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Synthesis and 15N NMR Signal Amplification by Reversible Exchange of [15N]Dalfampridine at Microtesla Magnetic Fields. / Chukanov, Nikita V.; Salnikov, Oleg G.; Trofimov, Ivan A. et al.

In: ChemPhysChem, Vol. 22, No. 10, 17.05.2021, p. 960-967.

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

Harvard

Chukanov, NV, Salnikov, OG, Trofimov, IA, Kabir, MSH, Kovtunov, KV, Koptyug, IV & Chekmenev, EY 2021, 'Synthesis and 15N NMR Signal Amplification by Reversible Exchange of [15N]Dalfampridine at Microtesla Magnetic Fields', ChemPhysChem, vol. 22, no. 10, pp. 960-967. https://doi.org/10.1002/cphc.202100109

APA

Chukanov, N. V., Salnikov, O. G., Trofimov, I. A., Kabir, M. S. H., Kovtunov, K. V., Koptyug, I. V., & Chekmenev, E. Y. (2021). Synthesis and 15N NMR Signal Amplification by Reversible Exchange of [15N]Dalfampridine at Microtesla Magnetic Fields. ChemPhysChem, 22(10), 960-967. https://doi.org/10.1002/cphc.202100109

Vancouver

Chukanov NV, Salnikov OG, Trofimov IA, Kabir MSH, Kovtunov KV, Koptyug IV et al. Synthesis and 15N NMR Signal Amplification by Reversible Exchange of [15N]Dalfampridine at Microtesla Magnetic Fields. ChemPhysChem. 2021 May 17;22(10):960-967. Epub 2021 Mar 18. doi: 10.1002/cphc.202100109

Author

Chukanov, Nikita V. ; Salnikov, Oleg G. ; Trofimov, Ivan A. et al. / Synthesis and 15N NMR Signal Amplification by Reversible Exchange of [15N]Dalfampridine at Microtesla Magnetic Fields. In: ChemPhysChem. 2021 ; Vol. 22, No. 10. pp. 960-967.

BibTeX

@article{98831ffc593e48dc8a8f363b9d829bb6,
title = "Synthesis and 15N NMR Signal Amplification by Reversible Exchange of [15N]Dalfampridine at Microtesla Magnetic Fields",
abstract = "Signal Amplification by Reversible Exchange (SABRE) technique enables nuclear spin hyperpolarization of wide range of compounds using parahydrogen. Here we present the synthetic approach to prepare 15N-labeled [15N]dalfampridine (4-amino[15N]pyridine) utilized as a drug to reduce the symptoms of multiple sclerosis. The synthesized compound was hyperpolarized using SABRE at microtesla magnetic fields (SABRE-SHEATH technique) with up to 2.0 % 15N polarization. The 7-hour-long activation of SABRE pre-catalyst [Ir(IMes)(COD)Cl] in the presence of [15N]dalfampridine can be remedied by the use of pyridine co-ligand for catalyst activation while retaining the 15N polarization levels of [15N]dalfampridine. The effects of experimental conditions such as polarization transfer magnetic field, temperature, concentration, parahydrogen flow rate and pressure on 15N polarization levels of free and equatorial catalyst-bound [15N]dalfampridine were investigated. Moreover, we studied 15N polarization build-up and decay at magnetic field of less than 0.04 μT as well as 15N polarization decay at the Earth's magnetic field and at 1.4 T.",
keywords = "hyperpolarization, isotopic labeling, NMR spectroscopy, parahydrogen, SABRE",
author = "Chukanov, {Nikita V.} and Salnikov, {Oleg G.} and Trofimov, {Ivan A.} and Kabir, {Mohammad S.H.} and Kovtunov, {Kirill V.} and Koptyug, {Igor V.} and Chekmenev, {Eduard Y.}",
note = "Funding Information: O.G.S.„ K.V.K. and I.V.K. thank the Russian Foundation for Basic Research (grant 19‐53‐12013) and the Russian Ministry of Science and Higher Education (Project AAAA‐A16‐116121510087‐5) for financial support. N.V.C. and I.A.T. acknowledge financial support from the Russian Foundation for Basic Research and Novosibirsk region government (grant 19‐43‐540004) for the synthesis of N‐labeled FAM. N.V.C. thanks Dr. A. I. Taratayko for the useful discussions. E.Y.C. thanks NSF CHE‐1904780 and NIBIB 1R01EB029829. We dedicate this work to the memory of Dr. Kirill V. Kovtunov, our mentor, colleague, and friend. 15 Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",
year = "2021",
month = may,
day = "17",
doi = "10.1002/cphc.202100109",
language = "English",
volume = "22",
pages = "960--967",
journal = "ChemPhysChem",
issn = "1439-4235",
publisher = "Wiley-Blackwell",
number = "10",

}

RIS

TY - JOUR

T1 - Synthesis and 15N NMR Signal Amplification by Reversible Exchange of [15N]Dalfampridine at Microtesla Magnetic Fields

AU - Chukanov, Nikita V.

