.

[0050] The reaction formula is as follows:

[0051]

[0052] The preparation steps are as follows:

[0053] 1) Preparation of REDCP: 2-(3,5,5-trimethylcyclohex-2-enyl)malononitrile (100mg, 0.54mmol) and 4-(piperazin-1-yl)benzaldehyde ( 102mg, 0.54mmol) was dissolved in absolute ethanol (15ml). Then, five drops of piperidine were added to the solution under the protection of argon. After heating to reflux for 5 hours, the mixture solution was cooled to room temperature, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography with dichloromethane / methanol (200:1) as eluent to give red solid REDCP (119 mg, 0.33 mmol) in 61% yield.

[0054] 2) Preparation of NIR-NP: under the protection of argon, 0.1mL N,N-diisopropyl-ethylamine (DIPEA) was added to 15ml of REDCP in anhydrous dichloromethane solution (9...

Embodiment 2

[0057] This example is used to illustrate that the fluorescence of NIR-NP varies with Na 2 Positive correlation change of S equivalent.

[0058] Different equivalents of Na 2 S was added to the probe NIR-NP solution and incubated at 37°C for 1 hour, excited with a 440nm laser, and its emission spectrum was recorded. Such as figure 2 (a) and figure 2 As shown in (b), in the absence of Na 2 In the case of S, almost no fluorescence is observed because the strong electron-pulling effect of NBD quenches the fluorescence. Added different concentrations of Na 2 After S, obvious fluorescence can be observed at 670nm, and the fluorescence intensity increases with Na 2 increases with the increase of S. figure 2 (a) and figure 2 (b) shows Na in the range of 0-100μM 2 Good linear relationship between S concentration and fluorescence intensity. Through calculation, the detection limit of this probe can be obtained as 0.03 μM, which is much lower than that of H in mammalian se...

Embodiment 3

[0060] This example is used to illustrate that NIR-NP and Na 2 The change of fluorescence intensity with time after S reaction.

[0061] Add 100 μM Na to 10 μM NIR-NP solution 2 S, The fluorescence intensity of the probe was recorded with a fluorometer as a function of time. Such as image 3 As shown, the fluorescence intensity increased significantly and reached a maximum within 15 minutes of incubation. This result indicates that the probe can rapidly react with hydrogen sulfide in a short time, thereby quantitatively measuring hydrogen sulfide and dynamically monitoring the real-time production of endogenous hydrogen sulfide.

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Abstract

The invention belongs to the field of organic micromolecule fluorescent probes, and relates to a near-infrared fluorescent probe for identifying hydrogen sulfide as well as a preparation method and application thereof; and the fluorescent probe has a structure as shown in a formula I, is a near-infrared probe, has good biological tissue permeability, high sensitivity, high selectivity and low cytotoxicity, can prevent interference from biological macromolecular background fluorescence, can be used for detecting endogenous hydrogen sulfide of living cells and has a wide application prospect.

Description

technical field [0001] The invention belongs to the field of small organic molecule fluorescent probes, and more specifically relates to a near-infrared fluorescent probe for identifying hydrogen sulfide and its preparation method and application. Background technique [0002] Hydrogen sulfide is a natural gas that smells like rotten eggs. After carbon monoxide and nitric oxide, hydrogen sulfide is the third gas molecule identified as having a signaling function. As an important signaling molecule, endogenous hydrogen sulfide plays an important role in many physiological and pathological processes, such as neuromodulation, anti-inflammation, angiogenesis, vasodilation, and atherosclerosis. Endogenous hydrogen sulfide can be produced through enzymatic reactions through cysteine ​​and its derivatives, or through non-enzymatic pathways during the metabolism of sulfur-containing compounds or polysulfide compounds in the body. At present, four enzymes have been reported to cata...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/12C09K11/06A61K49/00G01N21/64
Inventor 谭英张洁雯黄小婷谭春燕
Owner SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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