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Tumor-targeted nuclear magnetic resonance/fluorescence dual-modal imaging contrast agent and its preparation and application

A nuclear magnetic resonance and tumor-targeting technology, applied in nuclear magnetic resonance imaging and near-infrared fluorescence imaging, tumor-targeted nuclear magnetic resonance/fluorescence dual-mode imaging contrast agent and its preparation field, can solve the problem of easy aggregation, probe Lack of tumor targeting and other issues, to achieve high quantum yield, enhanced MRI signal intensity and near-infrared fluorescence signal intensity, and low toxicity and side effects

Active Publication Date: 2020-01-07
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the probe has a hydrated particle size of 32nm, is prone to aggregation, and the probe lacks tumor targeting

Method used

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  • Tumor-targeted nuclear magnetic resonance/fluorescence dual-modal imaging contrast agent and its preparation and application
  • Tumor-targeted nuclear magnetic resonance/fluorescence dual-modal imaging contrast agent and its preparation and application
  • Tumor-targeted nuclear magnetic resonance/fluorescence dual-modal imaging contrast agent and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Preparation of tumor-targeted nuclear magnetic resonance and near-infrared fluorescence dual-mode imaging contrast agent:

[0058] (1) Preparation of NMR amphiphile: Take 1.0026g of tri-tert-butyl 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) and dissolve it in dichloromethane (DCM), and 0.2448g N-hydroxysuccinimide (NHS) under the action of 1.8087g dicyclohexylcarbodiimide (DCC), activated at room temperature for 2h, then added 0.5065g hexadecylamine, stirred at room temperature for 12h , after suction filtration, the reaction product was precipitated with a large amount of ether, and vacuum-dried to obtain a milky white powder; then added to a mixture of trifluoroacetic acid (TFA) and DCM, stirred and reacted for 2 hours, the reaction solvent was removed by rotary evaporation, and the reaction product was washed with petroleum ether. Vacuum-dried to obtain a white oil; redissolve the white oil in water, add 0.3481 g of gadolinium acetate hydrate at t...

Embodiment 2

[0063] Preparation of tumor-targeted nuclear magnetic resonance and near-infrared fluorescence dual-mode imaging contrast agent:

[0064] (1) Preparation of NMR amphiphile: Take 1.0026g of tri-tert-butyl 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) and dissolve it in dichloromethane (DCM), and 0.2448g N-hydroxysuccinimide (NHS) under the action of 1.8087g dicyclohexylcarbodiimide (DCC), activate at room temperature for 2h, then add 0.5660g carbooctadecylamine, stir at room temperature Reaction for 12 hours, after suction filtration, precipitate the reaction product with a large amount of ether, and dry it in vacuum; then add it to the mixture of trifluoroacetic acid (TFA) and DCM, stir and react for 2 hours, remove the reaction solvent by rotary evaporation, wash the reaction product with petroleum ether, vacuum Dry to obtain a white oil; redissolve the white oil in water, add gadolinium acetate hydrate at the same time, adjust the pH of the solution to 5-6,...

Embodiment 3

[0069] Preparation of tumor-targeted nuclear magnetic resonance and near-infrared fluorescence dual-mode imaging contrast agent:

[0070](1) Preparation of NMR amphiphile: Take 1.0026g of tri-tert-butyl 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) and dissolve it in dichloromethane (DCM), and 0.2448g N-hydroxysuccinimide (NHS) under the effect of 1.8087g dicyclohexylcarbodiimide (DCC) activated at room temperature for 2h, then added 1.571g phospholipids, stirred at room temperature for 12h, pumped After filtration, the reaction product was precipitated with a large amount of diethyl ether, dried in vacuo; then added to a mixture of trifluoroacetic acid (TFA) and DCM, stirred for 2 hours, and the reaction solvent was removed by rotary evaporation, the reaction product was washed with petroleum ether, and dried in vacuo to obtain a white oil matter; redissolve the white oil in water, add gadolinium acetate hydrate at the same time, adjust the pH of the solutio...

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Abstract

The invention provides a tumor-targeted nuclear magnetic resonance / fluorescence dual-mode imaging contrast agent and its preparation and application. The contrast agent is composed of a nuclear magnetic resonance amphiphile, a near-infrared fluorescent dye amphiphile and a tumor-targeting amphiphile in a solution. Nanoparticles formed by self-assembly can exist stably under physiological pH conditions, and can specifically accumulate and target tumor sites, significantly enhance the MRI signal intensity and near-infrared fluorescence signal intensity of tumor lesions, and improve the performance of nuclear magnetic resonance imaging and near-infrared fluorescence. Due to the specificity and sensitivity of fluorescence imaging scanning, it is expected to be used as a contrast agent for intraoperative fluorescence guidance and postoperative nuclear magnetic resonance monitoring in tumor resection surgery.

Description

technical field [0001] The invention relates to a contrast agent for imaging diagnosis, in particular to a tumor-targeting nuclear magnetic resonance / fluorescence dual-mode imaging contrast agent, a preparation method thereof, and an application in nuclear magnetic resonance imaging and near-infrared fluorescence imaging. Background technique [0002] In the early stage of cancer, if the physiological and morphological changes of diseased organs or tissues can be detected quickly and accurately, and corresponding imaging information can be given, it is of great significance for the early diagnosis of cancer. Contrast agents are such substances that are injected into specific tissues or organs of the human body to produce density or other differences from normal tissue parts and visualize these differences, thereby providing important clinical information about diseases. [0003] MRI (Magnetic Resonance imaging, MRI) is a technology that utilizes the hydrogen nuclei of water ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K49/10A61K49/18A61K49/00
Inventor 王辉辉谭明乾马小军吕国军
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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