Synthetic Approaches for 15N-Labeled Hyperpolarized Heterocyclic Molecular Imaging Agents for 15N NMR Signal Amplification by Reversible Exchange in Microtesla Magnetic Fields

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Synthetic Approaches for ¹⁵N-Labeled Hyperpolarized Heterocyclic Molecular Imaging Agents for ¹⁵N NMR Signal Amplification by Reversible Exchange in Microtesla Magnetic Fields. / Chukanov, Nikita V.; Shchepin, Roman V.; Joshi, Sameer M. и др.

в: Chemistry - A European Journal, Том 27, № 38, 07.07.2021, стр. 9727-9736.

Результаты исследований: Научные публикации в периодических изданиях › обзорная статья › Рецензирование

BibTeX

@article{70b3d6a945564ee09a98e1069e070d31,

title = "Synthetic Approaches for 15N-Labeled Hyperpolarized Heterocyclic Molecular Imaging Agents for 15N NMR Signal Amplification by Reversible Exchange in Microtesla Magnetic Fields",

abstract = "NMR hyperpolarization techniques enhance nuclear spin polarization by several orders of magnitude resulting in corresponding sensitivity gains. This enormous sensitivity gain enables new applications ranging from studies of small molecules by using high-resolution NMR spectroscopy to real-time metabolic imaging in vivo. Several hyperpolarization techniques exist for hyperpolarization of a large repertoire of nuclear spins, although the 13C and 15N sites of biocompatible agents are the key targets due to their widespread use in biochemical pathways. Moreover, their long T1 allows hyperpolarized states to be retained for up to tens of minutes. Signal amplification by reversible exchange (SABRE) is a low-cost and ultrafast hyperpolarization technique that has been shown to be versatile for the hyperpolarization of 15N nuclei. Although large sensitivity gains are enabled by hyperpolarization, 15N natural abundance is only ∼0.4 %, so isotopic labeling of the molecules to be hyperpolarized is required in order to take full advantage of the hyperpolarized state. Herein, we describe selected advances in the preparation of 15N-labeled compounds with the primary emphasis on using these compounds for SABRE polarization in microtesla magnetic fields through spontaneous polarization transfer from parahydrogen. Also, these principles can certainly be applied for hyperpolarization of these emerging contrast agents using dynamic nuclear polarization and other techniques.",

keywords = "Hyperpolarization, magnetic resonance imaging, NMR spectroscopy, parahydrogen, spectroscopy, Magnetic Resonance Imaging, Magnetic Resonance Spectroscopy, Isotope Labeling, Molecular Imaging, Magnetic Fields",

author = "Chukanov, {Nikita V.} and Shchepin, {Roman V.} and Joshi, {Sameer M.} and Kabir, {Mohammad S.H.} and Salnikov, {Oleg G.} and Alexandra Svyatova and Koptyug, {Igor V.} and Gelovani, {Juri G.} and Chekmenev, {Eduard Y.}",

note = "Funding Information: We thank the following for funding support: NSF CHE‐1904780 (E.Y.C.), NCI 1R21CA220137 (E.Y.C.), NIBIB 1R01EB029829 (E.Y.C.). N.V.C. and A.S. acknowledge financial support from RFBR and the government of the Novosibirsk region (19‐43‐540004). O.G.S. and I.V.K. thank RFBR (grants # 19‐29‐10003 and 19‐53‐12013) for the support of catalyst synthesis, and the Russian Ministry of Science and Higher Education for access to NMR/MRI equipment. Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",

year = "2021",

month = jul,

day = "7",

doi = "10.1002/chem.202100212",

language = "English",

volume = "27",

pages = "9727--9736",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "38",

}

RIS

TY - JOUR

T1 - Synthetic Approaches for 15N-Labeled Hyperpolarized Heterocyclic Molecular Imaging Agents for 15N NMR Signal Amplification by Reversible Exchange in Microtesla Magnetic Fields

AU - Chukanov, Nikita V.

AU - Shchepin, Roman V.

AU - Joshi, Sameer M.

AU - Kabir, Mohammad S.H.

AU - Salnikov, Oleg G.

