Hyperpolarizing Concentrated Metronidazole 15NO2 Group Over Six Chemical Bonds with More Than 15% Polarization and 20 Minute Lifetime.

08:00 EDT 9th April 2019 | BioPortfolio

Summary of "Hyperpolarizing Concentrated Metronidazole 15NO2 Group Over Six Chemical Bonds with More Than 15% Polarization and 20 Minute Lifetime."

NMR hyperpolarization of uniformly 15N-labeled metronidazole-15N3 is demonstrated using SABRE-SHEATH (Signal Amplification by Reversible Exchange in SHield Enables Alignment Transfer to Heteronuclei). In this antibiotic, a 15NO2 group is hyperpolarized via spin relays created by 15N spins in metronidazole-15N3, and the polarization is transferred from parahydrogen-derived hydrides over six chemical bonds. This efficient spin-relayed mechanism of polarization transfer is supported by measurements of polarization dynamics and T1 relaxation in micro-Tesla magnetic fields. In less than a minute of parahydrogen bubbling at ~0.4 µT, a high level of nuclear spin polarization P15N of ~16% is achieved on all three 15N sites of metronidazole-15N3 at up to ~41 mM concentration. This product of 15N polarization and concentration of 15N spins is ~6-fold better than any previous value for 15N SABRE-derived hyperpolarization. At 1.4 T, the hyperpolarized state of the 15NO2 group of this antibiotic persists for tens of minutes (T1~10 min), in part because its 15N spin has no detectable spin-spin couplings with protons of the molecule. A novel synthesis achieving robust uniform 15N enrichment of metronidazole is reported with 15% yield over three steps. This synthetic approach should be suitable for preparation of other 15N-labeled nitroimidazole derivatives, potentially enabling a wide range of in vivo metabolic probes from hypoxia sensing to theranostic imaging.


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Name: Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765


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