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Compound for detecting leucine aminopeptidase, preparation method of compound and application of compound

A compound, leucine technology, applied in the field of near-infrared fluorescent molecular probes for detecting leucine aminopeptidase (LAP) and its preparation, which can solve the problems of poor water solubility, lack of stability, and short emission wavelength of probe molecules. problem, to achieve the effect of high sensitivity, strong anti-interference ability and good selectivity

Active Publication Date: 2019-03-08
HUBEI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, many of them have defects such as poor water solubility, short emission wavelength and lack of stability.

Method used

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  • Compound for detecting leucine aminopeptidase, preparation method of compound and application of compound
  • Compound for detecting leucine aminopeptidase, preparation method of compound and application of compound
  • Compound for detecting leucine aminopeptidase, preparation method of compound and application of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0051] Example: Preparation method of near-infrared fluorescent molecular probe NF-O-Leu.

[0052] The compound NF-OH (32.0 mg, 0.077 mmol), Fmoc-Leu-Br (160.2 mg, 0.308 mmol), KHCO 3 (20.6 mg, 0.15 mmol), 18-crown-6 (40.4 mg, 0.15 mmol) and KI (85.2 mg, 0.385 mmol) were mixed in 10.0 mL of acetone, and the reaction system was stirred at 40 ℃ for 10 hours under nitrogen protection. After removing the solvent, the residue was added to a solution of 5% piperidine (by volume) in N,N-dimethylformamide, and stirring was continued at room temperature for 4-6 hours. Then it was extracted with dichloromethane, and the organic phases were combined, dried over anhydrous sodium sulfate, and subjected to column chromatography to obtain the product: NF-O-Leu.

[0053] The hydrogen spectrum of the compound NF-O-Leu (such as Figure 4a ), the deuterated reagent is d 6 -CD 3 OD.

[0054] 1 H NMR (400 MHz, CD 3 OD): δ 8.04-8.01 (m, 1H), δ 7.77-7.75 (d, 1H), δ7.44-7.43 (d, 1H), δ 7.39-7...

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Abstract

The invention belongs to the field of biochemical engineering, and particularly relates to a preparation method and an application of a near-infrared fluorescent molecular probe NF-O-Leu for detectingleucine aminopeptidase (LAP). The structural general formula of the compound NF-O-Leu is as shown in the specification, R1, R2, R3, R4, R5 and R6 are introduced substituent groups and can be used foradjusting electronic effects of the fluorescent probe, so that fluorescence of the fluorescent probe is changed. According to the near-infrared fluorescent molecular probe NF-O-Leu, near-infrared fluorescent dyes NF-OH and LAP receptor units (leucine residues) are bridged together by para-aminobenzoic acid (PABA), the target near-infrared fluorescent molecular probe NF-O-Leu is synthesized and used for specifically monitoring LAP activity in vitro and in vivo, and trace LAP in living cells is successfully tracked and detected.

Description

technical field [0001] The invention belongs to the field of biochemical industry, and relates to the construction of a near-infrared fluorescent molecular probe for detecting intracellular leucine aminopeptidase (LAP), in particular to a near-infrared fluorescent molecular probe for detecting leucine aminopeptidase (LAP). Fluorescent molecular probes and their preparation methods and biological applications. Background technique [0002] Leucine aminopeptidase (LAP), as one of the important exopeptidases that catalyze the hydrolysis of N-terminal leucine residues of proteins or peptides, plays a very important role and affects various physiological and pathological processes of organisms . The abnormal content of LAP in human tissues is often associated with various diseases, such as epithelial ovarian cancer and breast cancer, making LAP an important cancer-related biomarker. Therefore, developing an effective method for monitoring LAP in biological systems will provide ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12C09K11/06G01N21/64
CPCG01N21/6428C09K11/06C07D209/12C09K2211/1033C09K2211/1029C09K2211/1011C09K2211/1007
Inventor 王飞翼杨桂春柴云陈祖兴卢翠芬聂俊琦马超
Owner HUBEI UNIV
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