Hydrogen sulfide fluorescent probe as well as preparation method and application thereof

A fluorescent probe, hydrogen sulfide technology, applied in the field of analytical chemistry, can solve the problems of restriction, pretreatment to destroy cells or tissues, etc., to achieve high selectivity

A fluorescent probe, hydrogen sulfide technology, applied in the field of analytical chemistry, can solve the problems of restriction, pretreatment to destroy cells or tissues, etc., to achieve high selectivity

CN110734450AInactive Publication Date: 2020-01-31HEZHOU UNIV
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  • Hydrogen sulfide fluorescent probe as well as preparation method and application thereof
  • Hydrogen sulfide fluorescent probe as well as preparation method and application thereof
  • Hydrogen sulfide fluorescent probe as well as preparation method and application thereof

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Embodiment 1

[0050] A hydrogen sulfide fluorescent probe of the present invention, named 3'-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-6'-nitro-3H-spiro [Isobenzofuran-1,9'-xanthene]-3-one, molecular formula C 27 h 25 NO 9 , the structural formula is shown in formula (1):

[0051]

[0052] The preparation method of the hydrogen sulfide fluorescent probe of the above-mentioned present embodiment, its synthetic route is as follows figure 1 shown, including the following steps:

[0053] (1) 3'-hydroxyl-6'-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]-3H-spiro[ Isobenzofuran-1,9'-xanthene]-3-one:

[0054]

[0055] The reaction formula is as formula (2):

[0056]

[0057] The specific process is as follows: add fluorescein (6 g, 18 mmol) to a solution of sodium hydroxide (1.44 g, 36 mmol) in methanol (150 mL), and stir at room temperature until the fluorescein is completely dissolved. After dissolution, the solvent was distilled off under reduced pressure, and the residue was vacuum-d...

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Abstract

The invention relates to a hydrogen sulfide fluorescent probe as well as preparation and application thereof. The molecular formula of the fluorescent probe is C27H25NO9; the preparation method of thefluorescent probe comprises the following steps: reacting a fluorescein with sodium hydroxide; reacting an obtained product with 2-(2-(2-methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate to obtaina compound 4, reacting the compound 4 with N-Phenylbis(trifluoromethanesulphonimide) to obtain a compound 3, reacting the compound 3 with bis (pinacolato) diboron to obtain a compound 2, hydrolyzing the compound 2, and reacting an obtained product with tert-butyl nitrite to obtain the hydrogen sulfide fluorescent probe. The probe shows relatively high selectivity on detection of hydrogen sulfide in a pure water solution.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and relates to a hydrogen sulfide fluorescent probe preparation technology, in particular to a hydrogen sulfide fluorescent probe and its preparation method and application. Background technique [0002] Hydrogen sulfide (H 2 S) is a colorless, flammable, toxic gas with the smell of rotten eggs. However, studies have shown that hydrogen sulfide is the third gas signaling molecule after nitric oxide and carbon monoxide. As a gas signal molecule, endogenous hydrogen sulfide plays an important role in the physiological and pathological processes of organisms, such as controlling cell growth, protecting cardiovascular and cerebrovascular and stimulating angiogenesis, and can also be used as an antioxidant in the body. From another point of view, if the concentration of hydrogen sulfide in the body is disturbed, it will cause various diseases such as dementia, Down's syndrome, diabetes ...

Claims

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Application Information

Patent Timeline
31 Jan 2020
Publication
CN110734450A
IPC
C07D493/10; C09K11/06; G01N21/64
CPC
C07D493/10; C09K11/06; C09K2211/1088; G01N21/6428; G01N2021/6439
Inventors
朱东建; 白明少