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Hydrogen peroxide responsive polymer nano-carrier with fluorescence ratio characteristic as well as preparation method and application thereof

A hydrogen peroxide and nanocarrier technology, applied in the field of hydrogen peroxide responsive synthetic polymers, can solve the problems of reduced treatment results, multidrug resistance, low solubility, etc.

Inactive Publication Date: 2020-10-23
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, current chemotherapy generally has difficulties such as low solubility, poor biodistribution and pharmacokinetics, failure to target, possible multidrug resistance in special types of tumors, inherent cell barriers, and inefficient cellular uptake. significantly reduced the outcome of the treatment

Method used

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  • Hydrogen peroxide responsive polymer nano-carrier with fluorescence ratio characteristic as well as preparation method and application thereof
  • Hydrogen peroxide responsive polymer nano-carrier with fluorescence ratio characteristic as well as preparation method and application thereof
  • Hydrogen peroxide responsive polymer nano-carrier with fluorescence ratio characteristic as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0109] Implementation Example 1: Preparation of Pentafluorophenol Isonitrile Monomer

[0110] Add p-nitrobenzoic acid (1.1eq), pentafluorophenol (1eq), EDCI (1.2eq), and DMAP (0.5eq) into a two-necked flask, use dichloromethane as a solvent, and react at room temperature. After the reaction is followed by TLC, use Wash 3 times with water, 3 times with saturated sodium bicarbonate solution, 3 times with saturated sodium chloride solution, collect the organic phase, add anhydrous sodium sulfate to dry for 3 hours, remove anhydrous sodium sulfate by suction filtration, remove the solvent by rotary evaporation, pass through a silica gel column After purification (eluent: petroleum ether: ethyl acetate = 1:1), the product was collected, the solvent was removed, and vacuum-dried to constant weight. After passing through a silica gel column (DCM:PE=1:1), the product was collected, spin-dried and then vacuum-dried to constant weight to obtain product I, the structural formula of which...

Embodiment 2

[0120] Implementation Example 2: Preparation of Benzene Isonitrile Monomer with Hydrogen Peroxide Response

[0121] Add pentafluorophenol isonitrile (1eq), 4-hydroxymethylphenylboronic acid pinacol ester (1.1eq), DMAP (1.2eq), and anhydrous THF into a two-necked bottle, vacuum-fill with nitrogen, repeat 3 times , under a nitrogen atmosphere, stirred at 30°C for reaction, followed by TLC and spin-dried after the completion of the reaction, passed through a silica gel column (DCM:PE=9:1), collected the product, spin-dried, vacuum-dried to constant weight, and stored in a freezer. The synthetic route is as follows:

[0122]

Embodiment 3

[0123] Implementation Example 3: Preparation of tetraphenylethylene benzene isocyanate monomer

[0124] Add zinc powder (4.2eq), 4-hydroxybenzophenone (1eq), and diphenylketone (1eq) into the two-necked bottle, and make the two-necked bottle pass through the N 2 Degas for 30 min, then add anhydrous THF as solvent, cool the mixture to -20 °C, slowly inject TiCl 4 (2eq). The mixture was stirred at -20°C for 0.5 hours, then refluxed at 55°C overnight. After passing K 2 CO 3 Aqueous solution (10%) quenched the reaction, and extracted with ether, combined the organic phases and washed three times with brine, and the mixture was washed with anhydrous Na 2 SO 4 Dry, pass through a silica gel column (DCM:petroleum ether=4:1), collect the product, remove the solvent, spin dry and vacuum-dry to constant weight to obtain product I, the structural formula is:

[0125]

[0126] Add 4-nitrobenzoic acid (2.2eq), EDCI (2.2eq), DMAP (1eq) into a two-necked flask, anhydrous CH 2 Cl 2...

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PUM

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Abstract

The invention relates to a hydrogen peroxide responsive polymer nano-carrier with a fluorescence ratio characteristic. The nano-carrier is of a spherical micelle structure, and is formed by self-assembling of an amphiphilic block copolymer with hydrogen peroxide responsiveness and ratiometric fluorescence imaging characteristics. The structural formula of the amphiphilic block copolymer having hydrogen peroxide responsiveness and ratiometric fluorescence imaging characteristics is as follows: R1 is a group having hydrogen peroxide responsiveness; R2 is a group with an aggregation-induced emission effect; R3 is a PEG hydrophilic chain; and R5 is a group with strong positive charges. The nano-carrier disclosed by the invention can be used for loading, transporting and program releasing of hydrophobic dye molecules and drug molecules as well as cell imaging and fluorescent molecular probes.

Description

technical field [0001] The present invention mainly relates to the field of polymer reaction, in particular to the preparation and application of a hydrogen peroxide-responsive synthetic polymer with fluorescence ratio characteristics. Background technique [0002] my country's contemporary medical level has been greatly improved, but the treatment of cancer, the main disease that endangers human health and even causes death, is still difficult, and the incidence rate is still increasing year by year. The most widely used means are chemotherapy, surgery and radiotherapy. Among them, surgery and radiotherapy are local treatments, which are only effective for tumors at the treatment site, and are difficult to effectively treat potential metastatic lesions and cancers that have already undergone clinical metastasis. Chemotherapy can treat and suppress primary lesions, metastatic lesions, and subclinical metastatic lesions, but there are also some unsatisfactory aspects. For e...

Claims

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Application Information

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IPC IPC(8): A61K49/00A61K9/107A61K47/34A61P35/00C08G61/02
CPCA61K9/1075A61K47/34A61K49/0054A61K49/0082A61K49/0021A61P35/00C08G61/02C08G2261/126
Inventor 殷俊谢开云李晖童犇刘诗云王宇泽
Owner HEFEI UNIV OF TECH
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