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Hydrophobic polysaccharides with pendent groups having terminal reactive functionalities and medical uses thereof

a technology of reactive functionalities and hydrophobic polysaccharides, which is applied in the field of hydrophobic derivatives of polysaccharides, can solve the problems of difficult to keep a coated hydrophobic (14)glucopyranose polymer stably, and difficulty in forming a matrix, so as to promote non-enzymatic hydrolysis, reduce the hydrophobicity of the matrix, and increase the susceptibility of the (14)glucopy

Inactive Publication Date: 2012-03-01
SURMODICS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention relates to hydrophobic derivatives of natural biodegradable polysaccharides that can be used in implantable or injectable medical devices. The invention provides a hydrophobic α(1→4)glucopyranose polymer with pendent groups that have a hydroxyl or amine group at a termus, which improves its use in various medical applications. The hydroxyl or amine group can be used to bond the polymer to other materials, such as a device surface or another polymer, to create a stable matrix. The presence of these groups also makes the polymer more compatible with the human body, as they provide improved attachment to the device surface. The invention also provides a method for modifying the polymer to include additional pendent groups with hydroxyl or amine groups for crosslinking with other materials. The resulting polymeric matrices have improved properties, such as thickness, adhesion, and compliance.

Problems solved by technology

It has been found, in certain cases, that the hydrophobicity of a hydrophobic α(1→4)glucopyranose polymer makes it difficult to form a matrix that is stably associated with another material surface.
For example, it can be difficult to keep a coated hydrophobic α(1→4)glucopyranose polymer stably associated with certain surfaces of an implantable device.

Method used

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  • Hydrophobic polysaccharides with pendent groups having terminal reactive functionalities and medical uses thereof
  • Hydrophobic polysaccharides with pendent groups having terminal reactive functionalities and medical uses thereof
  • Hydrophobic polysaccharides with pendent groups having terminal reactive functionalities and medical uses thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0146]As shown in the reaction scheme below, maltodextrin is dissolved into dimethylsulfoxide (DMSO) and stirred magnetically until fully dissolved at room temperature. N-Boc-Alanine is dissolved into an aliquot of DMSO, with an equivalent of N,N′-diisopropylcarbodiimide (CDI). This solution is premixed for 30 minutes and then added to the solution of maltodextrin. The catalyst, 4-(dimethylamino)pyridine (DMAP) is added to the final solution to enhance the esterification reaction. The coupling proceeds for 2 hours. The protected amino acid-modified polysaccharide can be purified using dialysis in deionized water in SpectraPor dialysis tubing. Lyophilization will yield the dried polymer. The t-butylcarboxyl (Boc) protecting group can be removed with acid hydrolysis using hydrochloric acid in methanol in an organic solvent. The final polymer can be dialyzed again to remove the cleaved protecting group and solvents, followed by lyophilization to achieve the final modified polysaccharid...

example 2

[0147]As shown in the reaction scheme below, maltodextrin is dissolved into dimethylsulfoxide (DMSO) and stirred magnetically until fully dissolved at room temperature. N-Boc-threonine is dissolved into an aliquot of DMSO, with an equivalent of N,N′-diisopropylcarbodiimide (CDI). This solution is premixed for 30 minutes and then added to the solution of maltodextrin. The catalyst, 4-(dimethylamino)pyridine (DMAP) is added to the final solution to enhance the esterification reaction. The coupling proceeds for 2 hours. The protected amino acid-modified polysaccharide can be purified using dialysis in deionized water in SpectraPor dialysis tubing. Lyophilization will yield the dried polymer. The t-butylcarboxyl (Boc) protecting group can be removed with acid hydrolysis using hydrochloric acid in methanol in an organic solvent. The final polymer can be dialyzed again to remove the cleaved protecting group and solvents, followed by lyophilization to achieve the final modified polysacchar...

example 3

[0148]As shown in the reaction scheme below, maltodextrin is dissolved into dimethylsulfoxide (DMSO) and stirred magnetically until fully dissolved at room temperature. N-Boc-ε-caprolactam is added to the DMSO solution, along with an equivalent of a non-nucleophilic base, such as N-methylmorpholine (NMM). This solution is allowed to react for 120 minutes. The caprolactam-modified polysaccharide can be purified using dialysis in deionized water in SpectraPor dialysis tubing. Lyophilization will yield the dried polymer. The t-butylcarboxyl (Boc) protecting group can be removed with acid hydrolysis using hydrochloric acid in methanol in an organic solvent. The final polymer can be dialyzed again to remove the cleaved protecting group and solvents, followed by lyophilization to achieve the final modified polysaccharide.

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Abstract

Hydrophobic α(1→4)glucopyranose polymers useful for the preparation of implantable or injectable medical articles are described. The hydrophobic α(1→4)glucopyranose polymer includes pendent groups having hydrocarbon groups and terminal amine or hydroxyl groups. Biodegradable matrices can be formed from these polymers, and the matrices can be used for the preparation of implantable and injectable medical devices wherein the matrix is capable of degrading in vivo. Matrices including and capable of releasing a bioactive agent in vivo are also described.

Description

PRIORITY CLAIM[0001]This application claims the benefit of U.S. Provisional Patent Application Ser. No. 61 / 291,172, filed Dec. 30, 2009, entitled HYDROPHOBIC POLYSACCHARIDES WITH PENDENT GROUPS HAVING TERMINAL REACTIVE FUNCTIONALITIES, the disclosure of which is incorporated herein by reference.TECHNICAL FIELD[0002]The present invention relates to hydrophobic derivatives of polysaccharides, and articles including these derivatives for use within the body.BACKGROUND[0003]Biodegradable polymers have been used to prepare biodegradable polymeric matrices that can be associated with, or formed into, implantable medical devices. For example, biodegradable polymers can be used to make a thin coating on a medical device surface. Such coatings can enhance the function of the device. Biodegradable polymers having thermoplastic properties can even be molded or formed into a shape to provide an implantable device having a structural property useful for treating a medical condition at the site o...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61F13/00C07H1/00
CPCA61L27/20A61L27/58A61L29/043C07H13/04A61L31/042A61L31/148A61L29/148
Inventor ROLFES MEYERING, EMILY R.
Owner SURMODICS INC