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

Roman V. Shchepin, Jonathan R. Birchall, Nikita V. Chukanov, Kirill V. Kovtunov, Igor V. Koptyug, Thomas Theis, Warren S. Warren, Juri G. Gelovani, Boyd M. Goodson, Sepideh Shokouhi, Matthew S. Rosen, Yi Fen Yen, Wellington Pham, Eduard Y. Chekmenev

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15 Citations (Scopus)

Abstract

The NMR hyperpolarization of uniformly 15N-labeled [15N3]metronidazole is demonstrated by using SABRE-SHEATH. In this antibiotic, the 15NO2 group is hyperpolarized through spin relays created by 15N spins in [15N3]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 15N sites. This product of 15N polarization and concentration of 15N spins is around six-fold better than any previous value determined for 15N 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 15N-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.

Original languageEnglish
Pages (from-to)8829-8836
Number of pages8
JournalChemistry - A European Journal
Volume25
Issue number37
DOIs
Publication statusPublished - 2 Jul 2019

Keywords

  • hyperpolarization
  • isotopic labeling
  • nitrogen heterocycles
  • NMR spectroscopy
  • SABRE
  • spin relays
  • NMR SIGNAL AMPLIFICATION
  • PARA-HYDROGEN
  • SPIN DYNAMICS
  • SENSITIVITY
  • TO-NOISE RATIO
  • PARAHYDROGEN
  • REVERSIBLE EXCHANGE
  • N-15 HYPERPOLARIZATION
  • MAGNETIC-RESONANCE

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