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Amphiphilic segmented copolymers, nanoparticles containing amphiphilic segmented copolymers, preparation method of amphiphilic segmented copolymers and use of nanoparticles

A technology of amphiphilic blocks and nanoparticles, which is applied in biochemical equipment and methods, microbial measurement/inspection, preparations for in vivo tests, etc., can solve the problems of short residence time and achieve narrow emission peaks and low emission peaks. Effect of cytotoxicity and low raw material cost

Active Publication Date: 2015-08-05
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Currently used in clinical magnetic resonance imaging diagnosis of T 1 The contrast agent is mainly a complex of gadolinium, but it has a short residence time in the blood circulation and will be quickly excreted from the body, which requires a relatively high injection volume and injection frequency to achieve the desired imaging effect

Method used

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  • Amphiphilic segmented copolymers, nanoparticles containing amphiphilic segmented copolymers, preparation method of amphiphilic segmented copolymers and use of nanoparticles
  • Amphiphilic segmented copolymers, nanoparticles containing amphiphilic segmented copolymers, preparation method of amphiphilic segmented copolymers and use of nanoparticles
  • Amphiphilic segmented copolymers, nanoparticles containing amphiphilic segmented copolymers, preparation method of amphiphilic segmented copolymers and use of nanoparticles

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] 1.41g of 4-(3-oxo-3-phenylpropionyl)phenyl methacrylate (DKMA) (CAS: 157174-85-1), 4.15mg of chain transfer agent dithiobenzoic acid-2- Add phenylpropan-2-ester (CDB) (CAS:201611-77-0), 0.826mg AIBN, 10mL anisole into the reaction flask, the molar ratio of DKMA, AIBN and CDB is 300:0.33:1, 70℃ The reaction was carried out for 12 hours, dissolved and precipitated in 100 mL of ether for 3 times to remove small molecular monomers, and vacuum-dried to obtain polymethacrylic acid-4-(3-oxo-3-phenylpropionyl)phenyl ester (PDKMA). The yield was 50%, NMR calculated degree of polymerization is 152, SEC number average molecular weight is 33.8kDa, molecular weight distribution is 1.28.

[0063] Add 1.810 g of oligoethylene glycol methacrylate (OEGMA), 0.564 mg of PDKMA, 1.519 mg of AIBN and 5 mL of anisole into the reaction flask, the molar ratio of PDKMA, AIBN and OEGMA is 1:0.33:130, 60 °C After the reaction was completed, 200 mL of ether was precipitated three times to remove t...

Embodiment 2

[0072] 1.2g of 4-(3-oxo-3-phenylpropionyl)phenyl acrylate (DKA), 5.55mg of chain transfer agent-2-phenylpropan-2-dithiobenzoate (CDB), Add 0.744mg AIBN and 5mL anisole into the reaction flask, the molar ratio of DKA, AIBN and CDB is 200:0.33:1, react at 70°C for 24 hours, dissolve and precipitate in 200mL ether three times to remove small molecular monomers, and dry in vacuum Obtain polyacrylic acid-4-(3-oxo-3-phenylpropionyl)phenyl ester (PDKA), the yield is 20%, the NMR calculation degree of polymerization is 51, the SEC number average molecular weight is 15.8kDa, and the molecular weight distribution is 1.30 .

[0073] Add 0.8 g oligoethylene glycol methacrylate (OEGMA), 0.24 g PDKA, 0.866 mg AIBN and 5 mL anisole into the reaction flask, the molar ratio of PDKA, AIBN and OEGMA is 1:0.33:100, 60 °C After the reaction was completed, 200 mL of ether was precipitated three times to remove the monomer, and vacuum-dried to obtain polyacrylic acid-4-(3-oxo-3-phenylpropionyl)phen...

Embodiment 3

[0075] 1.45g of 4-(3-oxo-3-phenylpropionyl)phenyl methacrylate (DKMA), 4.15mg of chain transfer agent-2-phenylpropan-2-dithiobenzoate (CDB ), 0.826mg AIBN, and 10mL anisole were added to the reaction flask, the molar ratio of DKMA, AIBN and CDB was 310:0.33:1, reacted at 70°C for 12 hours, dissolved and precipitated in 300mL ether three times to remove small molecular monomers, Vacuum-dried to obtain polymethacrylic acid-4-(3-oxo-3-phenylpropionyl)phenyl ester (PDKMA), the yield was 53%, the nuclear magnetic calculation degree of polymerization was 168, and the SEC number average molecular weight was 34.8kDa, The molecular weight distribution was 1.28.

[0076] Add 0.52g N-isopropylacrylamide (NIPAM), 0.373g PDKMA, 1.519mg AIBN and 5mL anisole into the reaction flask, the molar ratio of PDKMA, AIBN and NIPAM is 1:0.33:728, react at 60°C 8h, after the reaction, 200mL ether precipitated 3 times to remove the monomer, and vacuum dried to obtain polymethacrylic acid-4-(3-oxo-3-ph...

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Abstract

The invention discloses amphiphilic segmented copolymers, nanoparticles containing the amphiphilic segmented copolymers, a preparation method of the amphiphilic segmented copolymers and a use of the nanoparticles. The amphiphilic segmented copolymers are shown in the structural formulas (I) to (IV). In the structural formulas (I) to (IV), R1 represents H or methyl, R2, R3 and R5 represent H, alkyl or aryl, R4 represents hydroxyl or methyl, x is an integer of 3-20, Spacer is a spacer arm, the spacer arm is optional, and when the spacer arm exists, the spacer arm is one of an ester group, an alkyl group, a triazole group and a thioether group. The nanoparticle obtained by chelating of the amphiphilic segmented copolymer and rare earth ions has good biocompatibility, has excellent fluorescence imaging performances and MRI imaging performances and has a wide application value in the field of medicine and biology and especially in breast cancer diagnosis and treatment.

Description

technical field [0001] The invention belongs to the field of polymer material synthesis and biomedicine, and in particular relates to a fluorescence-MRI dual-function probe and carrier and its application in the field of biomedicine. Background technique [0002] In the past ten years, molecular imaging technology has developed rapidly. It can not only perform live imaging at the tissue level, cell level, and even molecular level to display its biological behavior, but also conduct qualitative and quantitative research on specific molecules (Nature , 2008, 452(7187):580-590). Among today's various molecular imaging technologies, MRI is one of the most mature imaging technologies. It is a non-invasive medical diagnostic technology that can provide high-resolution tissue information and three-dimensional structural imaging at the submillimeter level. Currently used in clinical magnetic resonance imaging diagnosis of T 1 The contrast agent is mainly a complex of gadolinium, b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F293/00C08F220/30C08F220/28C08F220/54C08F226/10C12Q1/02A61K49/12A61K49/00
Inventor 孙继红杨晓明凌君曹方义刘菲
Owner ZHEJIANG UNIV
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