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Phospholipid-like amphiphilic block copolymer-based ultrasonic contrast agent and preparation method thereof

A technology of amphiphilic block and ultrasound contrast agent, which can be applied in echo/ultrasonic imaging agent, analysis of solids with sound wave/ultrasonic wave/infrasonic wave, material analysis with sound wave/ultrasonic wave/infrasonic wave, etc. It can solve problems such as shell rupture, To achieve the effect of long duration, enhanced image effect and uniform particle size distribution

Active Publication Date: 2020-10-02
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the shell of the hard-shelled ultrasound contrast agent also ruptures above a certain pressure threshold

Method used

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  • Phospholipid-like amphiphilic block copolymer-based ultrasonic contrast agent and preparation method thereof
  • Phospholipid-like amphiphilic block copolymer-based ultrasonic contrast agent and preparation method thereof
  • Phospholipid-like amphiphilic block copolymer-based ultrasonic contrast agent and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] 1. The preparation of phospholipid-like amphiphilic block copolymer-based ultrasound contrast agent, the specific steps are as follows:

[0056] 1) Preparation of amphiphilic block copolymer polymer PCL 43 -b-PMPC 25 :

[0057] ①Preparation of PCL first: lauryl alcohol (0.82g, 0.004mol), ε-CL (10.13g, 0.089mol) and Sn(Otc) 2 (4.05 g, 0.01 mol) was added to the reaction vessel. remove the O 2 and residual water. The reaction was carried out under vacuum at 120°C for 24 hours. Dissolve the crude product in CH 2 Cl 2 , and purified by cold methanol precipitation to obtain PCL.

[0058] ②Prepare PCL-Br next: Dissolve the PCL-OH (7.00g, 0.002mol) and triethylamine (0.96mL, 0.007mmol) obtained in ① in tetrahydrofuran (THF); 2 In an atmosphere of 2-bromoisobutyryl bromide (0.85mL, 0.0069mmol) was added dropwise to the above solution at -20°C; the reaction was carried out at room temperature for 48-72 hours, and passed through a column of neutral alumina to remove Qua...

Embodiment 2

[0074] The PCL-b-PMPC contrast agent was prepared by a shearing method different from that in Example 1.

[0075] The specific preparation process of PCL-b-PMPC phospholipid block polymer nano-ultrasound contrast agent prepared by shearing method is as follows:

[0076] Weigh 3 mg of PCL-b-PMPC copolymer and 1 mg of DPPE-mPEG 5000 and dissolve them in 567 μL of tetrahydrofuran (THF) and 283 μL of methanol (MeOH) (2:1, v / v). PBS buffer (0.01M, pH=7.4), and then 150 μL of perfluoropentane (PFP) was added. Under the condition of ice-water bath, add liquid perfluoropentane, adopt the electric internal cutting homogenization method, the homogenization speed is 12000-30000rpm, and the homogenization time is 1-3min. After homogenization, a milky white product wrapped with perfluoropentane Block polymer mixture.

[0077] The above mixed solution is phase-transformed with a therapeutic ultrasound instrument to form a PCL-b-PMPC phospholipid amphiphilic block copolymer-based ultrasoun...

Embodiment 3

[0078] Embodiment 3 freeze-drying method prepares PCL-b-PMPC contrast agent

[0079] The specific preparation process of the PCL-b-PMPC phospholipid amphiphilic block copolymer base ultrasound contrast agent prepared by freeze-drying method is as follows:

[0080] Weigh 3 mg of PCL-b-PMPC copolymer and 1 mg of DPPE-mPEG 5000 and dissolve them in 567 μL of tetrahydrofuran (THF) and 283 μL of methanol (MeOH) (2:1, v / v). PBS buffer (0.01M, pH=7.4), and then 150 μL of perfluoropentane (PFP) was added. Under the condition of ice-salt water bath, conduct ultrasonic vibration, probe frequency 24KHz, power 35W, ultrasonic on 3s, off 6s, act for 3min, form a milky white suspension, then centrifuge under 3000g centrifugal force for 5min, discard the supernatant, each Add 6 mL of 10 wt% sucrose solution for resuspension. 10mL vials were used, divided into 2mL volumes per bottle, pre-frozen in a -20°C refrigerator overnight, and freeze-dried in a freeze dryer for 24 hours, in which the ...

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Abstract

The invention belongs to the field of ultrasonic image diagnosis, and particularly relates to a phospholipid-like amphiphilic block copolymer-based ultrasonic contrast agent and a preparation method thereof. The invention provides the phospholipid-like amphiphilic block copolymer-based ultrasonic contrast agent. The ultrasonic contrast agent comprises a shell and a core, wherein the shell is an amphiphilic block copolymer polycaprolactone-b-polymethacryloyloxyethyl phosphorylcholine, and the core is an ultrasonic responder. The phospholipid-like amphiphilic block copolymer-based ultrasonic contrast agent prepared by the method is relatively uniform in particle size distribution, obviously superior to a phospholipid-based ultrasonic contrast agent in stability and more suitable for ultrasonic diagnosis and treatment research; and the problem of deficiency in pressure resistance and mechanical index change resistance of an existing ultrasonic contrast agent can be solved, and the application range of the ultrasonic contrast agent is expanded.

Description

technical field [0001] The invention belongs to the field of ultrasonic image diagnosis, and in particular relates to a phospholipid-like amphiphilic block copolymer-based ultrasonic contrast agent and a preparation method thereof. Background technique [0002] Ultrasound contrast agents can enhance the contrast effect of ultrasonographic images and significantly improve the accuracy of ultrasonic diagnosis. They are widely used in the field of clinical diagnosis and have great application potential in ultrasound-mediated therapy. However, most of the ultrasonic contrast agents currently used in clinical practice are composed of small molecule phospholipids or albumin wrapped inert gas, which have shortcomings such as large polydispersity or short half-life (<10min), which limits its further application in imaging and treatment. application. [0003] In order to enhance the stability of ultrasound contrast agents, materials with higher stiffness than phospholipids have b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K49/22A61K47/34G01N29/06G01N29/032C08F293/00C08F230/02
CPCA61K47/34A61K49/221A61K49/223C08F230/02C08F293/005C08F2438/01G01N29/032G01N29/0654
Inventor 邱逦罗祥林黄建波阎锋程冲马朗马田王丽芸向茜
Owner WEST CHINA HOSPITAL SICHUAN UNIV
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