Metal ion-mediated nitric oxide generation from polyurethanes via covalently linked copper(II)-cyclen moieties.

Polyurethanes are widely used in the manufacturing of biomedical catheters and other blood-contacting devices; however, thrombus formation still occurs, which renders these catheters ineffective unless systemic anticlotting agents are used. Nitric oxide (NO) is a well-known inhibitor of platelet activity. In the current study, two commercially available medical polyurethanes (Pellethane and Tecophilic) were derivatized to possess NO-generating Cu(II)-cyclen moieties pendant to the polymer backbone. A new three-step synthetic approach is used, that is simpler than a recently reported method to prepare Cu(II)-cyclen-polyurethane materials. Both derivatized polyurethanes were found to produce NO at levels at or above those of endothelial cells. A comparison between the modified commercial polyurethanes (hydrophobic vs. hydrophilic) is presented, including the synthetic scheme, extensive characterization, and coating application. These derivatized polymers may serve as useful coatings to prevent clotting on the surface of catheters and other blood-contacting biomedical devices.