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PEGylated amphiphilic alternating copolymer metal chelating agent, metal chelate as well as preparation method and application of PEGylated amphiphilic alternating copolymer metal chelating agent and metal chelate

A technology of metal chelating agent and alternating copolymer, which is applied in the field of polymers and can solve the problems of short duration of enhanced contrast and short residence time

Active Publication Date: 2022-05-27
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of small molecule contrast agent will be quickly metabolized with the blood circulation, and the residence time in the body is very short, resulting in a shorter duration of enhanced contrast

Method used

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  • PEGylated amphiphilic alternating copolymer metal chelating agent, metal chelate as well as preparation method and application of PEGylated amphiphilic alternating copolymer metal chelating agent and metal chelate
  • PEGylated amphiphilic alternating copolymer metal chelating agent, metal chelate as well as preparation method and application of PEGylated amphiphilic alternating copolymer metal chelating agent and metal chelate
  • PEGylated amphiphilic alternating copolymer metal chelating agent, metal chelate as well as preparation method and application of PEGylated amphiphilic alternating copolymer metal chelating agent and metal chelate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The preparation of PEGylated amphiphilic alternating copolymer metal chelator PEG-P(L-alt-R)-PEG, its chemical formula is shown in formula IV:

[0043]

[0044] First prepare the small molecule metal chelator L and its precursor, the specific method is as follows: take 2g (11mmol) of L-proline methyl ester hydrochloride, add 30mL of acetonitrile and 0.8802g (5mmol) of 2,6-pyridine dichloride, 7.601g (55mmol) potassium chloride and 0.0102g (0.14mmol) potassium iodide were added under stirring, and the mixed solution was reacted at 45°C for 19 hours. After confirming that the reaction was complete by TLC dot plate, all the reagents in the bottle were transferred to a centrifuge tube. , and centrifuged at 5000rpm / s for 10min to remove the inorganic salt precipitate. Then, the upper layer solution in the centrifuge tube was filtered under reduced pressure through a sand core funnel, and the solvent was removed by rotary evaporation. It was separated and purified by sili...

Embodiment 2

[0048] PEGylated amphiphilic alternating copolymer manganese chelate PEG-P(MnL-alt-R)-PEG is prepared, and its chemical formula is shown in formula V:

[0049]

[0050] 0.25g PEG-P(L-alt-R) was dissolved in 0.4mL DMSO, and 0.5M Tris buffer (pH 6.5) was added dropwise under ultrasonic conditions to obtain PEG-P(L-alt-R) aqueous dispersion. Subsequently, 5 equivalents of manganese chloride tetrahydrate was dissolved with a small amount of Tris buffer, added to the above dispersion under nitrogen protection, and stirred for 24 h under nitrogen. The free manganese ions were removed by dialysis for three days, and finally concentrated to obtain PEG-P(MnL-alt-R)-PEG, a PEGylated amphiphilic alternating copolymer manganese chelate.

Embodiment 3

[0052] PEGylated Amphiphilic Alternating Copolymer 68 Ga chelate PEG-P ( 68 Preparation of GaL-alt-R)-PEG

[0053] 0.25g PEG-P(L-alt-R) was dissolved in 0.4mL DMSO, and 0.5M Tris buffer (pH 6.5) was added dropwise under ultrasonic conditions to obtain PEG-P(L-alt-R) aqueous dispersion. The DMSO was removed by dialysis against deionized water for two days, and the stock solution of 25 mg / mL was obtained after concentration. Then a small amount of 68 GaCl 3 (50 μL) was added dropwise to the constantly stirring PEG-P (L-alt-R) solution, chelated at 80° C. for 15-30 min, and the chelation efficiency was above 90%. The pH was then adjusted to 7.4 with 0.1 M sodium hydroxide for PET imaging.

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Abstract

The invention relates to a pegylated amphiphilic alternating copolymer metal chelating agent PEG-P (L-alt-R)-PEG, a metal chelate PEG-P (ML-alt-R)-PEG as well as a preparation method and application of the metal chelate PEG-P (L-alt-R)-PEG. The preparation method of the pegylated amphiphilic alternating copolymer metal chelating agent is simple, various metal ions can be effectively chelated, the pegylated amphiphilic alternating copolymer metal chelating agent has good biocompatibility, and the in-vivo circulation time is prolonged. The PEGylated amphiphilic alternating copolymer metal chelating agent has a wide application prospect in the fields of magnetic resonance imaging (MRI), positron emission tomography (PET), single photon emission computed tomography (SPECT) and fluorescence imaging, and can be applied to the fields of magnetic resonance imaging (MRI), positron emission tomography (PET), single photon emission computed tomography (SPECT) and fluorescence imaging.

Description

technical field [0001] The invention belongs to the technical field of polymers, and in particular relates to a PEGylated amphiphilic alternating copolymer metal chelating agent PEG-P(L-alt-R)-PEG, metal chelating compound PEG-P(ML-alt- R)-PEG and its preparation method and application. Background technique [0002] Since the last century, with the emergence of magnetic resonance imaging (Magnetic Resonance Imaging, MRI), nuclear medicine imaging (Nuclear Medicine Imaging), optical imaging (Optical Imaging) and other technologies, medical imaging technology has gradually become an indispensable part of clinical disease diagnosis. Fewer tools. These imaging techniques often require corresponding contrast agents to ensure the accuracy and precision of their imaging and diagnosis. Contrast agent is a substance that has distribution differences between different tissues after being injected into the human body or animal body, thereby improving the imaging contrast between tiss...

Claims

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Application Information

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IPC IPC(8): C08G18/75C08G18/83C08G18/66C08G18/48C08G18/38A61K51/06A61K51/04
CPCC08G18/758C08G18/6666C08G18/4833C08G18/3844C08G18/83A61K51/065A61K51/0455
Inventor 艾华刘潇钦傅声祥蔡忠源
Owner SICHUAN UNIV
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