Hyperpolarizing Concentrated Metronidazole 15 NO2 Group over Six Chemical Bonds with More than 15 % Polarization and a 20 Minute Lifetime.

Journal Article (Journal Article)

The NMR hyperpolarization of uniformly 15 N-labeled [15 N3 ]metronidazole is demonstrated by using SABRE-SHEATH. In this antibiotic, the 15 NO2 group is hyperpolarized through spin relays created by 15 N spins in [15 N3 ]metronidazole, and the polarization is transferred from parahydrogen-derived hydrides over six chemical bonds. In less than a minute of parahydrogen bubbling at approximately 0.4 μT, a high level of nuclear spin polarization (P15N ) of around 16 % is achieved on all three 15 N sites. This product of 15 N polarization and concentration of 15 N spins is around six-fold better than any previous value determined for 15 N SABRE-derived hyperpolarization. At 1.4 T, the hyperpolarized state persists for tens of minutes (relaxation time, T1 ≈10 min). A novel synthesis of uniformly 15 N-enriched metronidazole is reported with a yield of 15 %. This approach can potentially be used for synthesis of a wide variety of in vivo metabolic probes with potential uses ranging from hypoxia sensing to theranostic imaging.

Full Text

Duke Authors

Cited Authors

  • Shchepin, RV; Birchall, JR; Chukanov, NV; Kovtunov, KV; Koptyug, IV; Theis, T; Warren, WS; Gelovani, JG; Goodson, BM; Shokouhi, S; Rosen, MS; Yen, Y-F; Pham, W; Chekmenev, EY

Published Date

  • July 2019

Published In

Volume / Issue

  • 25 / 37

Start / End Page

  • 8829 - 8836

PubMed ID

  • 30964568

Pubmed Central ID

  • PMC6658333

Electronic International Standard Serial Number (EISSN)

  • 1521-3765

International Standard Serial Number (ISSN)

  • 0947-6539

Digital Object Identifier (DOI)

  • 10.1002/chem.201901192


  • eng