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Photochromic monomer, its preparation method, amphiphilic polymer, its preparation method and vesicle and its application

An amphoteric polymer, photochromic technology, applied in the field of cells, can solve the problems of irreversibility and regulation of photolysis, and achieve the effect of controllable regulation and improvement of permeability

Active Publication Date: 2017-12-22
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the irreversible photolysis reaction of the above method, the vesicle permeability can only be changed from low to high permeability, and cannot be further regulated in turn.

Method used

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  • Photochromic monomer, its preparation method, amphiphilic polymer, its preparation method and vesicle and its application
  • Photochromic monomer, its preparation method, amphiphilic polymer, its preparation method and vesicle and its application
  • Photochromic monomer, its preparation method, amphiphilic polymer, its preparation method and vesicle and its application

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preparation example Construction

[0098] The present application also provides a preparation method of the photochromic monomer, comprising the following steps:

[0099] reacting the compound having the structure of formula (III) and the compound having the structure of formula (IV) in a solvent under the action of a catalyst to obtain a photochromic monomer;

[0100]

[0101] Among them, R 1 is H or MeO;

[0102] R 2 for NO 2 or CN;

[0103] R 3 for H or CH 3 ;

[0104] n is 1-11.

[0105] The photochromic monomer described in the present application is obtained by reacting the hydroxyl group in the compound of formula (III) with the isocyanate group of the compound of formula (IV).

[0106] In the above process of preparing the photochromic monomer, the solvent is preferably dichloromethane, and the catalyst is preferably dibutyltin dilaurate.

[0107] According to the present invention, after synthesizing the photochromic monomer, use it as the hydrophobic segment of the polymer, and polymerize ...

Embodiment 1

[0167] Dissolve 1 molar equivalent of the hydroxyethyl-functionalized photochromic molecular precursor represented by formula (VII) in 30 mL of dry dichloromethane, add 0.5% DBTL as a catalyst, Add 1.5 molar equivalents of isocyanoethyl methacrylate represented by formula (Ⅷ), stir and react for 7 to 24 hours, wash with saturated brine twice after the reaction, add anhydrous MgSO 4 Dry, remove the solvent by rotary evaporation under reduced pressure, separate and purify by column chromatography using dichloromethane-ethyl acetate as eluent to obtain the corresponding product, which is denoted as M1 monomer, and its yield is 75-92%. The structure of the M1 monomer was characterized by H NMR, C NMR and high-resolution mass spectrometry, and the results showed that Figure 1~3 shown.

[0168]

[0169] In the above formula, R 1 for H, R 2 for NO 2 , R 3 is H, n is 1.

Embodiment 2

[0171] 1.2g of M1 monomer, 0.3g of PEG-CTA chain transfer agent shown in formula (IX) and 5.0mg of AIBN initiator were dissolved in 4mL of dioxane, then added to a sealed tube containing a magnetic stirrer, fully removed Seal the tube after gas, place it in an oil bath at 70°C, stop the reaction after 7-12 hours of polymerization, and precipitate in anhydrous ether, precipitate three times, and dry in a vacuum oven to obtain polymer P1. Figure 4 NMR characterization of polymer P1.

[0172]

[0173] Among them, R 1 for H, R 2 for NO 2 , R 3 is H, x is 19, n is 1, and m is 45.

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Abstract

The invention provides a photochromic monomer and a preparation method thereof. The invention also provides an amphiphilic polymer with the photochromic monomer as a hydrophobic chain section and a preparation method thereof. The invention also provides a vesicle obtained by self-assembling of the amphiphilic polymer. The photochromic monomer elements are distributed in a hydrophobic double layer coating of the vesicle, and the photochromic monomer element as a polymer hydrophobic chain section undergoes a reversible ring opening-closing reaction under extraneous wavelength selective illumination stimulation so that vesicle permeability reversible adjustment is realized and the vesicle structure is not changed.

Description

technical field [0001] The invention relates to the field of cell technology, in particular to a photochromic monomer, a preparation method thereof, an amphiphilic polymer, a preparation method thereof, vesicles and applications thereof. Background technique [0002] Cells are the basic unit of life. A cell is composed of a cell membrane and various organelles and cytoplasmic matrix wrapped inside it. Cells need to grow and differentiate, and also need to complete various signal transmission and communication between cells. Each cell coordinates with each other to complete a complex life process, and all of these require controllable material transmission inside and outside the cell membrane. As we all know, the cell membrane is formed by the assembly of phospholipid molecules composed of hydrophobic alkyl chains and polar hydrophilic heads, and the hydrophobic alkyl chains stack each other to form a hydrophobic bilayer membrane, so water-soluble substances inside and outsi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C08F222/22C08F261/10C08F2/38B01J19/00A61K9/127A61K41/00A61K47/34
CPCA61K9/1273A61K41/0042A61K47/32B01J19/0093C07D491/107C08F2/38C08F261/10C08F222/22
Inventor 刘世勇汪枭睿
Owner UNIV OF SCI & TECH OF CHINA
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