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Hydroxyphenyl cross-linked macromolecular network and applications thereof

A technology of macromolecules and hydroxybenzene, which is applied in the cross-linked macromolecular network of hydroxybenzene and its application fields, and can solve the problems of unstable results and the like

Inactive Publication Date: 2007-10-10
THE CLEVELAND CLINIC FOUND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chondrocytes must be introduced into the matrix after matrix formation, with variable and often poor results

Method used

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  • Hydroxyphenyl cross-linked macromolecular network and applications thereof
  • Hydroxyphenyl cross-linked macromolecular network and applications thereof
  • Hydroxyphenyl cross-linked macromolecular network and applications thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0161] The experimental dosage of the tyramine-substituted hyaluronic acid hydrogel with dityramine crosslinking of the present invention was prepared according to the following method. HA was dissolved in 250 mM 2-(N-morpholine)ethanesulfonic acid (MES), 150 mM NaCl, 75 mM NaOH, pH 6.5 at a concentration of 1 mg / ml based on hexuronic acid, and the solution contained relative to HA carboxyl groups The molar concentration of the groups is 10-fold excess of tyramide. Tyramide substitution on the starting carboxyl groups of EDC was subsequently added in a 10-fold excess relative to the molar concentration of HA carboxyl groups. N-hydroxysuccinimide (NHS) was added to the reaction at a molar ratio of 1 / 10 relative to the molar amount of EDC to assist the EDC-catalyzed amidation reaction by forming an activated ester. The reaction was carried out at room temperature for 24 hours, followed by extensive dialysis against 150 mM NaCl followed by ultrapure water followed by lyophilizat...

Embodiment 2

[0163] Experiments were performed to determine the extent of tyramide substitution (and subsequent dityramide crosslinking) of the T-HA macromolecular network of the present invention. First, 3 formulations of (uncrosslinked) tyramide-substituted hyaluronic acid (T-HA) were prepared according to the method described above, named OX, 1X or 10X. OX formulations were prepared without EDC (i.e. no carbodiimides), meaning no carbodiimides were present to mediate tyramine NH 2 group and HA molecule CO 2 A reaction between H groups to form an amide bond. Therefore, the OX formulation can be considered as a control. The 1X formulation contains CO on the HA molecule in the reaction mixture 2 The stoichiometric ratio of the amount of H groups is 1:1 for EDC. The 10X formulation contains CO on the HA molecule in the reaction mixture 2 The stoichiometric ratio of the amount of H groups is 10:1 (or 10-fold excess) of EDC. In all three formulations, the stoichiometric excess of tyrami...

Embodiment 3

[0170] Traditionally, it has been believed that natural cartilage is viscoelastic and is mainly due to the presence of negatively charged SO on adjacent chondroitin sulfate chains in the aggrecan matrix. 4 2- Due to the repulsive forces between the groups, natural cartilage is able to resist deformation and absorb compressive loads. Tests are carried out to determine that the macromolecular network that only contains dityramide cross-linked hyaluronic acid molecules (i.e. no aggrecan and chondroitin sulfate) in the present invention has no SO 4 2- Efficacy in resisting deformation and absorbing pressure in the case of cartilage compared with natural cartilage. Specifically, three kinds of networks were prepared respectively: 1) HA molecules cross-linked by dityramine (T-HA); 2) chondroitin sulfate in the form of proteoglycans cross-linked by dityramide (T-Aggrecan); and 3) A composite material composed of 50% T-HA and 50% T-Aggrecan. An uncrosslinked T-HA formulation with ...

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Abstract

A dihydroxyphenyl cross-linked macromolecular network is provided that is useful in artificial tissue and tissue engineering applications, particularly to provide a synthetic, implantable tissue matrix material for a wide variety of tissue types. In particular, artificial or synthetic cartilage, vocal cord material, vitreous material, soft tissue material and mitral valve material are described. In an embodiment, the network is composed of tyramine-substituted and cross-linked hyaluronan molecules, wherein cross-linking is achieved via peroxidase-mediated dityramine-linkages that can be performed in vivo. The dityramine bonds provide a stable, coherent hyaluronan-based hydrogel with desired physical properties.

Description

[0001] This patent application claims priority to US Provisional Patent Application No. 60 / 586,585, filed July 9, 2004, which is hereby incorporated in its entirety as a part of this application. Background technique [0002] Articular cartilage performs essential functions in healthy joints. Articular cartilage absorbs and distributes impact and friction loads thereby transferring these loads away from the bone and protecting it from injury. Cartilage does this by transferring load forces to a fluid phase within a three-dimensional network of aggrecan molecules (described in the next section) confined within the joint space. The aggrecan molecule contains up to 100 chondroitin sulfate (CS) chains connected to the core protein, and multiple electronegative sulfate groups are distributed along the entire length of each chondroitin sulfate chain. These sulfate groups cause mutual repulsion between the individual chondroitin sulfate chains on a single aggrecan molecule (causing ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08L89/00C08G63/48C08G63/91
CPCA61L27/20A61K9/0024A61K47/36A61L27/14A61L27/50
Inventor 安东尼・卡拉布罗李・阿克斯特丹尼尔・阿拉姆詹姆斯・陈阿尼克・B・达尔深町清隆理查德・A・格罗斯大卫・海恩斯蒲原庆滋丹尼尔・P・诺特伊莱尔・李维斯艾里克斯・梅拉穆德安东尼・米尼亚奇马歇尔・斯特罗梅
Owner THE CLEVELAND CLINIC FOUND
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