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Hyperpolarizing Concentrated Metronidazole 15NO2 Group over Six Chemical Bonds with More than 15 % Polarization and a 20 Minute Lifetime. / Shchepin, Roman V.; Birchall, Jonathan R.; Chukanov, Nikita V. et al.

In: Chemistry - A European Journal, Vol. 25, No. 37, 02.07.2019, p. 8829-8836.

Research output: Contribution to journal › Article › peer-review

Harvard

Shchepin, RV, Birchall, JR, Chukanov, NV, Kovtunov, KV, Koptyug, IV, Theis, T, Warren, WS, Gelovani, JG, Goodson, BM, Shokouhi, S, Rosen, MS, Yen, YF, Pham, W & Chekmenev, EY 2019, 'Hyperpolarizing Concentrated Metronidazole 15NO2 Group over Six Chemical Bonds with More than 15 % Polarization and a 20 Minute Lifetime', Chemistry - A European Journal, vol. 25, no. 37, pp. 8829-8836. https://doi.org/10.1002/chem.201901192

APA

Shchepin, R. V., Birchall, J. R., Chukanov, N. V., Kovtunov, K. V., Koptyug, I. V., Theis, T., Warren, W. S., Gelovani, J. G., Goodson, B. M., Shokouhi, S., Rosen, M. S., Yen, Y. F., Pham, W., & Chekmenev, E. Y. (2019). Hyperpolarizing Concentrated Metronidazole 15NO2 Group over Six Chemical Bonds with More than 15 % Polarization and a 20 Minute Lifetime. Chemistry - A European Journal, 25(37), 8829-8836. https://doi.org/10.1002/chem.201901192

Vancouver

Shchepin RV, Birchall JR, Chukanov NV, Kovtunov KV, Koptyug IV, Theis T et al. Hyperpolarizing Concentrated Metronidazole 15NO2 Group over Six Chemical Bonds with More than 15 % Polarization and a 20 Minute Lifetime. Chemistry - A European Journal. 2019 Jul 2;25(37):8829-8836. doi: 10.1002/chem.201901192

Author

Shchepin, Roman V. ; Birchall, Jonathan R. ; Chukanov, Nikita V. et al. / Hyperpolarizing Concentrated Metronidazole 15NO2 Group over Six Chemical Bonds with More than 15 % Polarization and a 20 Minute Lifetime. In: Chemistry - A European Journal. 2019 ; Vol. 25, No. 37. pp. 8829-8836.

BibTeX

@article{5fcf1f38406544e9860f5b79bfe700ff,
title = "Hyperpolarizing Concentrated Metronidazole 15NO2 Group over Six Chemical Bonds with More than 15 % Polarization and a 20 Minute Lifetime",
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.",
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",
author = "Shchepin, {Roman V.} and Birchall, {Jonathan R.} and Chukanov, {Nikita V.} and Kovtunov, {Kirill V.} and Koptyug, {Igor V.} and Thomas Theis and Warren, {Warren S.} and Gelovani, {Juri G.} and Goodson, {Boyd M.} and Sepideh Shokouhi and Rosen, {Matthew S.} and Yen, {Yi Fen} and Wellington Pham and Chekmenev, {Eduard Y.}",
note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",
year = "2019",
month = jul,
day = "2",
doi = "10.1002/chem.201901192",
language = "English",
volume = "25",
pages = "8829--8836",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "37",

}

RIS

TY - JOUR

T1 - Hyperpolarizing Concentrated Metronidazole 15NO2 Group over Six Chemical Bonds with More than 15 % Polarization and a 20 Minute Lifetime

AU - Shchepin, Roman V.

AU - Birchall, Jonathan R.

AU - Chukanov, Nikita V.

AU - Kovtunov, Kirill V.

AU - Koptyug, Igor V.

AU - Theis, Thomas

AU - Warren, Warren S.

AU - Gelovani, Juri G.

AU - Goodson, Boyd M.

AU - Shokouhi, Sepideh

AU - Rosen, Matthew S.

AU - Yen, Yi Fen

AU - Pham, Wellington

AU - Chekmenev, Eduard Y.

N1 - Publisher Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/7/2

Y1 - 2019/7/2

N2 - 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.

AB - 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.

KW - hyperpolarization

KW - isotopic labeling

KW - nitrogen heterocycles

KW - NMR spectroscopy

KW - SABRE

KW - spin relays

KW - NMR SIGNAL AMPLIFICATION

KW - PARA-HYDROGEN

KW - SPIN DYNAMICS

KW - SENSITIVITY

KW - TO-NOISE RATIO

KW - PARAHYDROGEN

KW - REVERSIBLE EXCHANGE

KW - N-15 HYPERPOLARIZATION

KW - MAGNETIC-RESONANCE

UR - http://www.scopus.com/inward/record.url?scp=85066507911&partnerID=8YFLogxK

U2 - 10.1002/chem.201901192

DO - 10.1002/chem.201901192

M3 - Article

C2 - 30964568

AN - SCOPUS:85066507911

VL - 25

SP - 8829

EP - 8836

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 37

ER -

ID: 20345135