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H2S near-infrared fluorescent molecular probe as well as preparation method and application thereof

A fluorescent molecular probe and near-infrared technology, applied in fluorescence/phosphorescence, chemical instruments and methods, and material analysis through optical means, can solve problems such as fluorescence interference, achieve short response time, low cytotoxicity, and reduce interference Effect

Active Publication Date: 2020-12-18
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditional detection H 2 Most of the fluorescent probes of S are excited by visible light. 2 The fluorescence generated after the S response is easily interfered by the autofluorescence of the organism

Method used

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  • H2S near-infrared fluorescent molecular probe as well as preparation method and application thereof
  • H2S near-infrared fluorescent molecular probe as well as preparation method and application thereof
  • H2S near-infrared fluorescent molecular probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Preparation of near-infrared fluorescent probes for detecting hydrogen sulfide:

[0041] Compound 1 (1mmol) was added to a round-bottomed flask, N,N-dimethylformamide (12mL) was slowly added under nitrogen protection, stirred to dissolve completely, triethylamine (3mmol) was added under nitrogen protection, Continue to stir for 10 min, slowly add 3,5-dinitrobromobenzene (3 mmol) under nitrogen protection, and stir to dissolve completely. Put the above system in an oil bath, stir and heat to 85°C, react for 8 hours, wait until the solution turns dark blue, cool the system, pour the reaction solution in the bottle into a separatory funnel, add dichloromethane and distilled water, shake fully, and let stand Separating funnel, after the solution in the separating funnel is separated into layers, remove the lower organic layer. The above operation was repeated three times, and the organic layers were combined. The resulting solution was spin-dried to obtain a dark blue sol...

Embodiment 2

[0044] Near-infrared fluorescent probes and H 2 S in vitro response UV and fluorescence response experiments:

[0045] Weigh 6.12 mg (10 μmol) of the probe (NRh-DNBR) prepared in Example 1 and dissolve it in 1 mL DMSO to prepare a 10 mM probe stock solution. Weigh 5.6mg NaHS and dissolve it in 1mL water to make 100mM NaHS mother solution. 3 μL was drawn from the 10 mM probe mother solution and added to a cuvette filled with 3 mL of PBS buffer solution (pH=7.4), at which time the probe concentration was 10 μM. In the cuvette, add NaHS (final concentration 0-200μM) for ultraviolet and fluorescence response experiments (excitation light wavelength is 680nm), and the obtained data are processed by origin software. figure 2 , as shown in the figure, the UV absorption maximum of the probe before adding NaHS is at 680nm, and the fluorescence emission at 732nm is very low. After NaHS was added dropwise, the ultraviolet peak at 680nm decreased, the ultraviolet absorption peak at 71...

Embodiment 3

[0048] Optional experiment:

[0049] The NRh-DNBR probe (1 mM) and substrate (100 mM) prepared in Example 1 were prepared in DMSO. 30 μL was taken from each 100 mM substrate solution, respectively added to 12 centrifuge tubes containing 2940 μL of PBS buffer (pH=7.4) and mixed. Then 30 μL was taken from the 1 mM probe solution and added to each substrate solution respectively. The substrate to be tested is NaNO 2 , NaHCO 3 、H 2 o 2 , Cys, Hcy, GSH, Vc, Va, Na 2 SO 4 、Na 2 SO 3 、Na 2 S 2 o 3 , NaHS. Fluorescence emission spectra were measured with a four-color dish. The result is as image 3 As shown, only the NaHS group showed a strong fluorescent signal, that is, the fluorescent probe of the present invention was paired with H 2 S has good selectivity.

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Abstract

The invention discloses an H2S near-infrared fluorescent molecular probe as well as a preparation method and application thereof. The structural formula of the fluorescent probe is shown in the specification. The near-infrared fluorescence molecular probe for hydrogen sulfide is high in selectivity, high in sensitivity and good in response effect, can avoid biological autofluorescence interferencedue to the near-infrared absorption and fluorescence emission characteristics, and can be well applied to living cell imaging and the like. In addition, the preparation process is simple, the cost islow, the yield is high, the application prospect is wide, and large-scale production and application can be achieved.

Description

technical field [0001] The invention belongs to the technical field of fluorescent molecular probes, in particular to a method for detecting H 2 S near-infrared fluorescent molecular probe and its preparation method and application. Background technique [0002] Hydrogen sulfide (H 2 S), with the smell of rotten eggs. It is the third gas signal molecule discovered after NO and CO. Various physiological processes in living organisms play an important role. Numerous studies have confirmed that H 2 S has the functions of relaxing vascular smooth muscle, regulating neurotransmitters, inhibiting insulin signal, and regulating inflammation. H in vivo 2 High or low levels of S molecules often lead to a series of diseases, including Alzheimer's disease, Down's syndrome, diabetes and coronary heart disease. Therefore using efficient molecular tools to detect endogenous H 2 The molecular level of S is of great significance. [0003] Traditional detection H 2 Most of the fluo...

Claims

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Application Information

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IPC IPC(8): C07D405/06C09K11/06G01N21/64
CPCC07D405/06C09K11/06G01N21/6428C09K2211/1088C09K2211/1029C09K2211/1007
Inventor 刘熠杨世奎周方圆
Owner CHINA PHARM UNIV
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