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A kind of aggregation-induced luminescent peptide micellar diagnostic reagent and its application in near-infrared region bioimaging

A technology of aggregation-induced luminescence and diagnostic reagents, which can be used in preparations, peptides, and drug delivery for in vivo experiments. Diversified properties and functions, high yield, and simple synthesis

Active Publication Date: 2022-05-17
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis process of AIEgen molecules reacting with polymers is complicated, and it is easy to introduce organic reagents, which reduces its biological safety, and the molecules themselves lack tumor targeting, so long-term high-efficiency and low-toxicity tracers cannot be carried out.

Method used

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  • A kind of aggregation-induced luminescent peptide micellar diagnostic reagent and its application in near-infrared region bioimaging
  • A kind of aggregation-induced luminescent peptide micellar diagnostic reagent and its application in near-infrared region bioimaging
  • A kind of aggregation-induced luminescent peptide micellar diagnostic reagent and its application in near-infrared region bioimaging

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Experimental program
Comparison scheme
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Embodiment 1

[0057] The synthesis of embodiment one, ACBT

[0058] Synthesize ACBT according to the following synthetic route:

[0059]

[0060] The synthesis steps of ACBT are:

[0061] 7-bromobenzo[c][1,2,5]thiadiazole-4-carbaldehyde (abbreviated as ABB) (1mmol), 4-triphenylamine borate (2mmol), anhydrous sodium carbonate (1.06g, 10mmol ), tetrakis(triphenylphosphine)palladium (50mg, 0.04mmol) was put into a three-necked flask, and nitrogen gas was fed to remove the oxygen in the flask. Then, 20 mL of toluene and 3 mL of water were injected into the flask under a nitrogen atmosphere, and the flask was placed in an oil bath at 110° C. for reflux reaction for 24 h. After the reaction, 40 mL of dichloromethane and 4.0 g of silica gel powder were added, and spun into powder using a rotary evaporator. Compound 1 (abbreviated as ABT) was purified by silica gel column chromatography, using a mixed solvent of dichloromethane and petroleum ether with a volume ratio of 3:1 as the eluent, and...

Embodiment 2

[0064] Example 2. Synthesis of aggregation-induced luminescent polypeptide micellar diagnostic reagent AGPR

[0065] 1. The functional chimeric peptide GGFLG-PEG was synthesized by the standard Fmoc solid-phase peptide synthesis method 8 -R 8GD: Weigh 2-chloro-trityl chloride resin (0.8g, 0.97mmol / g) into the peptide solid-phase synthesis column, add 20 mL N,N-dimethylformamide (DMF) to soak the resin for 30 minutes, Make it fully swell and remove DMF by suction filtration. Prepare to insert the first amino acid and enter the amino acid condensation reaction. Then, a DMF solution in which Fmoc-Asp(OtBu)-OH (3 times the degree of substitution of the resin) and DIEA (6 equivalents of the degree of substitution of the resin) was dissolved was added to the polypeptide solid-phase synthesis column, and reacted for 2 hours. After the reaction, the filtrate was sucked away and washed 4 times with DMF. The peptide resin after condensation of the first amino acid protected by FMOC ...

Embodiment 3

[0069] Example 3. Self-assembly performance and morphology characterization of aggregation-induced luminescent polypeptide micellar diagnostic reagent AGPR

[0070] Using pyrene as a hydrophobic fluorescent probe, the critical micelle concentration (CMC) value of AGPR was measured by fluorescence spectrophotometer to evaluate the self-assembly performance and stability of AGPR. Accurately weigh 9.7 mg of hydrophobic pyrene fluorescent molecule, dissolve it in 10 mL of acetone, and then dilute to 4.6 × 10 -6 mol / L, spare. Into 3.6mL AGPR aqueous solution (take the ACBT-GGFLG-PEG prepared in step 2 of Example 2) that has prepared a series of concentrations 8 -R 8 GD powder was dissolved in deionized water) Add 45μL 4.6×10 -6 mol / L pyrene solution in acetone, configured as a sample. Place the prepared sample in a shaker (150r / min) at 37°C for 24 hours to ensure that the acetone is completely volatilized. Finally, the emission spectrum of the sample solution within 360-400 n...

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Abstract

The invention belongs to the technical field of preparation of antitumor drugs, and specifically discloses a polypeptide micellar diagnostic reagent AGPR with aggregation-induced emission (AIE) properties and its application in near-infrared region biological imaging. The diagnostic reagent AGPR is composed of amphiphilic small molecule functional peptide ACBT-GGFLG-PEG n -R 8 GD, 4≤n≤20, spherical peptide micelles formed by self-assembly in aqueous solution. The novel AIEgen compound ACBT designed and synthesized by the present invention is a linear D-A-A molecule, and its emission peak is located in the near-infrared region. The present invention further uses the multifunctional chimeric peptide GGFLG-PEG 8 -R 8 GD modified the ACBT molecule to achieve high-efficiency enrichment of AIEgen molecule (ACBT) in tumor sites, and significantly enhanced fluorescence intensity in Cathepsin B-rich cell lysosomes / endosomes, with excellent imaging effects, so it is expected Applied to specific tracking of tumor cells.

Description

technical field [0001] The invention belongs to the technical field of anti-tumor drug preparation, and specifically relates to a polypeptide micelle-type diagnostic reagent AGPR with aggregation-induced emission (AIE) properties and its application in near-infrared region biological imaging. Background technique [0002] For a long time, fluorescent materials have provided important application value in the fields of biological imaging, molecular recognition and tracing, environmental detection and protection, and medical diagnosis. Existing fluorescent tracer reagents (such as fluorescent proteins, quantum dots, luciferase and organic fluorescent molecular dyes, etc.) have many problems, among which luciferase and fluorescent proteins need gene transfection, resulting in the normal physiological function of cells will be affected. Interference; quantum dots are toxic to heavy metals, and their fluorescence intensity will drop sharply during cell differentiation; traditiona...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/08G01N21/64A61K49/00
CPCC07K7/08G01N21/6402A61K49/0021A61K49/0056A61K49/0054A61K49/0082
Inventor 程崟家秦四勇张爱清
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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