Heparin–polynitroxides: Synthesis and preliminary evaluation as cardiovascular EPR/MR imaging probes and extracellular space-targeted antioxidants

We report here the synthesis of heparin–polynitroxide derivatives (HPNs) in which nitroxide moieties are linked either to uronic acid or glycosamine residues of the heparin macromolecule. HPNs have low anticoagulant activity, possess superoxide scavenging properties, bind to the vascular endothelium/extra-cellular matrix and can be detected by EPR and MRI techniques. As the vascular wall-targeted redox-active paramagnetic compounds, HPNs may have both diagnostic (molecular MRI) and therapeutic (ecSOD mimics) applications.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Three novel heparin–polynitroxide derivatives were synthesized. ► They exhibit low anticoagulant activity and posses superoxide scavenging properties. ► They bind to vascular endothelium and have long in vivo life time. ► They can be detected in the vascular wall by EPR and MRI techniques. ► They may become a platform for the creation of new diagnostic and therapeutic agents.