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Reactive-type fluorescence probe for distinguishing sulfydryl compounds, synthesis method and application thereof

A technology of thiol compounds and fluorescent probes, which is applied in chemical instruments and methods, fluorescence/phosphorescence, analytical materials, etc., to achieve the effects of small molecular weight, simple and easy preparation method, and good cell compatibility

Active Publication Date: 2017-08-29
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

However, since Cys and Hcy have similar structures and activities, most probes can specifically recognize Cys or Hcy according to the different activities of their five-membered or six-membered rings (Aabha Barve, Mark Lowry, Jorge O. Escobedo , Katherine T. Huynh, Lovemore, Hakuna and Robert M, Strongin. Differences in heterocycle basicity distinguishing homocysteine ​​from cysteine ​​using aldehyde-bearing fluorophores. Chem. Commun. 2014, 50, 8219-8222; Hye Yeon Lee, Yoon Pyo Choi, Sunkyung Kim , Zhiqian Guo, Songyi Lee, K.M.K.Swamy, Gyougmi Kim, JinYong Lee, Injae Shin and Juyoung Yoon. Selective homocysteine ​​turn-onfluorescent probes and their bioimaging applications. 2014, 50, 6967-6969; Lijun Tang, Jianze Shi, Zhenlong Huang Yan, Qiang Zhang, Keli Zhong, Shuhua Hou and Yanjiang Bian. An ESIPT-based fluorescent probe for selective detection of homocysteine ​​and its application in live-cell imaging. 2016, 57, 5227-5231.), but can effectively distinguish their fluorescence at the same time Probes have not been reported yet

Method used

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  • Reactive-type fluorescence probe for distinguishing sulfydryl compounds, synthesis method and application thereof
  • Reactive-type fluorescence probe for distinguishing sulfydryl compounds, synthesis method and application thereof
  • Reactive-type fluorescence probe for distinguishing sulfydryl compounds, synthesis method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0033] Synthesis of embodiment 1 fluorescent probe (I-1)

[0034] The synthetic method of fluorescent probe (I-1), comprises the following steps:

[0035] Dissolve 0.8 mM 7-julonidinecoumarin-3-aldehyde and 1 mM (1,3-dioxolan-2-yl)methyltriphenylphosphine bromide in 8 mL of dry CH 2 Cl 2 , stirred at room temperature for 0.5h; then slowly added 0.5mL of 0.3g / mL NaOH solution, stirred at room temperature for 9h; then added 1mL of concentrated HCl, stirred for 20min, and spin-dried the solvent to obtain a crude orange-yellow probe, which was analyzed by column chromatography Separation on silica gel to obtain fluorescent probe (I-1), ESI-MS: m / z[C 18 h 16 ClNO 3 +H] + :330.1.

[0036]

Embodiment 2

[0037] Synthesis of embodiment 2 fluorescent probe (I-2)

[0038] The synthetic method of fluorescent probe (I-2), comprises the following steps:

[0039] Dissolve 0.8 mM 7-N,N-diethylcoumarin-3-aldehyde and 1.5 mM (1,3-dioxolan-2-yl)methyltriphenylphosphine bromide in 8 mL of dry CH 2 Cl 2 , stirred at room temperature for 0.6h, then slowly added 0.23mL of 0.3g / mL NaOH solution, stirred at room temperature for 10h; then added 1.15mL of concentrated HCl, stirred for 30min, and spin-dried the solvent to obtain a crude orange-yellow probe, which was analyzed by column chromatography Separation on silica gel to obtain fluorescent probe (I-2), ESI-MS: m / z[C 16 h 16 ClNO 3 +H] + :306.1.

[0040]

Embodiment 3

[0041] Synthesis of embodiment 3 fluorescent probe (I-3)

[0042] The synthetic method of fluorescent probe (I-3), comprises the following steps:

[0043] Dissolve 0.8 mM 7-N,N-dihexylcoumarin-3-aldehyde and 2 mM (1,3-dioxolan-2-yl)methyltriphenylphosphine bromide in 8 mL of dry CH 2 Cl 2 , stirred at room temperature for 0.8h, then slowly added 0.85mL of 0.3g / mL NaOH solution, stirred at room temperature for 8h; then added 0.85mL of concentrated HCl, stirred for 22min, and spin-dried the solvent to obtain a crude orange-yellow probe. Analysis of silica gel separation, to obtain fluorescent probe (I-3), ESI-MS: m / z[C 24 h 32 ClNO 3 +H] + :418.2.

[0044]

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PUM

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Abstract

The invention discloses a reactive-type fluorescence probe for distinguishing sulfydryl compounds, wherein the structure of the fluorescence probe is represented as the formula (I). R1, R2, R3 and R4 are independently selected from one of hydrogen, a C1-C8 alkyl group and a C3-C8 cycloalkyl group, and X is independently selected from halogens; or the R1 and the R4 and / or the R2 and the R3 can form a ring. The invention also discloses a synthesis method and an application of the fluorescence probe. The fluorescence probe is low in molecular weight, is high in fluorescent quantum yield, has good cytocompatibility, can generate different fluorescence enhancement signals when being reacted respectively with cysteine and homocystine, can distinguish and recognize the cysteine and homocystine well, has good stability and is easy to prepare.

Description

technical field [0001] The invention relates to the technical field of biological detection. More specifically, it relates to a reactive fluorescent probe for distinguishing sulfhydryl compounds and its synthesis method and application. Background technique [0002] Fluorescence analysis has attracted widespread attention due to its advantages of simple operation, high sensitivity, good selectivity, real-time detection, and little damage to organisms. Medicine has proved that changes in the concentration of certain amino acids in the body are closely related to human health. For example, the lack of Cys can lead to skin damage, slow growth and hair decolorization, while the abnormal concentration of Hcy can cause cardiovascular diseases, osteoporosis and inflammatory bowel disease, etc. . Therefore, the detection and quantification of amino acids is very important. However, since Cys and Hcy have similar structures and activities, most probes can specifically recognize Cy...

Claims

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Application Information

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IPC IPC(8): C07D491/20C07D311/16C09K11/06G01N21/64
CPCC07D311/16C07D491/20C09K11/06C09K2211/1029C09K2211/1088G01N21/6486
Inventor 刘卫敏李英汪鹏飞张洪艳吴加胜葛介超
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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