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

Publication ,  Journal Article
Shchepin, RV; Birchall, JR; Chukanov, NV; Kovtunov, KV; Koptyug, IV; Theis, T; Warren, WS; Gelovani, JG; Goodson, BM; Shokouhi, S; Rosen, MS ...
Published in: Chemistry (Weinheim an der Bergstrasse, Germany)
July 2019

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.

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Published In

Chemistry (Weinheim an der Bergstrasse, Germany)

DOI

EISSN

1521-3765

ISSN

0947-6539

Publication Date

July 2019

Volume

25

Issue

37

Start / End Page

8829 / 8836

Related Subject Headings

  • General Chemistry
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

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Shchepin, R. V., Birchall, J. R., Chukanov, N. V., Kovtunov, K. V., Koptyug, I. V., Theis, T., … Chekmenev, E. Y. (2019). Hyperpolarizing Concentrated Metronidazole 15 NO2 Group over Six Chemical Bonds with More than 15 % Polarization and a 20 Minute Lifetime. Chemistry (Weinheim an Der Bergstrasse, Germany), 25(37), 8829–8836. https://doi.org/10.1002/chem.201901192
Shchepin, Roman V., Jonathan R. Birchall, Nikita V. Chukanov, Kirill V. Kovtunov, Igor V. Koptyug, Thomas Theis, Warren S. Warren, et al. “Hyperpolarizing Concentrated Metronidazole 15 NO2 Group over Six Chemical Bonds with More than 15 % Polarization and a 20 Minute Lifetime.Chemistry (Weinheim an Der Bergstrasse, Germany) 25, no. 37 (July 2019): 8829–36. https://doi.org/10.1002/chem.201901192.
Shchepin RV, Birchall JR, Chukanov NV, Kovtunov KV, Koptyug IV, Theis T, et al. Hyperpolarizing Concentrated Metronidazole 15 NO2 Group over Six Chemical Bonds with More than 15 % Polarization and a 20 Minute Lifetime. Chemistry (Weinheim an der Bergstrasse, Germany). 2019 Jul;25(37):8829–36.
Shchepin, Roman V., et al. “Hyperpolarizing Concentrated Metronidazole 15 NO2 Group over Six Chemical Bonds with More than 15 % Polarization and a 20 Minute Lifetime.Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 25, no. 37, July 2019, pp. 8829–36. Epmc, doi:10.1002/chem.201901192.
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. Hyperpolarizing Concentrated Metronidazole 15 NO2 Group over Six Chemical Bonds with More than 15 % Polarization and a 20 Minute Lifetime. Chemistry (Weinheim an der Bergstrasse, Germany). 2019 Jul;25(37):8829–8836.
Journal cover image

Published In

Chemistry (Weinheim an der Bergstrasse, Germany)

DOI

EISSN

1521-3765

ISSN

0947-6539

Publication Date

July 2019

Volume

25

Issue

37

Start / End Page

8829 / 8836

Related Subject Headings

  • General Chemistry
  • 34 Chemical sciences
  • 03 Chemical Sciences