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Fluorescent probe for detecting glutathione reductase and bioactive sulfhydryl compound as well as synthesis method and application thereof

A technology of mercapto compounds and biological activity, which is applied in the fields of mercury organic compounds, chemical instruments and methods, biological testing, etc., and can solve the problems that chemical sensing molecules are rarely reported.

Inactive Publication Date: 2009-12-02
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Due to their large molar extinction coefficient and high fluorescence quantum yield, coumarin compounds have been used as fluorescent markers in biotechnology to some extent, but they are used as chemical sensing molecules directly used to identify specific objects. Examples are rarely reported

Method used

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  • Fluorescent probe for detecting glutathione reductase and bioactive sulfhydryl compound as well as synthesis method and application thereof
  • Fluorescent probe for detecting glutathione reductase and bioactive sulfhydryl compound as well as synthesis method and application thereof
  • Fluorescent probe for detecting glutathione reductase and bioactive sulfhydryl compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] (1) Dissolve 2.5g of 7-N, N-diethylaminocoumarin-3-aldehyde in dry methanol, slowly add 3.5g of o-mercaptoaniline dropwise under stirring and reflux reaction, filter after stirring and reflux reaction for 5 hours, and The obtained solid was vacuum-dried to obtain the probe precursor (II-1) with a yield of 87%.

[0073] EI-MS, m / e, 319.1[M+1] + .λ ab. max / nm=390nm.

[0074] (2) Dissolve 3 g of the probe precursor (II-1) in dry chloroform, and slowly add 2 g of HgCl dropwise under ice bath conditions 2 , stirred and refluxed for 3 hours to obtain a red solid. After filtration, the red solid was vacuum-dried at room temperature, and then crystallized with ethanol to obtain a red needle-shaped fluorescent probe (I-1), with a yield of 85%. EI-MS, m / e, 590.1[M+1] + .λ ab. max / nm=490nm.

[0075]

[0076] Structure of Fluorescent Probe I-1

[0077] Add the fluorescent probe (I-1) to various enzymes or proteins (see Figure 1b ) solution, by Figure 1a It can be s...

Embodiment 2

[0080] (1) Dissolve 2.7g of 7-N, N-dimethylaminocoumarin-3-aldehyde in dry methanol, slowly add 5g of o-mercaptoaniline dropwise under stirring at room temperature, reflux and stir for 8 hours, then filter, and dry under vacuum at room temperature The probe precursor (II-2) was obtained after the solid, and the yield was 78%.

[0081] EI-MS, m / e, 287.1[M+1] + .λ ab. max / nm=390nm.

[0082] (2) Dissolve 3.6g of the probe precursor (II-2) in dry chloroform, and slowly add 2g of HgCl dropwise under ice bath conditions 2 After 7 hours of stirring and reflux reaction, a red solid was obtained. After filtration, the red solid was vacuum-dried at room temperature, and then crystallized with a mixture of tetrahydrofuran (THF) and ether (volume ratio 2: 1) to obtain a red needle-shaped fluorescent probe (I- 2), the yield is 90%.

[0083] EI-MS, m / e, 558.1[M] + .λ ab. max / nm=487nm.

[0084]

[0085] Structure of fluorescent probe I-2

Embodiment 3

[0087] (1) Dissolve 25g of 7-N, N-dimethylamino-4-methylcoumarin-3-aldehyde in dry methanol, slowly add 32g of o-mercaptoaniline dropwise under stirring at room temperature, and filter after stirring for 4 hours. The obtained solid was vacuum dried to obtain the probe precursor (II-3) with a yield of 61%.

[0088] EI-MS, m / e, 302.2[M+1] + .λ ab. max / nm=390nm.

[0089] (2) Dissolve 13g of the probe precursor (II-3) in dry chloroform, and slowly add 10g of HgCl dropwise under ice bath conditions 2 , a red solid was obtained after stirring and reacting for 7 hours. After filtration, the red solid was vacuum-dried at room temperature, and then crystallized with a mixture of THF:ether (volume ratio 2:1) to obtain a red needle-like crystal fluorescent probe (I-3), producing The rate is 87%.

[0090] EI-MS, m / e, 573.1[M+1] + .λ ab. max / nm=481nm.

[0091]

[0092] Structure of fluorescent probe (I-3)

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Abstract

The invention relates to a fluorescent probe for detecting glutathione reductase and a bioactive sulfhydryl compound as well as a synthesis method and application thereof. In the invention, a coumarin-3-carbonyl compound with substitutional groups R1, R2, R3 and R4 is dissolved in a dry organic solvent, and o-aminothiophenol with a substitutional group R5 is slowly dropped into the mixture at room temperature or circumfluence temperature; the mixture is stirred and filtered, the organic solvent is removed, and then a probe precursor is obtained after a solid is obtained by vacuum drying; the probe precursor is dissolved in the dry organic solvent, and HgX2 is slowly dropped into the mixture under an ice bath condition; and the mixture is stirred to obtain a red solid deposit, a red solid is obtained by vacuum drying after the red solid deposit is filtered, then diffusion crystallization is carried out by using the organic solvent, and a red acicular crystal of formula (I) is obtained, i.e. the fluorescent probe. The fluorescent probe has favourable selectivity to the glutathione reductase and the bioactive sulfhydryl compound, and is suitable for the fast detection of the glutathione reductase and the bioactive sulfhydryl compound.

Description

technical field [0001] The invention relates to detection of glutathione reductase and biologically active sulfhydryl compounds, in particular to a fluorescent probe for detection of glutathione reductase and its synthesis method and application. Background technique [0002] A large number of studies have shown that the whole blood glutathione reductase activity coefficient (BGRAC) is an effective way to evaluate the body's vitamin B 2 It is a specific and sensitive indicator of nutritional status, which can not only reflect the metabolism and utilization of vitamins in the body, but also the marginal deficiency state of storage. And not affected by other malnutrition. Whole blood glutathione reductase is responsible for the important task of regulating oxidized glutathione and reduced glutathione in the body. [0003] At present, the analysis and determination of glutathione reductase is generally based on its reducing property and its reaction with some organic reagents...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F3/14C07D417/04G01N33/52
Inventor 汪鹏飞盛瑞隆刘卫敏张洪艳
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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