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A ratiometric leucine aminopeptidase fluorescent probe, its preparation method and its application in targeted imaging of liver tumor cells

A leucine aminopeptidase, fluorescent probe technology, applied in fluorescence/phosphorescence, preparation of sugar derivatives, organic chemical methods, etc., to achieve good imaging effects and good water solubility

Active Publication Date: 2022-02-25
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the accurate detection of LAP activity in liver tumor cells still needs to solve the problem of the targeting of fluorescent probes to liver tumor cells. At present, there are no reports on LAP fluorescent probes with the ability to target liver tumor cells.

Method used

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  • A ratiometric leucine aminopeptidase fluorescent probe, its preparation method and its application in targeted imaging of liver tumor cells
  • A ratiometric leucine aminopeptidase fluorescent probe, its preparation method and its application in targeted imaging of liver tumor cells
  • A ratiometric leucine aminopeptidase fluorescent probe, its preparation method and its application in targeted imaging of liver tumor cells

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: Preparation of Compound II

[0020]

[0021] The compounds shown in Formula I were 0.1 mmol, Fmoc-Leu-OH 0.15 mmol, diisopropylamine 0.15 mmol, 1-ethyl-(3-dimethylaminopropyl) carbonoyl diimide 0.15 mmol, 1-hydroxybenzene triazole 0.15 mmol is added to a dichloromethane and a DMF mixed solution 100 mL (volume ratio 1: 1), nitrogen protection, stirring, 25 ° C for 24 h, after the end, remove the reaction solvent, crude product Chromatography was separated, dichloromethane: methanol was 10: 1 as a mobile phase, resulting in a compound of formula II 380 mg.

[0022] 1 H NMR (400 MHz, DMSO) δ8.93 (DD, J = 8.6, 1.3 Hz, 1H), 8.78 (DD, J = 4.0, 1.5 Hz, 1H), 8.54 (S, 1H), 7.88 (D, J = 7.5Hz, 2H), 7.79 (D, J = 7.8 Hz, 1H), 7.70 (DD, J = 7.4, 3.0 Hz, 2H), 7.61 (D, J = 8.0 Hz, 1H), 7.54 (DD, J = 8.6, 4.1Hz, 1H), 7.41 (t, j = 7.4 Hz, 2H), 7.31 (t, j = 7.1 Hz, 2H), 7.27-7.23 (m, 1H), 7.20-7.11 (m, 1H), 6.94 (D, J = 8.0 Hz, 1H), 6.20 (S, 2H), 5.76 (S, 2H), 5.60 (D, J = 9.2 H...

Embodiment 2

[0023] Example 2: Preparation of Compound II

[0024]

[0025] The compounds shown in Formula I were 0.1 mmol, Fmoc-Leu-OH 0.12 mmol, diisopropylamine 0.12 mmol, 1-ethyl-(3-dimethylaminopropyl) carbonoyl diimide 0.12 mmol, 1-hydroxybenzene triazole 0.12 mmol was added to dichloromethane and a DMF mixed solution 100 mL (volume ratio 1: 1), nitrogen gas protection, stirring, 25 h back at 25 ° C, after completion, remove the reaction solvent, crude product Chromatography was separated, dichloromethane: methanol was 10: 1 as a mobile phase, resulting in the compound of formula II 396 mg.

Embodiment 3

[0026] Example 3: Preparation of Compound III

[0027]

[0028] 0.5 mmol of the compound of Compound II, 0.5 mmol of dimette tetrahydrofuran solution was added to 30 ml of dichloromethane solution, 50 ° C reaction for 1 h, after the reaction, the reaction solvent was removed under reduced pressure, and the crude product was separated by column chloride. Methane: methanol is 8: 1 is a mobile phase, resulting in a compound of formula III, 320 mg.

[0029] 1 H NMR (400MHz, DMSO) δ8.95 (D, J = 8.6Hz, 1H), 8.80 (D, J = 2.8 Hz, 1H), 8.57 (S, 1H), 8.37 (S, 2H), 7.63 (D , J = 8.0Hz, 1H), 7.57 (DD, J = 8.6, 4.96 (D, J = 8.0 Hz, 1H), 5.62 (D, J = 9.2Hz, 1H), 4.50 (DD J = 11.5, 8.7 Hz, 2H), 4.20-1.16 (m, 4H), 3.97 (S, 2H), 3.86 (D, J = 2.8 Hz, 1H), 3.68 (DD, J = 9.4, 3.1 Hz, 1H), 1.79 (D, J = 18.1 Hz, 1H), 1.60-1.41 (m, 2H), 0.75 (DD, J = 18.8, 6.3 Hz, 6H). 13 C NMR (101MHz, DMSO) δ170.50,147.42,146.56,145.83,137.60,134.42,128.81,126.44,122.28,121.48,114.36,108.90,88.49,75.37,73.67,69.52,6...

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Abstract

The invention discloses a ratio-type leucine aminopeptidase fluorescent probe, a preparation method thereof and an application thereof in targeted imaging of liver tumor cells. The structural formula of the ratiometric leucine aminopeptidase fluorescent probe is shown in formula III: the ratiometric leucine aminopeptidase fluorescent probe has high fluorescence quantum yield, obvious ratiometric characteristics, and can be realized in liver tumor cells. Targeted imaging and other advantages. The fluorescent probe has been successfully applied to the targeted imaging of leucine aminopeptidase in liver tumor cells, and achieved good application results.

Description

Technical field [0001] The present invention relates to the field of fluorescent probe biological applications, and more particularly to a ratio of leucine aminopeptidase fluorescence probes having a targeted capability of hepatoma cells and a preparation method thereof and its application in hepatoma cells. . Background technique [0002] Liver cancer is one of the common malignant tumors. It has the characteristics of an early symptoms of condition, and the development of the disease is rapid, and the early and accurate diagnosis can effectively improve the cure rate. The leucine aminopeptidase (LAP) is an important liver tumor marker, which is widely distributed in human tissue, and its activity changes are closely related to the growth, split and migration of liver tumor cells. At present, there is one of the reference indicators of leucine aminopeptidase activity in the blood in the blood. However, it is subject to non-in-situ detection to obtain accurate data of LAP activit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/056C07H1/00C09K11/06G01N21/64
CPCC07H19/056C07H1/00C09K11/06G01N21/6428G01N21/6486C07B2200/07C09K2211/1029C09K2211/1059C09K2211/1088
Inventor 杜奎盛力沈润溥刘健丰诚杰
Owner SHAOXING UNIVERSITY
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