Diazirines as Potential Molecular Imaging Tags: Probing the Requirements for Efficient and Long-Lived SABRE-Induced Hyperpolarization

Angew Chem Int Ed Engl. 2017 Sep 25;56(40):12112-12116. doi: 10.1002/anie.201704970. Epub 2017 Jul 24.

Abstract

Diazirines are an attractive class of potential molecular tags for magnetic resonance imaging owing to their biocompatibility and ease of incorporation into a large variety of molecules. As recently reported, 15 N2 -diazirine can be hyperpolarized by the SABRE-SHEATH method, sustaining both singlet and magnetization states, thus offering a path to long-lived polarization storage. Herein, we show the generality of this approach by illustrating that the diazirine tag alone is sufficient for achieving excellent signal enhancements with long-lasting polarization. Our investigations reveal the critical role of Lewis basic additives, including water, on achieving SABRE-promoted hyperpolarization. The application of this strategy to a 15 N2 -diazirine-containing choline derivative demonstrates the potential of 15 N2 -diazirines as molecular imaging tags for biomedical applications.

Keywords: diazirine; hyperpolarization; imaging agents; iridium; structure-activity relationships.

Publication types

  • Research Support, Non-U.S. Gov't