Sulfydryl-containing fluorescent compound or thioester derivative thereof and preparation and application thereof

A technology of fluorescent compounds and derivatives, which is applied to the preparation of mercaptans, compounds containing elements of group 3/13 of the periodic table, fluorescence/phosphorescence, etc., can solve the problems of inapplicable NO dynamic detection and irreversible detection, and achieve good results. The effect of biomembrane permeability, excellent selectivity, and rapid detection response

Active Publication Date: 2020-06-12
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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  • Sulfydryl-containing fluorescent compound or thioester derivative thereof and preparation and application thereof
  • Sulfydryl-containing fluorescent compound or thioester derivative thereof and preparation and application thereof
  • Sulfydryl-containing fluorescent compound or thioester derivative thereof and preparation and application thereof

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 over 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. The reaction was monitored by thin-layer chromatography. After the end, the methanol was spun off, extracted twice with dichloromethane, the organic layers were combined,...

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 sulfydryl-containing fluorescent compound or a thioester derivative thereof and preparation and application thereof. The sulfydryl-containing fluorescent compound or the thioester derivative of the sulfydryl-containing fluorescent compound can emit strong fluorescence, the compund can directly react with nitric oxide or specifically and rapidly react with nitric oxide after the ester group is removed so as to generate the weak fluorescence product, and the quenched fluorescence can be gradually recovered to the initial level when the nitric oxide concentration is reduced so as to achieve the reversibility and the real-time dynamic detection on nitric oxide. The fluorescent probe is good in stability and can be stored and used for a long time; the detection signal-to-noise ratio is high, and the sensitivity is good; the compound has the advantages of good selectivity, good biofilm permeability, rapid detection reaction and reversibility of detection response andis suitable for real-time dynamic observation of endogenous nitric oxide in organisms such as solutions, intracellular organisms and living tissues. The structural formula of sulfydryl-containing fluorescent compound or the thioester derivative thereof is shown in the specification.

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 Applications(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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