A kind of hydrogen sulfide fluorescent probe and its preparation method and application

A fluorescent probe, hydrogen sulfide technology, applied in chemical instruments and methods, fluorescence/phosphorescence, organic chemistry, etc., can solve problems such as probe interference, consumption, and probe drop

Active Publication Date: 2022-05-06
XUCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, many research groups at home and abroad have synthesized many excellent fluorescent probes using the unique shape of H2S, but there are still some problems, mainly: ① how to avoid the interference and consumption of biothiols on the probe; ② how to reduce the probe The detection limit achieves low concentration detection of H2S

Method used

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  • A kind of hydrogen sulfide fluorescent probe and its preparation method and application
  • A kind of hydrogen sulfide fluorescent probe and its preparation method and application
  • A kind of hydrogen sulfide fluorescent probe and its preparation method and application

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Embodiment 1

[0032] The preparation process of the fluorescent probe in this embodiment specifically includes the following steps:

[0033] (1) Preparation of compound 1

[0034] Add 5mLN,N-dimethylformamide (DMF) to a 25mL two-necked flask, then slowly add 2mL (20mmol) phosphorus oxychloride (POCl3) into the two-necked flask with a constant pressure funnel at 0°C (within 5min dropwise), after stirring for 30min, add 0.2mL N, N-dimethylformamide and 0.3535g (2mmol) 6-methoxy-1-tetralone, stir for 5min, then slowly heat up to 90-95°C, Stirring was continued for 5 h to obtain a reaction liquid; a large amount of viscous solid appeared after cooling with ice water, and compound 1 was obtained by vacuum filtration and vacuum drying with a yield of 75%. 1H NMR (400MHz, CDCl3) δ7.27(s, 1H), 530(s, 1H), 3.72(q, J=7.0Hz, 2H), 3.49(s, 1H), 3.19-3.09(m, 3H) , 1.90(dt, J=11.4, 5.8Hz, 3H), 1.73-1.61(m, 2H), 1.25(t, J=7.0Hz, 3H), 0.94-0.77(m, 1H), 0.07(s, 1H ).

[0035] The synthetic route is as fo...

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Abstract

The invention belongs to the technical field of organic synthesis, and in particular relates to a hydrogen sulfide fluorescent probe and a preparation method and application thereof. The structural formula of the fluorescent probe is as follows: . The fluorescent probe of the invention uses a benzothiazole derivative as a fluorophore, and the thiol structure is a specific reaction group for hydrogen sulfide; the probe itself has strong fluorescence, and the fluorescence is weakened after reacting with hydrogen sulfide, and can be used for the detection of hydrogen sulfide. The probe is relatively stable in reaction to hydrogen sulfide, has good selectivity and high sensitivity, and can be used for fluorescence detection for determining the content of hydrogen sulfide in biological and environmental systems.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a hydrogen sulfide (H2S) fluorescent probe and a preparation method and application thereof. Background technique [0002] As the most important gas transporter, hydrogen sulfide has many important physiological functions in regulating cardiovascular, nervous, endocrine, immune, and gastrointestinal systems. Furthermore, H2S acts as a scavenger of endogenous reactive oxygen species (ROS). However, abnormal concentrations of H2S are associated with various human diseases, including symptoms such as Down syndrome, hypertension and diabetes. Volatility, lipophilicity, diffusivity, high reactivity, and complex reactions involving H2S make the detection of H2S in biological systems very difficult. Hydrogen sulfide is an essential molecule in cells, plays an important antioxidant role during damage and oxidative stress, is a chelating agent that binds and intera...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/64C09K11/06G01N21/64
CPCC07D277/64C09K11/06G01N21/6428C09K2211/1037C09K2211/1011
Inventor 许志红侯旭锋张文凯翟姚高志颖刘源汪坪杨金刚
Owner XUCHANG UNIV
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