Amyloid protein-labeled fluorescence probes, and making method and application thereof

A fluorescent probe and reaction technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effect of biological activity advantages

Inactive Publication Date: 2018-05-22
KUNMING MEDICAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The 1,8-naphthyridine group has good biological activity and is sought after by scientific and technological workers in the design and synthesis of drug molecu...

Method used

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  • Amyloid protein-labeled fluorescence probes, and making method and application thereof
  • Amyloid protein-labeled fluorescence probes, and making method and application thereof
  • Amyloid protein-labeled fluorescence probes, and making method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1C3

[0049] The preparation of embodiment 1C3 compound

[0050] according to figure 2 The synthetic scheme shown prepares the C3 compound.

[0051] step 1:

[0052] Synthesis of 2-amino-5,7-trifluoromethyl-1,8-naphthyridine (compound 1): 2,6-diaminopyridine (commercially available, analytically pure, 10.9g, 0.1mol) and hexafluoroacetyl Acetone (commercially available, analytically pure, 10.0 g, 0.1 mol), 100 mL of phosphoric acid, under nitrogen protection, stirred and refluxed for 24 hours. The reaction solution was cooled, and adjusted to neutrality with ammonia water under ice bath conditions. Refrigerate overnight at 5°C, then filter with suction, wash the filter cake with cold water, and dry to obtain the crude product. The crude product was recrystallized from absolute ethanol to obtain light yellow solid powder. Yield: 17.3g (61.3%).

[0053] Step 2:

[0054] Synthesis of Compound 3: Compound 1 (2.81 g, 0.01 mol) and Compound 2 (0.01 mol) were dissolved in 100 mL of an...

Embodiment 2

[0061] Example 2 Compound C3 is used for amyloid Aβ 42 , Aβ 40 fluorescent label

[0062] 1. Amyloid Aβ 42 , Aβ 40 Preparation of Polymers: Human Amyloid Amyloid Aβ 42 (AS-20276, purified by HPLC, AnaSpec Co.), Aβ 40 (AS-24236, purified by HPLC, AnaSpec Co.) 1mg was dissolved in 4mL PBS buffer solution (pH=7.4), the protein concentration was 0.25mg / mL, continued to shake gently, incubated at 37°C for 42h, added PBS buffer solution to dilute 0.2 mg / mL;

[0063] 2. Compound C3 ethanol solution (1 μmol, spectrum pure) 300 μL, add Aβ 42 polymer or Aβ 40 Polymer or BSA (bovine serum albumin, 0.2mg / mL, PBS buffer solution) 300μL, then add PBS buffer solution 2400μL, the total solution volume is 3000μL, the total protein is 60μg, the preparation ratio is compound C3: protein 1:1, The mixture was incubated at room temperature for 30 min;

[0064] 3. Fluorescence detection after incubation, fluorescence instrument F-4600FL Spectrophotometer, EX WL: 350nm.

[0065] Figure 5 ...

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Abstract

The invention belongs to the field of biomedicines, and concretely relates to amyloid protein-labeled fluorescence probes, and a making method and an application thereof. The fluorescence probes are compounds represented by formula I, and R1 and R2 in the formula I are independently selected from -CF3 and -CN. The invention also relates to the application of the compounds of formula I in amyloid protein labeling as the fluorescence probes. The compounds of formula I can be used for preparing products for diagnosing the Alzheimer's disease. BODIPY fluorescence probe molecules containing a bioactive 1,8-naphthyridyl group as a parent compound are synthesized for the first time, can be applied to beta-amyloid protein labeling, and can be used for the early stage diagnosis of the Alzheimer's disease.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to a fluorescent probe for marking amyloid and its preparation method and application. Background technique [0002] Alzheimer's disease (AD) is a neurodegenerative disease that affects millions of people worldwide and remains difficult to diagnose and incurable. Current clinical drugs can only improve the symptoms of AD patients and slow down the onset of AD disease, but cannot fundamentally treat it. A large number of studies have shown that pathological changes in the brain have occurred as early as 10-20 years before the appearance of AD symptoms. There are currently three hypotheses for the pathological mechanism of AD: amyloid deposition, neurofibrillary tangles, and cholinergic neuron degeneration. Among them, "amyloid deposition" is widely recognized. In the early stage of AD, β-amyloid (Aβ, mainly Aβ40 and Aβ42, the neurotoxicity of Aβ42 is stronger than Aβ40) grad...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1096G01N21/6486
Inventor 李慧方洁周勇迟绍明李琮
Owner KUNMING MEDICAL UNIVERSITY
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