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Lymph targeted nuclear magnetic resonance imaging contrast agent with brown algal polysaccharide serving as carrier and preparation method and application of lymph targeted nuclear magnetic resonance imaging contrast agent with brown algal polysaccharide serving as carrier

一种褐藻多糖、淋巴靶向的技术，应用在体内试验用的配制品、医药配方、乳状液输送等方向，能够解决停留时间长、转移性不强、不能主动靶向等问题，达到信号强化率和强化时间增强、清晰绘图和精确定位、提高淋巴组织结合力的效果

Active Publication Date: 2016-02-24
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Aiming at the problems in the prior art that cannot be actively targeted, slow entry, poor transferability and long residence time, the present invention provides a lymphatic targeting contrast agent using fucoidan as a carrier and its preparation method and application

Method used

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  • Lymph targeted nuclear magnetic resonance imaging contrast agent with brown algal polysaccharide serving as carrier and preparation method and application of lymph targeted nuclear magnetic resonance imaging contrast agent with brown algal polysaccharide serving as carrier
  • Lymph targeted nuclear magnetic resonance imaging contrast agent with brown algal polysaccharide serving as carrier and preparation method and application of lymph targeted nuclear magnetic resonance imaging contrast agent with brown algal polysaccharide serving as carrier
  • Lymph targeted nuclear magnetic resonance imaging contrast agent with brown algal polysaccharide serving as carrier and preparation method and application of lymph targeted nuclear magnetic resonance imaging contrast agent with brown algal polysaccharide serving as carrier

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specific Embodiment approach

[0060] The technical solution of the present invention will be further described below in conjunction with the drawings and embodiments.

[0061] When the fucoidan is polymannuronic acid, the specific molecular formula is as follows:

[0062]

[0063] n 1 Is an integer, n 2 And n 3 Is a positive integer, X is O, N or S; linker is an alkyl group, an aromatic group or a heterocyclic group. Ligand A is mannose or a mannose derivative. Ligand B is a paramagnetic metal chelate fragment.

[0064] When the fucoidan is polyguluronic acid, the specific molecular formula is as follows:

[0065]

[0066] n 1 Is an integer, n 2 And n 3 Is a positive integer, X is O, N or S; linker is an alkyl group, an aromatic group or a heterocyclic group. Ligand A is mannose or a mannose derivative. Ligand B is a paramagnetic metal chelate fragment.

Embodiment 1

[0068] The carrier of fucoidan is polymannuronic acid (PM); n 1 = 6n 2 = 16n 3 =78; X is nitrogen atom (N); linker 1 And linker 2 It is a dimethylamino group; the mannose receptor (MBP) recognition group (ligand A) with a molar content of 0; ligand B is a metal chelator DTPA with a molar content of 16%; the paramagnetic metal is gadolinium (Gd ); Get the contrast agent PM-GdDTPA. There are the following reaction processes and steps:

[0069]

[0070] Dissolve 1.78 g of marine brown algae polysaccharide polymannuronic acid (PM) and acylation reagent EDC (1.92 g, 10 mmol) in 50 mL deionized water, and slowly add alkyl diamine compound ethylene diamine (3.0 g, 50mmol), react at room temperature for 12h. After the reaction, the solution was placed in a dialysis bag with a cut-off volume of 3500 and dialyzed in deionized water for 48 hours. After the dialysis, the solution was concentrated and freeze-dried to obtain 1.81 g of a white solid compound PM-N. The molar ratio of alkyl di...

Embodiment 2

[0082] The carrier of fucoidan is polyguluronic acid (PG); n 1 = 13n 2 = 19n 3 =46; X is nitrogen atom (N); linker 1 And linker 2 It is a dimethylamino group; the mannose receptor (MBP) recognition group (ligand A) with a molar content of 0; ligand B is a metal chelating agent DTPA with a molar content of 19%; the paramagnetic metal is gadolinium (Gd ); Get the contrast agent PG-GdDTPA. There are the following reaction processes and steps:

[0083]

[0084] Dissolve 2.3 g of marine fucoidan polyguluronic acid (PG) and acylation reagent EDC (2.48 g, 12.9 mmol) in 70 mL of deionized water, and slowly add alkyl diamine compound ethylene diamine in batches while stirring at room temperature (3.8g, 63.3mmol), react at room temperature for 12h. After the reaction, the solution was placed in a dialysis bag with a cut-off volume of 3500 and dialyzed in deionized water for 48 hours. After the dialysis, the solution was concentrated and lyophilized to obtain 2.01 g of white solid compoun...

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Abstract

The invention relates to contrast agents for medical science, in particular to a lymph targeted nuclear magnetic resonance imaging contrast agent with brown algal polysaccharide serving as a carrier and a preparation method and application of the lymph targeted nuclear magnetic resonance imaging contrast agent with the brown algal polysaccharide serving as the carrier. The macromolecular contrast agent high in water solubility is prepared by taking the brown algal polysaccharide as the carrier, taking mannose or mannose derivatives as a mannose receptor MBP (mannose binding protein) recognition group and taking paramagnetic metal ion chelates as a nuclear magnetic resonance imaging group. Lymph tissue binding force is increased, and combination of the mannose or mannose derivative group introduced into the synthetic contrast agent with mannose receptors enriched in lymph tissues is realized. In addition, after hypodermic injection of the contrast agent, lymph vessels and lymph glands are clearly developed under scanning of a nuclear magnetic resonance equipment, lymph gland signal enhancement rate of one side, with the contrast agent injected, of an animal body is remarkably increased while enhancement time is remarkably prolonged, distinct drawing and precise positioning of the lymph glands and the lymph vessels are realized, and a great significance to examination and diagnosis of lymphatic diseases is achieved.

Description

Technical field [0001] The invention relates to a medical contrast agent, in particular to a lymphatic targeting contrast agent using fucoidan as a carrier, and a preparation method and application thereof. Background technique [0002] The lymphatic system is a network structure composed of lymph nodes and lymph vessels. Its distribution is roughly parallel to capillaries and venous blood vessels and spreads all over the body. As an important part of the human immune system, the lymphatic system plays a key role in the spread of germs and the metastasis of cancer. Studies have shown that when breast cancer cells and melanoma cells metastasize, the sentinel lymph node (SLN) is the most likely to find metastatic cancer cells first. Metastatic cancer cells use SLN as an accumulation place, spread along the lymphatic vessels and invade the surrounding lymph nodes at all levels, and finally complete the spread of cancer cells throughout the body. Therefore, lymphangiography, as a m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K49/12A61K49/18
CPCA61K49/128A61K49/101A61K49/12
Inventor 江涛万升标尚伟张南赵洺良
Owner OCEAN UNIV OF CHINA
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