Research output: Contribution to journal › Article › peer-review
A versatile synthetic route to the preparation of 15N heterocycles. / Chukanov, Nikita V.; Kidd, Bryce E.; Kovtunova, Larisa M. et al.
In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 62, No. 13, 01.11.2019, p. 892-902.Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - A versatile synthetic route to the preparation of 15N heterocycles
AU - Chukanov, Nikita V.
AU - Kidd, Bryce E.
AU - Kovtunova, Larisa M.
AU - Bukhtiyarov, Valerii I.
AU - Shchepin, Roman V.
AU - Chekmenev, Eduard Y.
AU - Goodson, Boyd M.
AU - Kovtunov, Kirill V.
AU - Koptyug, Igor V.
N1 - © 2018 John Wiley & Sons, Ltd.
PY - 2019/11/1
Y1 - 2019/11/1
N2 - A robust medium-scale (approximately 3 g) synthetic method for 15N labeling of pyridine (15N-Py) is reported based on the Zincke reaction. 15N enrichment in excess of 81% was achieved with approximately 33% yield. 15N-Py serves as a standard substrate in a wide range of studies employing a hyperpolarization technique for efficient polarization transfer from parahydrogen to heteronuclei; this technique, called SABRE (signal amplification by reversible exchange), employs a simultaneous chemical exchange of parahydrogen and a to-be-hyperpolarized substrate (e.g., pyridine) on metal centers. In studies aimed at the development of hyperpolarized contrast agents for in vivo molecular imaging, pyridine is often employed either as a model substrate (for hyperpolarization technique development, quality assurance, and phantom imaging studies) or as a co-substrate to facilitate more efficient hyperpolarization of a wide range of emerging contrast agents (e.g., nicotinamide). Here, the produced 15N-Py was used for the feasibility study of spontaneous 15N hyperpolarization at high magnetic (HF) fields (7 T and 9.4 T) of an NMR spectrometer and an MRI scanner. SABRE hyperpolarization enabled acquisition of 2D MRI imaging of catalyst-bound 15N-pyridine with 75 × 75 mm2 field of view (FOV), 32 × 32 matrix size, demonstrating the feasibility of 15N HF-SABRE molecular imaging with 2.4 × 2.4 mm2 spatial resolution.
AB - A robust medium-scale (approximately 3 g) synthetic method for 15N labeling of pyridine (15N-Py) is reported based on the Zincke reaction. 15N enrichment in excess of 81% was achieved with approximately 33% yield. 15N-Py serves as a standard substrate in a wide range of studies employing a hyperpolarization technique for efficient polarization transfer from parahydrogen to heteronuclei; this technique, called SABRE (signal amplification by reversible exchange), employs a simultaneous chemical exchange of parahydrogen and a to-be-hyperpolarized substrate (e.g., pyridine) on metal centers. In studies aimed at the development of hyperpolarized contrast agents for in vivo molecular imaging, pyridine is often employed either as a model substrate (for hyperpolarization technique development, quality assurance, and phantom imaging studies) or as a co-substrate to facilitate more efficient hyperpolarization of a wide range of emerging contrast agents (e.g., nicotinamide). Here, the produced 15N-Py was used for the feasibility study of spontaneous 15N hyperpolarization at high magnetic (HF) fields (7 T and 9.4 T) of an NMR spectrometer and an MRI scanner. SABRE hyperpolarization enabled acquisition of 2D MRI imaging of catalyst-bound 15N-pyridine with 75 × 75 mm2 field of view (FOV), 32 × 32 matrix size, demonstrating the feasibility of 15N HF-SABRE molecular imaging with 2.4 × 2.4 mm2 spatial resolution.
KW - N
KW - contrast agent
KW - hyperpolarization
KW - MRI
KW - parahydrogen
KW - PHIP
KW - pyridine
UR - http://www.scopus.com/inward/record.url?scp=85059604774&partnerID=8YFLogxK
U2 - 10.1002/jlcr.3699
DO - 10.1002/jlcr.3699
M3 - Article
C2 - 30537260
AN - SCOPUS:85059604774
VL - 62
SP - 892
EP - 902
JO - Journal of Labelled Compounds and Radiopharmaceuticals
JF - Journal of Labelled Compounds and Radiopharmaceuticals
SN - 0362-4803
IS - 13
ER -
ID: 18063883