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Tyramine/diphosphonate hyaluronic acid macromolecular compound and hydrogel, and preparation method and application thereof

A polymer compound and bisphosphonate technology, applied in the field of bone repair materials, can solve the problems of weak tissue penetration and difficult bone repair materials to trace in vivo, and achieve the promotion of bone repair ability, good in vivo degradation characteristics, and good bone repair. The effect of repair ability

Inactive Publication Date: 2017-12-19
INST OF NUCLEAR PHYSICS & CHEM CHINA ACADEMY OF
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] For bone repair, in the stage of experimental research and actual clinical application, it is necessary to closely understand the distribution of bone repair materials in the body and the fixation of the target site, which requires bone repair materials to be traceable in vivo. Fluorescent labeling imaging techniques commonly used in research are difficult to track bone repair materials in vivo due to their poor tissue penetration

Method used

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  • Tyramine/diphosphonate hyaluronic acid macromolecular compound and hydrogel, and preparation method and application thereof
  • Tyramine/diphosphonate hyaluronic acid macromolecular compound and hydrogel, and preparation method and application thereof
  • Tyramine/diphosphonate hyaluronic acid macromolecular compound and hydrogel, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] In this example, the preparation method of tyramine / bisphosphonate-hyaluronic acid polymer compound is provided, the steps are as follows:

[0053] (1) Dissolve 200 mg of hyaluronic acid in 25 mL of pure water, add 16.66 mg of functionalized linker small molecule 3,3'-dithiobis(propionic hydrazide) (3,3'-Dithiobis(propionic hydrazide)) and Stir and mix well, then add the tyramine solution formed by dissolving 41.15mg tyramine in 1mL dimethyl sulfoxide (DMSO) and stir well, then add 76.5mg 1-hydroxybenzotriazole (HoBt) dissolved in 1mL HoBt solution formed in DMSO and stirred;

[0054] (2) Adjust the pH value of the mixed solution obtained in step (1) to 4.7 with 1mol / L hydrochloric acid, and then add 71.85 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC), stirred and reacted at room temperature for 16h;

[0055] (3) Regulate the pH value of the reaction solution obtained in step (2) to 8.7 with 1mol / L hydrochloric acid, then add 53.9mg dithiothr...

Embodiment 2

[0060] In this example, provide 131 The preparation method of the I-labeled tyramide / bisphosphonate-hyaluronic acid macromolecular compound is as follows:

[0061] Put 1mL of 1,3,4,6-tetrachloro-3α,6α-diphenyl glycoluril (Iodogen) solution into a 5mL plastic centrifuge tube, and then use a vacuum pump for 20min to form a lodogen coating on the bottom of the centrifuge tube .

[0062] The tyramine / bisphosphonate-hyaluronic acid macromolecular compound prepared in Example 1 was prepared into a 2 mg / mL solution with pH=7.4 and a concentration of 10 mmol / L PBS buffer solution, which was referred to as solution A, and Na 131 I use pH = 7.4, PBS buffer solution with a concentration of 10mmol / L to prepare a 10mCi / mL solution, which is referred to as solution B. Add 1mL of solution A to the centrifuge tube containing the lodogen coating, then add 1mCi of solution B, and then add Ultrapure water to 2mL, shake the reaction for 15min and then purify the reaction product by ethanol prec...

Embodiment 3

[0067] In this example, provide 99m The preparation method of the Tc-labeled tyramide / bisphosphonate-hyaluronic acid polymer compound is as follows:

[0068] The tyramine / bisphosphonate-hyaluronic acid macromolecular compound prepared in Example 1 was prepared into a 2 mg / mL solution with PBS buffer solution with a pH of 7.4 and a concentration of 10 mmol / L.

[0069] The compound shown in formula (I) is prepared into a solution of 10 mg / mL with physiological saline or PBS buffer, which is referred to as solution C. 99m The water-soluble salt of Tc is prepared into a solution with a concentration of 100mCi / mL with PBS buffer solution with a pH of 7.4 and a concentration of 10mmol / L, which is recorded as solution D. Take 1mL of solution C, and add 20μL of chlorinated chloride with a concentration of 1mg / mL to it. Stannous solution and 2mCi solution D, shaking reaction for 15min, the resulting crude product solution was purified with G25 Sephadex column, the preparation method o...

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Abstract

The invention belongs to the field of a bone repairing material, and provides a tyramine / diphosphonate hyaluronic acid macromolecular compound and a radionuclide marked tyramine / diphosphonate hyaluronic acid macromolecular compound, a preparation method of the tyramine / diphosphonate hyaluronic acid macromolecular compound and the radionuclide marked tyramine / diphosphonate hyaluronic acid macromolecular compound, hydrogel formed on the basis of the tyramine / diphosphonate hyaluronic acid macromolecular compound and the radionuclide marked tyramine / diphosphonate hyaluronic acid macromolecular compound, and the application of the hydrogel in the fields of biological material in vivo tracing and bone repairing. The two kinds of hydrogel provided by the invention serving as bone tissue repairing materials have good bone repair promoting capability in a living body; the radionuclide marked hydrogel is an in-vivo tracing bone tissue repairing material, not only can trace and know the material filling effect in vivo, but also can deeply know the degradation process through nuclear medicine imaging. In particular, the hydrogel marked by therapeutic radionuclides 188Re and 177Lu has a certain treatment effect on bone tissue necrosis inflammation or cancerization, and has double functions of imaging in vivo and repairing the bone tissues.

Description

technical field [0001] The invention belongs to the field of bone repair materials, and relates to a tyramine / bisphosphonate-hyaluronic acid macromolecular compound and a radionuclide-labeled tyramide / bisphosphonate-hyaluronic acid macromolecular compound, and a preparation method for the two. The hydrogels formed on the basis of them and the applications of the hydrogels. Background technique [0002] Most of the clinical treatment methods for large bone tissue necrosis, loss and fracture are traditional autologous bone transplantation, but this method is limited by the fact that the donor cannot meet the needs of large damaged bone repair. In medicine, bone substitute materials are mainly used to fix it. At present, the metal-inorganic bone substitute materials commonly used in medicine are not organic components of the human body, and the materials need to be manually fixed on the parts that need to be repaired. Some materials have a limited service life and require mult...

Claims

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Application Information

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IPC IPC(8): C08B37/08A61L27/20A61L27/52A61L27/54A61L27/58A61K51/06A61K51/12A61P19/08A61P29/00A61P35/00A61K101/02A61K103/10A61K103/30
Inventor 杨夏王关全卓连刚宋虎廖伟魏洪源杨宇川
Owner INST OF NUCLEAR PHYSICS & CHEM CHINA ACADEMY OF
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