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NBD-organic amine fluorescence probe, and preparation method and application thereof

A technology of fluorescent probes and organic amines, which is applied in the field of NBD-organic amine fluorescent probes and its preparation, which can solve the problems of inability to develop paper-based detection devices, color changes of colorimetric probes that cannot be seen by the naked eye in a short time, etc. question

Active Publication Date: 2017-04-19
BEIJING UNIV OF CHEM TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the color change of the current fluorescent and / or colorimetric probes cannot be seen by the naked eye in a short period of time, and most of them need to be detected by equipment detection, which cannot be developed into a paper-based detection device

Method used

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  • NBD-organic amine fluorescence probe, and preparation method and application thereof
  • NBD-organic amine fluorescence probe, and preparation method and application thereof
  • NBD-organic amine fluorescence probe, and preparation method and application thereof

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preparation example Construction

[0034] Another aspect of the present invention provides a kind of preparation method of NBD-organic amine fluorescent probe, this method comprises:

[0035] (1) In the presence of the first organic solvent and a basic condensing agent, the compound shown in formula (15) is contacted with NBD-Cl to react; the first intermediate product is obtained;

[0036]

[0037] (2) In the presence of the second organic solvent, trifluoroacetic acid is contacted with the first intermediate product to obtain the compound shown in formula (16);

[0038]

[0039] (3) In the presence of a third organic solvent, contact the compound represented by formula (16) with acetic anhydride to obtain the NBD-organic amine fluorescent probe.

[0040] Preferably, the molar ratio of the compound represented by the formula (15) to NBD-Cl is 1.0-1.5:1; the molar ratio of the compound represented by the formula (16) to acetic anhydride is 1:1.5-2.

[0041] According to the present invention, the alkalin...

Embodiment 1

[0052] (1) Dissolve 1.2mmol mono-tBOC piperazine and 1.0mmol NBD-Cl in 20.0mL dichloromethane solvent, then add 0.25mL (1.5mmol) N,N-diisopropylethylamine (DIPEA); room temperature After stirring for 4 hours, distill under reduced pressure, and use flash column chromatography to purify the residue under reduced pressure. The eluent is methanol and dichloromethane with a volume ratio of 1.5:100 to obtain an intermediate product

[0053](2) In 10 mL of dichloromethane, contact 10 mL of trifluoroacetic acid with the intermediate product obtained in step (1), stir at room temperature for 3 h, and distill under reduced pressure to obtain a red solid

[0054] (3) In 20mL of dichloromethane, 1.0mmol of Contact reaction with 1.8mmol acetic anhydride, stir at room temperature for 3h, distill under reduced pressure, use flash column chromatography to purify the residue under reduced pressure, the eluent is methanol and dichloromethane with a volume ratio of 0.8:100, to obtain the o...

Embodiment 2

[0057] Dissolve 0.5mmol piperidine and 0.75mmol NBD-Cl in 10.0mL tetrahydrofuran; then add 0.25mL (1.5mmol) N,N-diisopropylethylamine, stir at room temperature for 1h, distill under reduced pressure, use flash column chromatography The vacuum distillation residue was purified by analytical method, and the eluent was petroleum ether and dichloromethane at a volume ratio of 1:2 to obtain the NBD-organic amine fluorescent probe compound formula (9).

[0058] Compound (9) is a red solid, TLC: Rf = 0.3 (petroleum ether: dichloromethane = 1:2).1H NMR (400MHz, CDCl3), δ: 8.41 (d, J = 8.8Hz, 1H), 6.27 ( d,J=8.8Hz,1H),4.14-4.07(m,4H),1.86-1.80(m,6H).13C NMR(100MHz,DMSO-d6),δ:145.08,144.92,144.65,136.29,119.95, 103.05, 50.95, 25.80, 23.40. HRMS (ESI): m / z [M+H] + calcd. for C11H13N4O3: 249.0988, found: 249.0979.

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Abstract

The invention discloses an NBD-organic amine fluorescence probe, and a preparation method and an application thereof. The structure of the fluorescence probe is represented by formula (1); and in the formula (1), m is 0 or an integer in a range of 1 to 5, n is 0 or an integer in a range of 1 to 5, m and n cannot be 0 simultaneously, and R1 is CH2 or a group shown in the description. The fluorescence probe provided by the invention is a fluorescent / colorimetric double-channel probe, allows the chromogenic change to be directly observed by naked eyes, and realizes monitoring observation through using a paper-based detection device. The NBD-organic amine fluorescence probe can be used as an endogenous hydrogen sulfide probe to detect the existence of biological hydrogen sulfide.

Description

technical field [0001] The invention relates to the field of biological hydrogen sulfide detection, and more specifically, to an NBD-organic amine fluorescent probe and its preparation method and application. Background technique [0002] Hydrogen sulfide is an important endogenous signaling molecule with various biological functions. In different organs and tissues, hydrogen sulfide is cystathionine-β-synthase (CBS), cystathionine-γ-lyase (CSE) and 3-mercaptopyruvate thiotransferase (3-MPST) / In vivo enzymatic products of enzymatic reactions of three different pathways of cysteine ​​aminotransferase (CAT). In the central nervous system, the biological concentration of hydrogen sulfide is 50-160 μM. Sulfide levels in plasma plasma were 10-100 μM. Studies have shown that the level of hydrogen sulfide in the body is correlated with many diseases, such as Alzheimer's disease, Down syndrome, diabetes and liver cirrhosis. Although hydrogen sulfide has been considered to be as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/04C07D271/12C09K11/06G01N21/64
CPCC07D271/12C07D413/04C09K11/06C09K2211/1029C09K2211/1044C09K2211/1048G01N21/6486
Inventor 易龙席真
Owner BEIJING UNIV OF CHEM TECH
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