Fluorescent probe for detecting reduced nicotinamide adenine dinucleotide and phosphate ester of reduced nicotinamide adenine dinucleotide and preparation method and application of fluorescent probe

A technology of nicotinamide adenine and fluorescent probe, applied in the field of fluorescence chemistry, to achieve the effect of reducing the impact

Active Publication Date: 2019-08-09
ZHOUKOU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

After literature research, it was found that ratiometric fluorescent probes for the detection of NAD(P)H have not been reported

Method used

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  • Fluorescent probe for detecting reduced nicotinamide adenine dinucleotide and phosphate ester of reduced nicotinamide adenine dinucleotide and preparation method and application of fluorescent probe
  • Fluorescent probe for detecting reduced nicotinamide adenine dinucleotide and phosphate ester of reduced nicotinamide adenine dinucleotide and preparation method and application of fluorescent probe
  • Fluorescent probe for detecting reduced nicotinamide adenine dinucleotide and phosphate ester of reduced nicotinamide adenine dinucleotide and preparation method and application of fluorescent probe

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preparation example Construction

[0024] The preparation method of the fluorescent probe for detecting reduced nicotinamide adenine dinucleotide and its phosphate ester as described above comprises the following steps: combining 7-diethylaminocoumarin and 1,2,3,3-tetra Add methyl-6-nitro-3H-indolium iodide into the reactor, after vacuum / nitrogen replacement, add absolute ethanol, heat under reflux and stir for 10-15h under the protection of nitrogen, and concentrate and evaporate the reaction solution to obtain a solid The target compound was purified by silica gel column chromatography. The mobile phase of column chromatography was petroleum ether and ethyl acetate, and the volume ratio was 5:1.

[0025] The molar ratio of 7-diethylaminocoumarin to 1,2,3,3-tetramethyl-6-nitro-3H-indolium iodide is 1:(1-1.2).

[0026] For example, the application of the above-mentioned fluorescent probe in the detection of reduced nicotinamide adenine dinucleotide and its phosphate ester, the detection method is as follows: ad...

Embodiment 1

[0030] The preparation method of the fluorescent probe that detects reduced nicotinamide adenine dinucleotide and phosphate thereof, concrete steps are as follows: add 0.245g 7-diethylaminocoumarin (compound 1, 1.0mmol ) and 0.346g1,2,3,3-tetramethyl-6-nitro-3H-indolium iodide (compound 2, 1.0mmol), vacuum / nitrogen replacement 3 times, adding 20ml absolute ethanol, nitrogen protection It was heated under reflux and stirred for 12 hours, then concentrated and evaporated, and the resulting solid was purified by silica gel column chromatography to obtain the target compound fluorescent probe A, a dark blue solid. The mobile phase of column chromatography was petroleum ether and ethyl acetate with a volume ratio of 5:1.

[0031] The hydrogen spectrum data of fluorescent probe A are as follows: 1 HNMR (400MHz, CDCl 3)δ (ppm) 10.15 (s, 1H), 8.68 (d, J = 8.69Hz, 1H), 8.45 (d, J = 8.44Hz, 1H), 8.33 (s, 1H), 8.17 (d, J = 8.16 Hz,1H),7.95(d,J=7.97Hz,1H),7.64(d,J=7.63Hz,1H),6.76(d,J=6...

Embodiment 2

[0048] The preparation method of the fluorescent probe that detects reduced nicotinamide adenine dinucleotide and its phosphate, concrete steps are as follows: add 0.245g 7-diethylaminocoumarin (compound 1, 1.0mmol ) and 0.381g1,2,3,3-tetramethyl-6-nitro-3H-indolium iodide (compound 2, 1.1mmol), vacuum / nitrogen replacement 3 times, adding 20ml absolute ethanol, nitrogen protection It was heated under reflux and stirred for 10 h, then concentrated and evaporated, and the resulting solid was purified by silica gel column chromatography to obtain the target compound fluorescent probe A, a dark blue solid. The mobile phase of column chromatography was petroleum ether and ethyl acetate with a volume ratio of 5:1.

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Abstract

The invention discloses a preparation method of a fluorescent probe for detecting reduced nicotinamide adenine dinucleotide and phosphate ester of the reduced nicotinamide adenine dinucleotide. The method includes the following steps that 7-diethylamino coumarin and 1,2,3,3-tetramethyl-6-nitro-3H-indolium iodide are added into a reactor, absolute ethyl alcohol is added after vacuum/nitrogen replacement, hot reflux stirring is carried out on 10-15 hours under nitrogen protection, the reaction liquid is concentrated and evaporated, and a target compound is obtained by purifying the obtained solid through silica gel column chromatography. According to the method, the 7-diethylamino coumarin and the 1,2,3,3-tetramethyl-6-nitro-3H-indolium iodide serve as a fluorescent matrix, and on the basisof an H selective nucleophilic addition specific cyanine derivative on NAD(P)H, a whole conjugated system is changed, so that the pushing-drawing electron capacity in molecules is influenced, and selective detection of NAD(P)H is realized by utilizing the fluorescence wavelength difference between reactants and products.

Description

technical field [0001] The invention belongs to the technical field of fluorescence chemistry, and in particular relates to a fluorescent probe for detecting reduced nicotinamide adenine dinucleotide and its phosphoric acid ester, and a preparation method and application of the fluorescent probe. Background technique [0002] Reduced nicotinamide adenine dinucleotide (NADH), also known as reduced coenzyme I, and its phosphate ester (NADPH), play an important role as a cofactor in many biocatalytic processes, including energy metabolism , mitochondrial function, immune function, biosynthesis, gene expression, calcium homeostasis, cell death, aging and carcinogenesis, etc. (Alberghina L, Gaglio D. Cell Death Dis, 2014, 5, 1561). Their bioconcentration levels are associated with diseases such as tumors and anemia, diabetes, cancer and epilepsy (Strryerl, Biochemistry, 3rd ed, Wiley, New York, 1988). Over the past few decades, considerable efforts have been made to examine NAD(...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06C09K11/06G01N21/64
CPCC07D405/06C09K11/06G01N21/6428G01N21/64C09K2211/1029C09K2211/1088G01N2021/6421
Inventor 田丰收张洁陈亚红
Owner ZHOUKOU NORMAL UNIV
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