AU - Salnikov, Oleg G.

AU - Trofimov, Ivan A.

AU - Kabir, Mohammad S.H.

AU - Kovtunov, Kirill V.

AU - Koptyug, Igor V.

AU - Chekmenev, Eduard Y.

N1 - Funding Information: O.G.S.„ K.V.K. and I.V.K. thank the Russian Foundation for Basic Research (grant 19‐53‐12013) and the Russian Ministry of Science and Higher Education (Project AAAA‐A16‐116121510087‐5) for financial support. N.V.C. and I.A.T. acknowledge financial support from the Russian Foundation for Basic Research and Novosibirsk region government (grant 19‐43‐540004) for the synthesis of N‐labeled FAM. N.V.C. thanks Dr. A. I. Taratayko for the useful discussions. E.Y.C. thanks NSF CHE‐1904780 and NIBIB 1R01EB029829. We dedicate this work to the memory of Dr. Kirill V. Kovtunov, our mentor, colleague, and friend. 15 Publisher Copyright: © 2021 Wiley-VCH GmbH Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2021/5/17

Y1 - 2021/5/17

N2 - Signal Amplification by Reversible Exchange (SABRE) technique enables nuclear spin hyperpolarization of wide range of compounds using parahydrogen. Here we present the synthetic approach to prepare 15N-labeled [15N]dalfampridine (4-amino[15N]pyridine) utilized as a drug to reduce the symptoms of multiple sclerosis. The synthesized compound was hyperpolarized using SABRE at microtesla magnetic fields (SABRE-SHEATH technique) with up to 2.0 % 15N polarization. The 7-hour-long activation of SABRE pre-catalyst [Ir(IMes)(COD)Cl] in the presence of [15N]dalfampridine can be remedied by the use of pyridine co-ligand for catalyst activation while retaining the 15N polarization levels of [15N]dalfampridine. The effects of experimental conditions such as polarization transfer magnetic field, temperature, concentration, parahydrogen flow rate and pressure on 15N polarization levels of free and equatorial catalyst-bound [15N]dalfampridine were investigated. Moreover, we studied 15N polarization build-up and decay at magnetic field of less than 0.04 μT as well as 15N polarization decay at the Earth's magnetic field and at 1.4 T.

AB - Signal Amplification by Reversible Exchange (SABRE) technique enables nuclear spin hyperpolarization of wide range of compounds using parahydrogen. Here we present the synthetic approach to prepare 15N-labeled [15N]dalfampridine (4-amino[15N]pyridine) utilized as a drug to reduce the symptoms of multiple sclerosis. The synthesized compound was hyperpolarized using SABRE at microtesla magnetic fields (SABRE-SHEATH technique) with up to 2.0 % 15N polarization. The 7-hour-long activation of SABRE pre-catalyst [Ir(IMes)(COD)Cl] in the presence of [15N]dalfampridine can be remedied by the use of pyridine co-ligand for catalyst activation while retaining the 15N polarization levels of [15N]dalfampridine. The effects of experimental conditions such as polarization transfer magnetic field, temperature, concentration, parahydrogen flow rate and pressure on 15N polarization levels of free and equatorial catalyst-bound [15N]dalfampridine were investigated. Moreover, we studied 15N polarization build-up and decay at magnetic field of less than 0.04 μT as well as 15N polarization decay at the Earth's magnetic field and at 1.4 T.

KW - hyperpolarization

KW - isotopic labeling

KW - NMR spectroscopy

KW - parahydrogen

KW - SABRE

UR - http://www.scopus.com/inward/record.url?scp=85104688462&partnerID=8YFLogxK

U2 - 10.1002/cphc.202100109

DO - 10.1002/cphc.202100109

M3 - Article

C2 - 33738893

AN - SCOPUS:85104688462

VL - 22

SP - 960

EP - 967

JO - ChemPhysChem

JF - ChemPhysChem

SN - 1439-4235

IS - 10

ER -

ID: 28471834