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Fluorescent small molecule as well as preparation method and application thereof

A small molecule, fluorescent technology, applied in the fields of applications, chemical instruments and methods, luminescent materials, etc., can solve the problems of reducing the concentration of F127 and the adverse effects of loaded cell growth and migration

Pending Publication Date: 2022-05-27
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

High solid content of F127 will also have adverse effects on the growth and migration of loaded cells
How to reduce the concentration of F127 and have reversible temperature sensitivity is a challenging problem

Method used

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  • Fluorescent small molecule as well as preparation method and application thereof
  • Fluorescent small molecule as well as preparation method and application thereof
  • Fluorescent small molecule as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] Step 1: Synthesis of Small Molecule A:

[0081] Step 1.1, synthesis of compound 1: 1.0 g of 4-bromo-1,8-naphthalene anhydride and 0.35 g of ammonia water were added to 8 ml of absolute ethanol, heated to boiling and stirred overnight. After the reaction was completed, it was cooled to room temperature, and the reaction solution was poured into 40 ml of ice water and filtered to obtain a brown solid. The dried solid was recrystallized with an appropriate amount of acetic acid to obtain pure compound 1 with a yield of 88%.

[0082] Step 1.2, the synthesis of compound 2: 0.5 g of compound 1 and 3.2 mL of ethylenediamine were dissolved in 7.6 mL of methoxymethanol, then 50 mg of copper sulfate pentahydrate was added, and the mixture was heated to boiling and stirred overnight. After cooling to room temperature, the reaction solution was poured into 100 ml of water and filtered to obtain a yellow solid. The dried solid was recrystallized from ethanol to obtain pure compound ...

Embodiment 2

[0095] Step 1: Synthesis of Small Molecule A:

[0096] Step 1.1, synthesis of compound 1: 4-Bromo-1,8-naphthalene anhydride (1.35 g, 5 mmol) and ammonia water (2.5 ml) were added to 150 ml of ethanol solution, heated to boiling and stirred overnight. After the reaction was completed, it was cooled to room temperature, and the reaction solution was filtered and rinsed with ethanol to obtain a brown solid. The dried solid was recrystallized with an appropriate amount of acetic acid to obtain pure compound 1 with a yield of 87%.

[0097]Step 1.2, the synthesis of compound 2: 0.5 g of compound 1 and 3.2 mL of ethylenediamine were dissolved in 7.6 mL of methoxymethanol, then 50 mg of copper sulfate pentahydrate was added, and the mixture was heated to boiling and stirred overnight. After cooling to room temperature, the reaction solution was poured into 100 ml of water and filtered to obtain a yellow solid. The dried solid was recrystallized from ethanol to obtain pure compound 2 w...

Embodiment 3

[0111] Step 1: Synthesis of Small Molecule B:

[0112] Step 1.1, synthesis of compound 1: 1.0 g of 4-bromo-1,8-naphthalene anhydride and 0.35 g of n-butylamine were added to 8 ml of acetic acid solution, heated to boiling and stirred overnight. After the reaction was completed, it was cooled to room temperature, and the reaction solution was poured into 40 ml of ice water and filtered to obtain a brown solid. The dried solid was recrystallized with an appropriate amount of acetic acid to obtain pure compound 1 with a yield of 85%.

[0113] Step 1.2, the synthesis of compound 2: 0.5 g of compound 1 and 3.2 mL of ethylenediamine were dissolved in 7.6 mL of methoxymethanol, then 50 mg of copper sulfate pentahydrate was added, and the mixture was heated to boiling and stirred overnight. After cooling to room temperature, the reaction solution was poured into 100 ml of water and filtered to obtain a yellow solid. The dried solid was recrystallized from ethanol to obtain pure compou...

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PUM

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Abstract

The invention discloses a fluorescent small molecule as well as a preparation method and application thereof, the fluorescent small molecule has a structural formula as shown in a formula I. In the formula I, R1 is independently selected from one of H and C1-C12 alkyl groups; and R2 is independently selected from one of C2-C10 alkyl groups. The sol-gel transition temperature of the reversible temperature-sensitive fluorescent hydrogel provided by the invention can be adjusted between 30 DEG C and 40 DEG C, and the temperature is close to the physiological temperature in a human body, so that the reversible temperature-sensitive fluorescent hydrogel is particularly suitable for the field of biological medicines.

Description

technical field [0001] The patent of the present invention relates to the field of biological material preparation, in particular to the preparation of a fluorescent small molecule and its preparation method and application. Background technique [0002] "Hydrogel" scaffolds are similar to the extracellular matrix structure of organisms, which can provide a good environment for cells to obtain nutrients, growth and metabolism during tissue healing, and have the functions of promoting healthy tissue growth and accelerating wound healing, making them ideal Injectable or 3D printable bioinks. Since both in vivo physiological temperature and in vitro cell culture are in a nutrient solution environment with a temperature of 37 °C, thermosensitive hydrogel inks with the lowest critical transition temperature are a simple way to achieve injectable 3D bioprinting. At present, biocompatible reversible thermosensitive hydrogels mainly include: block copolymers such as Pluronic F127 a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06C08F283/06C08F220/60C09D11/30A61K49/00
CPCC07D221/14C09K11/06C08F283/065C09D11/30A61K49/0021A61K49/0073C09K2211/1029C08F220/603Y02B20/00
Inventor 张华周扬陈静徐亚文
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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