AU - Svyatova, Alexandra

AU - Koptyug, Igor V.

AU - Gelovani, Juri G.

AU - Chekmenev, Eduard Y.

N1 - Funding Information: We thank the following for funding support: NSF CHE‐1904780 (E.Y.C.), NCI 1R21CA220137 (E.Y.C.), NIBIB 1R01EB029829 (E.Y.C.). N.V.C. and A.S. acknowledge financial support from RFBR and the government of the Novosibirsk region (19‐43‐540004). O.G.S. and I.V.K. thank RFBR (grants # 19‐29‐10003 and 19‐53‐12013) for the support of catalyst synthesis, and the Russian Ministry of Science and Higher Education for access to NMR/MRI equipment. Publisher Copyright: © 2021 Wiley-VCH GmbH Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2021/7/7

Y1 - 2021/7/7

N2 - NMR hyperpolarization techniques enhance nuclear spin polarization by several orders of magnitude resulting in corresponding sensitivity gains. This enormous sensitivity gain enables new applications ranging from studies of small molecules by using high-resolution NMR spectroscopy to real-time metabolic imaging in vivo. Several hyperpolarization techniques exist for hyperpolarization of a large repertoire of nuclear spins, although the 13C and 15N sites of biocompatible agents are the key targets due to their widespread use in biochemical pathways. Moreover, their long T1 allows hyperpolarized states to be retained for up to tens of minutes. Signal amplification by reversible exchange (SABRE) is a low-cost and ultrafast hyperpolarization technique that has been shown to be versatile for the hyperpolarization of 15N nuclei. Although large sensitivity gains are enabled by hyperpolarization, 15N natural abundance is only ∼0.4 %, so isotopic labeling of the molecules to be hyperpolarized is required in order to take full advantage of the hyperpolarized state. Herein, we describe selected advances in the preparation of 15N-labeled compounds with the primary emphasis on using these compounds for SABRE polarization in microtesla magnetic fields through spontaneous polarization transfer from parahydrogen. Also, these principles can certainly be applied for hyperpolarization of these emerging contrast agents using dynamic nuclear polarization and other techniques.

AB - NMR hyperpolarization techniques enhance nuclear spin polarization by several orders of magnitude resulting in corresponding sensitivity gains. This enormous sensitivity gain enables new applications ranging from studies of small molecules by using high-resolution NMR spectroscopy to real-time metabolic imaging in vivo. Several hyperpolarization techniques exist for hyperpolarization of a large repertoire of nuclear spins, although the 13C and 15N sites of biocompatible agents are the key targets due to their widespread use in biochemical pathways. Moreover, their long T1 allows hyperpolarized states to be retained for up to tens of minutes. Signal amplification by reversible exchange (SABRE) is a low-cost and ultrafast hyperpolarization technique that has been shown to be versatile for the hyperpolarization of 15N nuclei. Although large sensitivity gains are enabled by hyperpolarization, 15N natural abundance is only ∼0.4 %, so isotopic labeling of the molecules to be hyperpolarized is required in order to take full advantage of the hyperpolarized state. Herein, we describe selected advances in the preparation of 15N-labeled compounds with the primary emphasis on using these compounds for SABRE polarization in microtesla magnetic fields through spontaneous polarization transfer from parahydrogen. Also, these principles can certainly be applied for hyperpolarization of these emerging contrast agents using dynamic nuclear polarization and other techniques.

KW - Hyperpolarization

KW - magnetic resonance imaging

KW - NMR spectroscopy

KW - parahydrogen

KW - spectroscopy

KW - Magnetic Resonance Imaging

KW - Magnetic Resonance Spectroscopy

KW - Isotope Labeling

KW - Molecular Imaging

KW - Magnetic Fields

UR - http://www.scopus.com/inward/record.url?scp=85105905816&partnerID=8YFLogxK

U2 - 10.1002/chem.202100212

DO - 10.1002/chem.202100212

M3 - Review article

C2 - 33856077

AN - SCOPUS:85105905816

VL - 27

SP - 9727

EP - 9736

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 38

ER -

ID: 28874350