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Lysosome-targeted Cys near-infrared fluorescent probe and preparation method and application thereof

A fluorescent probe and near-infrared technology, applied in the field of analysis and detection, can solve the problems of detection interference and short emission wavelength, and achieve the effects of fast detection, high sensitivity and novel structure

Active Publication Date: 2020-08-07
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, a large number of fluorescent probes for detecting Cys have been reported (Wang Jun, Hu Liangjun, Shen Jing, Jiang Jiquan, Yu Keyong, Sun Rongguo. Research progress of L-cysteine ​​visual sensor / system, organic Chemistry, 2018, 38:760-774), but because there are other biothiols similar to Cys in structure and reactivity in biological systems, such as homocysteine ​​(Hcy) and reduced glutathione (GSH) , more or less interferes with the detection of Cys, and the emission wavelength of most fluorescent probes is relatively short, so there are limitations that cannot be applied in vivo

Method used

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  • Lysosome-targeted Cys near-infrared fluorescent probe and preparation method and application thereof
  • Lysosome-targeted Cys near-infrared fluorescent probe and preparation method and application thereof
  • Lysosome-targeted Cys near-infrared fluorescent probe and preparation method and application thereof

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Effect test

Embodiment 1

[0030] Example 1: 3-(2-(3-(dicyanomethylene)-5,5-dimethylcyclohexen-1-yl)vinyl)-4-morpholinocoumarin-7 - the preparation of acrylate, its reaction formula is as figure 1 shown.

[0031] (1) Preparation of 4,7-dihydroxycoumarin: resorcinol (50 mmol, 5.505 g), malonic acid (60 mmol, 6.244 g) and anhydrous zinc chloride (161.5 mmol, 22.009 g ) into 16.5 mL of phosphorus oxychloride, then heated to 60-65 °C and stirred for 12 hours, cooled, added 200 mL of ice water to quench the reaction, filtered, and the obtained solid was dissolved in 5% sodium carbonate aqueous solution, and dilute The pH was adjusted to 3-4 with hydrochloric acid, and a yellow solid was precipitated, which was filtered to obtain 6.95 g of 4,7-dihydroxycoumarin, with a yield of 78%. 1 H NMR (600 MHz, DMSO- d 6 ) δ 12.23 (s, 1H), 10.52 (s, 1H), 7.63 (d, J = 8.6Hz, 1H), 6.76 (dd, J

[0032] = 8.6, 2.3 Hz, 1H), 6.66 (d, J = 2.3 Hz, 1H), 5.38 (s, 1H). The reaction formula is as follows:

[0033] . ...

Embodiment 2

[0041] Embodiment 2: the determination of the fluorescence spectrum of fluorescent probe DCICA and Cys action

[0042] (1) Prepare solution: prepare 2 mM stock solution of fluorescent probe DCICA with dimethyl sulfoxide (DMSO); prepare 2 mM Cys solution with distilled water;

[0043] (2) Add 2 mL of EtOH / PBS buffer solution (v / v = 1 / 1, pH = 7.4) and 10 µL of the fluorescent probe DCICA stock solution into the fluorescence cuvette, and measure the concentration of the probe on a fluorescence spectrophotometer. Fluorescence spectrum (excitation wavelength 510 nm), and then gradually add Cys solution, increase by 5 µL each time, gradually add from 5 µL, and finally add a volume of 50 µL, leave it for 5 minutes after each addition, and record in the fluorescence spectrophotometer The fluorescence spectrum was measured on the surface. After adding Cys, the probe showed a new fluorescence emission peak at 680 nm, and the fluorescence intensity gradually increased with the addition o...

Embodiment 3

[0044] Embodiment 3: the determination of the response time of fluorescent probe DCICA and Cys action

[0045] In the fluorescent cuvette, add 2 mL EtOH / PBS buffer solution (v / v = 1 / 1, pH = 7.4) and 10 µL fluorescent probe DCICA stock solution, then add 5 molar equivalent Cys solution, and measure The fluorescence intensity change of the probe at 680 nm (excitation wavelength 510 nm) was measured on the instrument. As the reaction time prolongs, the fluorescence intensity increases continuously. When the reaction reaches 300 s, the fluorescence intensity is basically constant (see Image 6 ), indicating that the detection method is fast, and the detection can be completed within 5 minutes.

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Abstract

The invention belongs to the technical field of analysis and detection, and provides a lysosome-targeted Cys near-infrared fluorescent probe and a preparation method and application thereof. The near-infrared fluorescent probe is 3-(2-(3-(dicyanomethylene)-5,5-dimethylcyclohexen-1-yl)vinyl)-4-morpholinyl coumarin-7-acrylate which is abbreviated as DCICA. The prepared lysosome-targeted Cys near-infrared fluorescent probe has the characteristics of novel structure, lysosome targeting performance and near-infrared fluorescence emission (wherein an emission wavelength is 680 nm), can realize high-selectivity high-sensitivity detection of a Cys content of a solution, conducts specific detection of Cys in cell lysosome by using a laser confocal imaging technology, is of important guiding significance to research on the molecular mechanism of participation of the Cys in the life activity of the lysosome, and has a wide application prospect.

Description

technical field [0001] The invention belongs to the technical field of analysis and detection, in particular to a lysosome-targeted Cys near-infrared fluorescent probe and a preparation method and application thereof. Background technique [0002] Cysteine ​​(Cys) is a sulfur-containing amino acid necessary for organisms. It exists in almost all cells of mammals and has the physiological functions of maintaining the healthy growth of cells and tissues and delaying aging. Abnormal cysteine ​​levels in the human body can cause adverse symptoms such as slow growth, hair depigmentation, edema, lethargy, liver function damage, loose skin, and physical weakness. Therefore, the detection of Cys with high selectivity and high sensitivity is of great significance for the early diagnosis and treatment of diseases. Among many detection methods of Cys, fluorescence detection method has attracted extensive attention due to its advantages of simple operation, high sensitivity, real-time ...

Claims

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Application Information

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IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06G01N21/6486C09K2211/1007C09K2211/1033C09K2211/1088
Inventor 张永斌张瑜钞建宾郝俊生霍方俊阴彩霞
Owner SHANXI UNIV
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