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Preparation method of nitrogen-heterocyclic fluorescent probe and its application in hydrogen sulfide detection

A fluorescent probe and nitrogen heterocycle technology, which is applied in the preparation and application fields of fluorescent probes, can solve the problems of many reaction steps and mild reaction conditions, and achieves the effects of fewer reaction steps, mild reaction conditions, and increased weak alkalinity.

Active Publication Date: 2020-04-07
HEFEI INSTITUTES OF PHYSICAL SCIENCE - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to provide a preparation method of nitrogen-heterocyclic fluorescent probe and its application in the detection of hydrogen sulfide, so as to solve the problems of many reaction steps and mild reaction conditions in the preparation method in the prior art.

Method used

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  • Preparation method of nitrogen-heterocyclic fluorescent probe and its application in hydrogen sulfide detection
  • Preparation method of nitrogen-heterocyclic fluorescent probe and its application in hydrogen sulfide detection
  • Preparation method of nitrogen-heterocyclic fluorescent probe and its application in hydrogen sulfide detection

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Embodiment 1

[0040] In the prior art, the probes for detecting hydrogen sulfide are mainly aimed at H in vitro and in cytoplasm. 2 Detection of S. It is difficult to achieve endogenous H at the organelle level 2 Detection of S, especially lysosome-targeted H 2 Detection of S. To solve this technical problem, the invention provides a nitrogen heterocyclic fluorescent probe for detecting hydrogen sulfide in lysosomes. The nitrogen-heterocyclic fluorescent probe is based on 1,8-naphthalene dicarboxylic anhydride, and on the molecular structure of the parent, one side is linked with an azide group, and the other side is linked with a four-membered nitrogen-heterocyclic ring Teng Ning; The structural formula of the nitrogen-heterocyclic fluorescent probe is as follows:

[0041]

[0042] The nitrogen-heterocyclic fluorescent probes in this example have the advantages of good lysosome targeting, good water solubility, and high sensitivity, and realize rapid fluorescent signal response and ...

Embodiment 2

[0048] In order to obtain the nitrogen-heterocyclic fluorescent probe described in Example 1, we adopted the following preparation method to solve the problems of many reaction steps and mild reaction conditions in the existing preparation method.

[0049] refer to Figure 4 , a method for preparing a nitrogen heterocyclic fluorescent probe for detecting hydrogen sulfide in lysosomes, the preparation method comprising the following steps.

[0050] Step 1: Preparation of compound one.

[0051] Add 4-sulfonic acid-1,8-naphthalic anhydride potassium salt and thionyl chloride with a molar ratio of 1:40-1:120 into the reflux device one. At the same time, add 0.01-1 mL of N,N-dimethylformamide into the reflux device one. Then start the reflux device one. Stir the reaction under reflux for 6-24 hours to obtain reaction solution 1, and the reflux temperature is 65-80°C. After the reaction solution was cooled to room temperature, it was transferred to ice water, that is, in a fume ...

Embodiment 3

[0077] The nitrogen-heterocyclic fluorescent probe described in Implementation 1 will be prepared by the preparation method of Example 2, which can be applied to the specific detection of hydrogen sulfide in the water system, and qualitative or quantitative detection of the hydrogen sulfide; it can also be Applied to the detection of spontaneous or exogenous hydrogen sulfide in cell lysosomes. Specific application cases will be described below.

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Abstract

The invention discloses a preparation method of an azo-heterocyclic fluorescent probe and application of the azo-heterocyclic fluorescent probe in hydrogen sulfide detection. A synthetic method to synthesize the azo-heterocyclic fluorescent probe is simple, has few reaction steps, employs cheap materials and has mild reaction conditions. The azo-heterocyclic fluorescent probe prepared herein can detect cellular endogenous and exogenous H2S and provide fluorescence imaging; the azo-heterocyclic fluorescent probe can detect H2S in cytolysosome and provide fluorescence imaging. Azo-heterocyclic molecules in the probe herein help improve water solubility of the probe and weak basicity, so that the probe herein has the advantages of good lysosome-targeting performance, good water solubility, high sensitivity and the like, and can provide quick fluorescent signal response for hydrogen sulfide in lysosomes and real-time visual monitoring for the hydrogen sulfide.

Description

technical field [0001] The invention relates to the technical field of preparation and application of fluorescent probes, in particular to a nitrogen-heterocyclic fluorescent probe for detecting hydrogen sulfide in lysosomes, a method for preparing the nitrogen-heterocyclic fluorescent probe, and a nitrogen-heterocyclic fluorescent probe Application in detection of hydrogen sulfide. Background technique [0002] Hydrogen sulfide (H 2 S) is the third gas signal molecule discovered endogenously produced by organisms after nitric oxide (NO) and carbon monoxide (CO), mainly produced by L-cystine through cystathionine-β-synthase ( cystathionine-β-synthase (CBS), cystathionine-γ-lyase (cystathionine-γ-lyase, CSE) and other biological enzymes are endogenously produced. h 2 S plays an important role in regulating normal physiological processes such as the cardiovascular system, nervous system, immune system, endocrine system, respiratory system, and gastrointestinal system. Abno...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/06C09K11/06G01N21/64
CPCC07D401/06C09K11/06C09K2211/1029C09K2211/1074G01N21/6486
Inventor 王振洋赵君杨林林王建萍韩光梅
Owner HEFEI INSTITUTES OF PHYSICAL SCIENCE - CHINESE ACAD OF SCI
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