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Amphiphilic block copolymer and nanoparticles comprising the same, preparation method and application thereof

A technology of amphiphilic blocks and nanoparticles, which is applied in biochemical equipment and methods, measurement/inspection of microorganisms, preparations for in vivo tests, etc., can solve problems such as short residence time, achieve narrow emission peaks, and process Simple and efficient, long fluorescence lifetime effect

Active Publication Date: 2017-10-13
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 block copolymer and nanoparticles comprising the same, preparation method and application thereof
  • Amphiphilic block copolymer and nanoparticles comprising the same, preparation method and application thereof
  • Amphiphilic block copolymer and nanoparticles comprising the same, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0063] Add 1.810g oligoethylene glycol methacrylate (OEGMA), 0.564mg PDKMA, 1.519mg AIBN and 5mL anisole into the reaction flask. The molar ratio of PDKMA, AIBN and OEGMA is 1:0.33:130, 60℃ React for 12 hours. After the reaction is over, 200mL of ether is precipitated three times to rem...

Embodiment 2

[0072] Add 1.2g of acrylic acid-4-(3-oxo-3-phenylpropionyl)phenyl ester (DKA), 5.55mg of chain transfer agent dithiobenzoic acid-2-phenylpropan-2-ester (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℃ for 24h, dissolve the precipitate in 200mL ether three times to remove small monomers, and dry in vacuum. Polyacrylic acid-4-(3-oxo-3-phenylpropionyl)phenyl ester (PDKA) was obtained, the yield was 20%, the degree of polymerization calculated by NMR was 51, the SEC number average molecular weight was 15.8kDa, and the molecular weight distribution was 1.30 .

[0073] Add 0.8g oligoethylene glycol methacrylate (OEGMA), 0.24g PDKA, 0.866mg AIBN and 5mL anisole into the reaction flask, the molar ratio of PDKA, AIBN and OEGMA is 1:0.33:100, 60℃ React for 18 hours. After the reaction is over, 200 mL of ether is precipitated three times to remove the monomer, and dried under vacuum to obtain polyacrylic acid-...

Embodiment 3

[0075] 1.45g methacrylic acid-4-(3-oxo-3-phenylpropionyl)phenyl ester (DKMA), 4.15mg chain transfer agent dithiobenzoic acid-2-phenylpropan-2-ester (CDB ), 0.826mg AIBN, 10mL anisole were added to the reaction flask, the molar ratio of DKMA, AIBN and CDB was 310:0.33:1, reacted at 70℃ for 12h, dissolved and precipitated in 300mL ether three times to remove small monomers, After vacuum drying, polymethacrylic acid-4-(3-oxo-3-phenylpropionyl)phenyl ester (PDKMA) was obtained, the yield was 53%, the degree of polymerization calculated by nuclear magnetic field was 168, and the SEC number average molecular weight was 34.8kDa. The molecular weight distribution is 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℃ 8h, after the completion of the reaction, 200mL of ether was precipitated three times to remove the monomers, and dried under vacuum ...

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Abstract

The invention discloses an amphiphilic block copolymer, nanoparticles containing the copolymer, its preparation method and application. The structure of the amphiphilic block copolymer is as in formula (I) to formula (IV). As shown in one, in formula (I)~(IV), R1 is H or methyl; R2, R3, R5 are H or alkyl, aryl; R4 is hydroxyl or methyl; x=3~20 integer ; Spacer is a spacer arm, which may not have a spacer arm. If there is a spacer arm, it includes one of an ester group, an alkyl group, a triazole group, and a thioether group. The nanoparticles formed after the amphiphilic block copolymer is chelated with rare earth ions have good biocompatibility, and have excellent fluorescence imaging performance and MRI imaging performance, and are used in the fields of medicine and biology, especially for the diagnosis and treatment of breast cancer and other tumors It has wide application value.

Description

Technical field [0001] The invention belongs to the field of polymer material synthesis and biomedicine, and specifically relates to a fluorescent-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 in vivo imaging at the tissue level, cell level, and even molecular level to show its biological behavior, but also perform qualitative and quantitative studies on specific molecules (Nature , 2008, 452(7187): 580-590). Among the various molecular imaging technologies available today, 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 structure imaging at the sub-millimeter level. T currently used for clinical MRI diagnosis 1 The contrast agent is mainly a gadolinium complex, but it stays in the blood...

Claims

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Application Information

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Patent Type & Authority Patents(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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