Sulfhydryl-containing fluorescent compound or its thioester derivatives and its preparation and application

A technology of fluorescent compounds and derivatives, which is applied in the preparation of thiols, compounds containing Group 3/13 elements of the periodic table, fluorescence/phosphorescence, etc. It can solve the problems of irreversible detection, inappropriate NO dynamic detection, etc. Selectivity, good biofilm permeability, high detection signal-to-noise ratio

Active Publication Date: 2021-07-09
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Even so, the currently reported probes all recognize and respond to NO through an irreversible reaction, and cannot detect NO reversibly.
Since the concentration and expression localization of biological NO are in dynamic changes, these probes are not suitable for dynamic detection of NO

Method used

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  • Sulfhydryl-containing fluorescent compound or its thioester derivatives and its preparation and application
  • Sulfhydryl-containing fluorescent compound or its thioester derivatives and its preparation and application
  • Sulfhydryl-containing fluorescent compound or its thioester derivatives and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: the preparation of I-1

[0033]

[0034] Compound 1a is reacted with cystamine in dry dichloromethane under the condition of peptide synthesis condensing agent (such as HBTU). After the end, add ethyl acetate to dilute, wash twice with saturated aqueous sodium bicarbonate solution, saturated aqueous ammonium chloride solution, and saturated saline, and dry the organic phase with anhydrous sodium sulfate, spin dry, and wash with methanol-containing chloroform solution (1 %-10% methanol, gradient elution) as the eluent for silica gel column chromatography purification to obtain 1b (82%), high resolution mass spectrum HRMS: 547.2113 (M+H) + .

[0035] Intermediate 1b was redissolved in methanol, dithiothreitol was dissolved in water, added to the system, and reacted at room temperature. Thin-layer chromatography monitors the reaction. After the end, the methanol is spun off, extracted twice with dichloromethane, the organic layers are combined, dried ove...

Embodiment 2

[0036] Embodiment 2: the preparation of I-2

[0037]

[0038] Add triethylamine to compound 2a and cystamine in dry dichloromethane, and stir at room temperature. After the reaction was completed, pure water and saturated brine were added to wash twice, the organic phase was dried over anhydrous sodium sulfate, spin-dried, and purified by column chromatography to obtain 2b (93%). Mass Spectrum m / z 618.15(M+H) + .

[0039] Referring to the synthesis of compound I-1, 2b was reduced to prepare I-2 with a yield of 80%. High resolution mass spectrum 311.0935(M+H) + .

Embodiment 3

[0040] Embodiment 3: the preparation of I-3

[0041]

[0042] Compound 3a was dissolved in ethanol, added cystamine, and refluxed. After the reaction was complete, it was cooled and filtered with suction to obtain 3b as a yellow solid. Yield 60%. Mass Spectrum m / z 621.20 (M+Na) + .

[0043] Referring to the synthesis of compound I-1, I-3 was prepared by reducing 3b with a yield of 85%. High resolution mass spectrum 301.0989(M+H) + .

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PUM

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Abstract

The invention provides a fluorescent compound containing a mercapto group or a thioester derivative thereof as well as its preparation and application. The mercapto-containing fluorescent compound or its thioester derivatives of the present invention can emit strong fluorescence, but can react with nitric oxide directly or quickly after removing the ester group to generate products with weak fluorescence. When the nitrogen concentration decreases, the quenched fluorescence can gradually return to the initial level, thereby realizing the reversible and real-time dynamic detection of nitric oxide. The fluorescent probe of the present invention has good stability and can be stored and used for a long time; the detection signal-to-noise ratio is high, the sensitivity is good; the selectivity is good, the biofilm permeability is good, the detection response is fast, the detection response is reversible, and it is suitable for solution Real-time dynamic observation of endogenous nitric oxide in organisms, such as cells and living tissues. The structural formula of the mercapto-containing fluorescent compound or its thioester derivatives is:

Description

technical field [0001] The invention belongs to the field of biological detection, and relates to a class of fluorescent compounds containing mercapto groups or their thioester derivatives and their preparation and application. The application of fluorescent probe molecules and the application of nitric oxide dynamic changes in living cells. Background technique [0002] Nitric oxide (NO) is an important endogenous reactive nitrogen species in biological systems, and it is also an important signaling molecule. It is mainly produced from L-arginine in mammalian cells through deazurization of guanidinium group catalyzed by nitric oxide synthase. In 1977, NO was first discovered in vascular smooth muscle, and it was defined as an endothelium-derived relaxing factor in 1987. In the past few decades, with the deepening of research, it has been found that NO not only has important physiological significance in the vascular system, but also has different functions in the immune s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/49C07C323/42C07C319/06C07C327/30C07D221/14C07D311/88C07F5/05C07D311/16C07D491/16C09K11/06G01N21/64A61K49/00
CPCA61K49/0021C07C323/42C07C323/49C07C327/30C07D221/14C07D311/16C07D311/88C07D491/16C07F5/05C09K11/06C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1055C09K2211/1088G01N21/6402
Inventor 李新李佳胡永洲臧奕郭瑞张雨恬
Owner ZHEJIANG UNIV
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