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Vital staining contrast agent by using polyuronide as vector, as well as preparation method and application thereof

A technology of polyuronic acid and polyuronic acid, which is applied in the field of in vivo dyeing contrast agent and its preparation, can solve the problems of poor transferability, long residence time, slow entry, etc.

Inactive Publication Date: 2015-12-16
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Aiming at the problems in the prior art that cannot be actively targeted, slow entry, poor transferability, and too long residence time, the present invention provides a living body dyeing contrast agent with polyuronic acid as a carrier and its preparation method and application

Method used

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  • Vital staining contrast agent by using polyuronide as vector, as well as preparation method and application thereof
  • Vital staining contrast agent by using polyuronide as vector, as well as preparation method and application thereof
  • Vital staining contrast agent by using polyuronide as vector, as well as preparation method and application thereof

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specific Embodiment approach

[0046] The technical solutions of the present invention will be further described below in conjunction with the drawings and embodiments.

[0047] When described polyuronic acid is polymannuronic acid, concrete molecular formula is as follows:

[0048]

[0049] no 1 is an integer, n 2 , n 3 and n 4 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. Ligand C is a vital dye.

[0050] When the polyuronic acid is polyguluronic acid, the specific molecular formula is as follows:

[0051]

[0052] no 1 is an integer, n 2 , n 3 and n 4 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. Ligand C is a vital dye.

[0053] When described polyuronic acid is polygalact...

Embodiment 1

[0057] The polyuronic acid carrier is polymannuronic acid (PM); n 1 =0n 2 =18n 3 =61n 4 =21; X is a nitrogen atom (N); linker 1 、linker 2 For dimethylene amino, no linker 3 ; Mannose receptor (MBP) recognition group (ligand A), molar content is 0; Part B is metal chelating agent DTPA, and molar content is 18%; Part C is vital dye toluidine blue, molar content It is 21%; the paramagnetic metal is gadolinium (Gd); the contrast agent PM-TB-GdDTPA is obtained. There are the following steps:

[0058]

[0059] Dissolve polymannuronic acid PM3.52g and acylating reagent EDC (1.92g, 10mmol) in 100ml of distilled water, stir at 60°C for 5h, then cool down to room temperature, slowly add alkyldiamine compounds ethylenediamine and Vital dye toluidine blue (0.306g, 1mmol), stirred overnight at room temperature. After the reaction was completed, the reaction solution was put into a dialysis bag (cut-off 3500), dialyzed with 3L of distilled water, and the water was changed every 4...

Embodiment 2

[0065] The polyuronic acid carrier is polygalacturonic acid (GA); n 1 =11n 2 =16n 3 =63n 4 =10; X is a nitrogen atom (N); linker 1 、linker 2 For dimethylene amino, no linker 3 ; Mannose receptor (MBP) recognition group (ligand A), molar content is 0; Part B is metal chelating agent DTPA, molar content is 16%; Part C is vital dye Evans blue, molar content 10%; the paramagnetic metal is gadolinium (Gd); the contrast agent GA-EB-GdDTPA is obtained. There are the following steps:

[0066]

[0067] Dissolve polygalacturonic acid GA3.12g and acylating reagent EDC (1.92g, 10mmol) in 100ml of distilled water, stir at 60°C for 5h, then cool down to room temperature, slowly add alkyldiamine compound ethylenediamine under stirring and vital dye toluidine blue (0.306g, 1mmol), stirred overnight at room temperature. After the reaction was completed, the reaction solution was put into a dialysis bag (cut-off 3500), dialyzed with 3L of distilled water, and the water was changed ev...

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Abstract

The invention relates to medical contrast agents, and particularly relates to a vital staining contrast agent by using polyuronide as a vector, as well as a preparation method and an application thereof. A macromolecular contrast agent with excellent water solubility is prepared by using polyuronide as the vector, mannose or mannose derivatives as a mannose receptor (MBP) recognition group and a paramagnetic metal ion chelate as a magnetic resonance imaging group, the lymphoid tissue binding force is improved, and the aim of binding mannose or mannose derivative group which is introduced into the synthesized contrast agent molecules with the mannose receptor enriched in the lymphoid tissues can be achieved. Furthermore, preoperative lymph imaging mapping is beneficial to intraoperative sentinel lymph node mapping and lymph node cleaning operation in a delicate tumor surgical operating process, and can be widely applied to breast cancer, head and neck cancer, melanotic cancer and other preoperative sentinel lymph node mappings. The contrast agent can be used for simultaneously meeting the requirement for biopsy and magnetic resonance imaging, and is an excellent difunctional lymph target contrast agent.

Description

technical field [0001] The invention relates to a medical contrast agent, in particular to a living body dyeing contrast agent with polyuronic acid as a carrier and its preparation method and application. Background technique [0002] The lymphatic system is a network structure composed of lymph nodes and lymphatic vessels, which are distributed roughly parallel to capillaries and venous vessels, and spread 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 detect metastatic cancer cells first. Metastatic cancer cells use the SLN as an accumulation site, 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, lymphatic system...

Claims

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Application Information

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IPC IPC(8): A61K49/12
CPCA61K49/12
Inventor 江涛万升标张南赵洺良
Owner OCEAN UNIV OF CHINA
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