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Colorimetric fluorescence probe for high selectivity multiple biological thiol and preparation method thereof

A high-selectivity, fluorescent probe technology, applied in the field of life sciences, can solve the problems of inability to distinguish and identify the contents of cysteine, homocysteine ​​and glutathione, and achieve low cost and simple preparation methods Effect

Inactive Publication Date: 2010-11-24
BEIJING INSTITUTE OF TECHNOLOGYGY
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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 solve the problem that the prior art cannot distinguish and identify the content of cysteine, homocysteine ​​and glutathione in living cells, and propose a highly selective multivariate biothiol colorimetric fluorescent probe and its preparation method

Method used

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  • Colorimetric fluorescence probe for high selectivity multiple biological thiol and preparation method thereof
  • Colorimetric fluorescence probe for high selectivity multiple biological thiol and preparation method thereof
  • Colorimetric fluorescence probe for high selectivity multiple biological thiol and preparation method thereof

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Embodiment

[0030] 238.2mg (1mmol) 1,2-diaminoanthraquinone and 221.9mg (2mmol) selenium dioxide were ground respectively in an agate mortar, then the two compounds after grinding were mixed, continued to grind for 1h, and then The ground mixture was dissolved in chloroform, filtered, the solvent was evaporated under reduced pressure, the residue was separated by column chromatography, chloroform was used as eluent, and then the eluent was removed from chloroform eluent to obtain the target The pure product is 261.8 mg, the yield is 84%, and the reaction formula is as follows:

[0031]

[0032] The H NMR spectrum and high-resolution mass spectrometry characterization data of the target substance obtained are as follows:

[0033] 1 H-NMR (400MHz, DMSO-d 6 )δ(*10 -6 ): 7.95(t, J=7.0Hz, 2H), 8.20(d, J=7.6Hz, 2H), 8.34(d, J=2.8Hz, 2H);

[0034] HRMS (ESI positive): [M+H] + calcd for C 14 h 7 N 2 o 2 Se 314.96676, found 314.96644.

[0035] Identify and analyze the obtained target ...

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Abstract

The invention relates to a colorimetric fluorescence probe for high selectivity multiple biological thiol and a preparation method thereof, particularly to the colorimetric fluorescence probe which uses selenazole ring as an identification receptor, takes an anthraquinone derivant as an information report functional group, can high selectively distinguish and identify cysteine, homocysteine and glutathione and the preparation method thereof, belonging to the technical field of life science. The colorimetric fluorescence probe has the following structure formula as shown in the specification. The colorimetric fluorescence probe is prepared by grinding and reacting a diamine compound corresponding to the colorimetric fluorescence probe for the high selectivity multiple biological thiol and selenium dioxide in an agate mortar for 15-90 min at the grinding temperature of 10-35 DEG C, the mole ratio of the corresponding diamine compound to the selenium dioxide is 1:1-5, and the reaction formula is shown in the specification. The invention can directly distinguish and identify the cysteine, the homocysteine and the glutathione by eyes, and carry out imaging analysis on biological thiol in living cells. The invention has the advantages of simple method, environmental protection and industrial production.

Description

technical field [0001] The invention relates to a highly selective multi-component biothiol colorimetric fluorescent probe and a preparation method thereof, in particular to a class of highly selective region-specific probes that use selenazole rings as recognition receptors and anthraquinone derivatives as information reporting functional groups. A colorimetric fluorescent probe for distinguishing and recognizing cysteine, homocysteine ​​and glutathione and a preparation method thereof belong to the technical field of life sciences. Background technique [0002] Thiols are a very important class of substances in life systems and chemical sciences. Small molecule thiols are widely distributed in cells, plasma and tissues, and play an extremely important role in participating in important physiological activities and maintaining redox balance in organisms. Glutathione (GSH) is the most abundant small molecule thiol compound (1-10mM) in cells, which can combine with toxic com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D293/10G01N21/31G01N21/64
Inventor 张小玲朱宝存
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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