Application of 15N2-Diazirines as a Versatile Platform for Hyperpolarization of Biological Molecules by d-DNP

Bioconjug Chem. 2020 Mar 18;31(3):537-541. doi: 10.1021/acs.bioconjchem.0c00028. Epub 2020 Feb 14.

Abstract

15N2-Diazirines represent an attractive class of imaging tags for hyperpolarized magnetic resonance imaging (HP-MRI), offering desirable biocompatibility, ease of incorporation into a variety of molecules, and ability to deliver long-lasting polarization. We have recently established hyperpolarization of 15N2-diazirines in organic solvents using SABRE-Shield Enables Alignment Transfer to Heteronuclei (SABRE-SHEATH). Yet, the current challenge of SABRE-SHEATH in water, specifically poor polarization efficiency, presents a barrier in examining the practical use of 15N2-diazirines for HP-MRI. Herein, we show that efficient polarization of diverse 15N2-diazirine-labeled molecules in water can be readily achieved by dissolution dynamic nuclear polarization (d-DNP), a hyperpolarization technique used in clinical practice. Hyperpolarization by d-DNP also demonstrates greater enhancement for long-lasting 15N signals, in comparison with SABRE-SHEATH. Various biologically important molecules are studied in this work, including amino acid, sugar, and drug compounds, demonstrating the great potential of 15N2-diazirines as molecular tags in broad biomedical and clinical applications.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Diazomethane / chemistry*
  • Magnetic Resonance Imaging / methods*
  • Nitrogen Isotopes / chemistry*

Substances

  • Nitrogen Isotopes
  • Nitrogen-15
  • Diazomethane