Tailored synthesis of nitric oxide-releasing polyurethanes using O2-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

doi:10.1039/C000152J

Tailored synthesis of nitric oxide-releasing polyurethanes using O²-protected diazeniumdiolated chain extenders†

Melissa M. Reynolds,^a Joseph E. Saavedra,^b Brett M. Showalter,^c Carlos A. Valdez,^c Anna P. Shanklin,^c Bong K. Oh,^a Larry K. Keefer^c and Mark E. Meyerhoff*^a

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^a Department of Chemistry, The University of Michigan, 930 North University Avenue, Ann Arbor, MI, USA
E-mail: mmeyerho@umich.edu
Fax: +1 734-647-4865
Tel: +1 734-763-5916

^b Basic Science Program, SAIC Frederick, National Cancer Institute at Frederick, Frederick, Maryland, USA

^c Chemistry Section, Laboratory of Comparative Carcinogenesis, National Cancer Institute at Frederick, Frederick, Maryland, USA

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, the details of a new synthetic approach for preparing NO-releasing diazeniumdiolated polyurethanes (PUs) 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.

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Article information

DOI: https://doi.org/10.1039/C000152J
Article type: Paper
Submitted: 07 Jan 2010
Accepted: 05 Feb 2010
First published: 05 Mar 2010

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J. Mater. Chem., 2010,20, 3107-3114

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Tailored synthesis of nitric oxide-releasing polyurethanes using O²-protected diazeniumdiolated chain extenders

M. M. Reynolds, J. E. Saavedra, B. M. Showalter, C. A. Valdez, A. P. Shanklin, B. K. Oh, L. K. Keefer and M. E. Meyerhoff, J. Mater. Chem., 2010, 20, 3107 DOI: 10.1039/C000152J

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Journal of Materials Chemistry