A versatile synthetic route to the preparation of 15N heterocycles

Nikita V. Chukanov, Bryce E. Kidd, Larisa M. Kovtunova, Valerii I. Bukhtiyarov, Roman V. Shchepin, Eduard Y. Chekmenev, Boyd M. Goodson, Kirill V. Kovtunov, Igor V. Koptyug

Результат исследования: Научные публикации в периодических изданияхстатья

1 Цитирования (Scopus)

Аннотация

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.

Язык оригиналаанглийский
Страницы (с-по)892-902
Число страниц11
ЖурналJournal of Labelled Compounds and Radiopharmaceuticals
Том62
Номер выпуска13
DOI
СостояниеОпубликовано - 1 ноя 2019

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