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Polymer with targeted nuclear magnetic resonance imaging and fluorescence imaging functions, preparation method and application

A nuclear magnetic resonance and fluorescence imaging technology, which is used in nuclear magnetic resonance/magnetic resonance imaging contrast agents, general/multifunctional contrast agents, preparations for in vivo tests, etc. Clinical and market application potential, good application prospects, and the effect of excellent biocompatibility

Inactive Publication Date: 2020-07-10
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is: how to solve the problem of low recognition degree in nuclear magnetic resonance imaging, and provide a method for preparing a polymer with targeted nuclear magnetic resonance imaging and fluorescence imaging functions

Method used

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  • Polymer with targeted nuclear magnetic resonance imaging and fluorescence imaging functions, preparation method and application
  • Polymer with targeted nuclear magnetic resonance imaging and fluorescence imaging functions, preparation method and application
  • Polymer with targeted nuclear magnetic resonance imaging and fluorescence imaging functions, preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0043] In this embodiment, the targeted nuclear magnetic resonance imaging and fluorescence imaging polymers were prepared according to the following steps:

[0044] Step 1: Dissolve 1.3g of hydroxyethyl methacrylate and 2g of triethylamine in 20mL of dichloromethane, add 2.2g of bromoacetyl bromide, stir at 0°C for 12h, and separate the resulting product through a silica gel column (eluent is acetic acid ethyl ester and n-hexane), spin-dried, then mixed with 3.3g 1,4,7,10-tetraazacyclododecane-1,4,7-tri-tert-butyl triacetate and 2.5g potassium carbonate in acetonitrile reaction in China for 12 hours, the resulting product was filtered and extracted to obtain the product tri-tert-butyl methacrylate-1,4,7,10-tetraazacyclododecane-1,4,7-triacetate ;

[0045] Step 2: Dissolve 28 mg of 4-cyano-4-(thiobenzoyl)valeric acid in 10 mL of 1,4-dioxane, add it to a polymer bottle, and then add 1.2 g of polyethylene glycol methacrylate Esters, 0.55g hydroxyethyl methacrylate-1,4,7,10-tet...

Embodiment 2

[0056] In this embodiment, the targeted nuclear magnetic resonance imaging and fluorescence imaging polymers were prepared according to the following steps:

[0057] Step 1: Dissolve 3 g of hydroxyethyl methacrylate and 5 g of triethylamine in 50 mL of dichloromethane, add 5 g of bromoacetyl bromide, stir at 0° C. for 6 h, and separate the resulting product through a silica gel column (eluent is ethyl acetate and n-hexane), spin-dried, then reacted with 6g of 1,4,7,10-tetraazacyclododecane-1,4,7-tri-tert-butyl triacetate and 5g of potassium carbonate in acetonitrile for 6h, the obtained After the product is filtered and extracted, the product tri-tert-butyl methacrylate-1,4,7,10-tetraazacyclododecane-1,4,7-triacetate is obtained;

[0058] Step 2: Dissolve 56 mg of 4-cyano-4-(thiobenzoyl)valeric acid in 15 mL of 1,4-dioxane, add it to a polymer bottle, and then add 2 g of polyethylene glycol methacrylate , 1g of hydroxyethyl methacrylate-1,4,7,10-tetraazacyclododecane-1,4,7-tr...

Embodiment 3

[0066] In this embodiment, the targeted nuclear magnetic resonance imaging and fluorescence imaging polymers were prepared according to the following steps:

[0067] Step 1: Dissolve 10 g of hydroxyethyl methacrylate and 15 g of triethylamine in 150 mL of dichloromethane, add 17 g of bromoacetyl bromide, stir at 0° C. for 24 h, and separate the resulting product through a silica gel column (eluent is ethyl acetate and n-hexane), spin-dried, then reacted with 8g of 1,4,7,10-tetraazacyclododecane-1,4,7-tri-tert-butyl triacetate and 8g of potassium carbonate in acetonitrile for 24h. After the obtained product is filtered and extracted, the product tri-tert-butyl methacrylate-1,4,7,10-tetraazacyclododecane-1,4,7-triacetate is obtained;

[0068] Step 2: Dissolve 100mg of 4-cyano-4-(thiobenzoyl)valeric acid in 20mL of 1,4-dioxane, add it to a polymer bottle, and then add 9g of polyethylene glycol methacrylate , 4g of hydroxyethyl methacrylate-1,4,7,10-tetraazacyclododecane-1,4,7-tr...

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Abstract

The invention discloses a polymer with targeted nuclear magnetic resonance imaging and fluorescence imaging functions, a preparation method and an application, and belongs to the technical field of nuclear magnetic resonance imaging. The preparation method comprises the following steps: S1, preparing a preliminary product; S2, preparing a copolymer; S3, preparing a block copolymer; S4, preparing an end-modified block copolymer; and S5, preparing the fluorescent targeted nuclear magnetic resonance imaging polymer with high relaxation rate. In the step S1, an eluent used when an obtained productis separated by a silica gel column is a mixed solution of ethyl acetate and normal hexane, and the volume ratio of the ethyl acetate to the normal hexane is 1: 3. The polymer prepared by the invention has the functions of nuclear magnetic resonance imaging and fluorescence imaging at the same time, and has a good application prospect in clinical diagnosis and guided surgical resection; the polymer has low toxicity, excellent biocompatibility and low cytotoxicity, and is a safe material; and the structure is stable, the relaxation rate is high, and high clinical and market application potential is achieved.

Description

technical field [0001] The invention relates to the technical field of nuclear magnetic resonance imaging, in particular to a polymer with targeted nuclear magnetic resonance imaging and fluorescence imaging functions, a preparation method and an application. Background technique [0002] Magnetic resonance imaging is an effective clinical diagnostic and therapeutic method with extremely high spatial resolution and contrast. Gadolinium (Ⅲ) complexes have been proven to be particularly effective MRI contrast agents. Dotalin has been widely used clinically, and more than 30% of patients need them to accelerate the relaxation rate of water protons in the body, thereby Enhances the contrast of different biological tissues and the localization between normal and diseased tissues. [0003] Fluorescence imaging is one of the broadest and most powerful visualization techniques in biological research and clinical diagnosis, with selectivity, visibility and tunability. Fluorescence ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F8/34C08F8/30C08F8/32C08F293/00C08F212/34C08F283/06C08F220/36A61K49/00A61K49/06
CPCC08F8/34C08F8/30C08F8/32C08F293/005C08F212/34C08F283/065A61K49/0002A61K49/0019A61K49/06
Inventor 何涛夏彬闫旭陆杨单文静范雨萌骆辰恺栾钊柯兆琛
Owner HEFEI UNIV OF TECH
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