Tailored Synthesis of Nitric Oxide-Releasing Polyurethanes Using O-Protected Diazeniumdiolated Chain Extenders.

Melissa M Reynolds, Joseph E Saavedra, Brett M Showalter, Carlos A Valdez, Anna P Shanklin, Bong K Oh, Larry K Keefer, Mark E Meyerhoff
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引用次数: 0

Abstract

Nitric oxide (NO) has been shown to exhibit significant anti-platelet activity and its release from polymer matrices has been already utilized to increase the biocompatibility of various blood-contacting devices. Herein, details of a new synthetic approach for preparing NO-releasing diazeniumdiolated polyurethanes (PU) are described. The method's utility is demonstrated by the incorporation of methoxymethyl- or sugar-protected pre-formed diazeniumdiolate moieties directly into chain extender diols which are then incorporated into the polyurethane backbone. This approach provides the ability to control the number of diazeniumdiolate groups incorporated into the polymer backbone, and hence the surface flux of NO that can ultimately be liberated from polymeric films prepared from the new PU materials. The method provides a means of covalently attaching diazeniumdiolate groups to polyurethanes in a form that resists dissociation of NO during processing but can be activated for spontaneous NO release via hydrolysis of the carbohydrate or methoxymethyl moieties under basic and acidic conditions, respectively.

Abstract Image

Abstract Image

Abstract Image

使用 O 型保护重氮二醇链延伸剂定制合成释放一氧化氮的聚氨酯。
一氧化氮(NO)已被证明具有显著的抗血小板活性,从聚合物基质中释放一氧化氮已被用于提高各种血液接触设备的生物相容性。本文详细介绍了制备释放一氧化氮的重氮二醇化聚氨酯(PU)的新合成方法。该方法的实用性体现在将甲氧基甲基或糖保护的预成形重氮二醇分子直接加入扩链二元醇中,然后再将其加入聚氨酯骨架中。这种方法可以控制加入聚合物骨架中的重氮二酸酯基团的数量,从而控制最终从新型聚氨酯材料制备的聚合物薄膜中释放出来的 NO 的表面通量。该方法提供了一种将二硫代二氮杂环戊烷基团共价连接到聚氨酯上的方法,这种共价连接的形式可在加工过程中阻止 NO 的解离,但可在碱性和酸性条件下分别通过碳水化合物或甲氧基甲基的水解激活 NO 的自发释放。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
Journal of Materials Chemistry
Journal of Materials Chemistry 工程技术-材料科学:综合
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1.5 months
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