Preparation method and application of mercaptan fluorescence probe based on coumarin

A technology of coumarin hydrazide and fluorescent probe, which is applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems such as difficult to distinguish, and achieve low cytotoxicity, good selectivity, and good photochemical stability Effect

Active Publication Date: 2016-06-29
XINXIANG MEDICAL UNIV
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Problems solved by technology

[0005] At present, most of the probes for detecting thiols are to detect the total amount of thiol compounds, such as fluorescent probes that use the nucleophilicity of thiol groups in thiol compounds to detect thiols, and use the redox reaction between thiol groups and disulfide bo

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  • Preparation method and application of mercaptan fluorescence probe based on coumarin
  • Preparation method and application of mercaptan fluorescence probe based on coumarin
  • Preparation method and application of mercaptan fluorescence probe based on coumarin

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Embodiment Construction

[0035] The present invention will be described in detail below in conjunction with the accompanying drawings.

[0036] The instruments and reagents used in the present invention were obtained from commercial sources unless otherwise specified.

[0037] 1 Experimental part

[0038] 1.1 Materials and reagents

[0039] p-tert-butylphenol, trifluoroacetic acid, 4-diethylamino salicylaldehyde, piperidine, absolute ethanol, diethyl malonate, dichloromethane, ethyl acetate, acetonitrile, hydrazine hydrate, hexamethylene Tetramine, NaOH, HCl, anhydrous Na 2 SO 4 , L-cysteine, N-acetyl-cysteine, L-homocysteine, glutathione, L-tryptophan, L-glycine, L-lysine, L-histidine Acid, L-alanine, L-valine, L-proline, L-phenylalanine, methionine, serine, threonine, aspartic acid, arginine, leucine, isoleucine All the above reagents were of analytical grade. Fetal bovine serum, penicillin, DMEM medium.

[0040] 1.2 Main instruments

[0041] Three-purpose UV Analyzer, UV-Vis Spectrophotomet...

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Abstract

The invention discloses a preparation method and application of a mercaptan fluorescence probe based on coumarin. The preparation method includes: coumarin and p-tert-butylphenol dialdehyde are used as raw materials to synthesize a bis-Schiff base coumarin derivative (compound I), the compound I has strong fluorescence, and the compound I is coordinated with copper ions to prepare coumarin-copper ion (II) complex, namely the mercaptan fluorescence probe I-Cu (II). Due to the influence of the paramagnetism of Cu2+ and photoinduction electron transfer effect, the fluorescence of the compound I is quenched; sulfur atoms in compounds such as mercapto-amino acid and derivatives such as glutathione thereof and Cu2+ have a strong coordination effect, the competitive coordination effect allows the copper ions in the coumarin-copper ion (II) complex to be taken away by the mercapto-amino acid and the derivatives thereof so as to regenerate the compound I, and the fluorescence of the compound I is restored. Accordingly, a method for fast and simply detecting mercaptan compounds is built.

Description

technical field [0001] The invention relates to a thiol detection technology, in particular to a preparation method and application of a coumaryl hydrazide-based thiol fluorescent probe. Background technique [0002] Sulfhydryl (-SH) has high chemical activity in cells. Glutathione (L-γ-glutamyl-L-cysteinyl-glycine, glutathione) is a biologically active tripeptide compound with both glutamyl and sulfhydryl groups. Clinically, glutathione can rapidly improve the body's immunity, and has good effects in anti-oxidation, anti-radiation, scavenging free radicals, detoxification, and promoting iron absorption without side effects. It plays an important role in many cellular functions such as intracellular redox activity, metabolism of xenobiotics, intracellular signal transduction and gene regulation. Glutathione has a strong protective effect on symptoms such as leukopenia caused by radiation and radiopharmaceuticals. There are many diseases, such as early arteriosclerosis, lu...

Claims

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Application Information

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IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06C09K2211/1088G01N21/643G01N2021/6432
Inventor 何广杰李静杨璐薛爱荣张伟千新来徐国英
Owner XINXIANG MEDICAL UNIV
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