A Versatile Synthetic Route to the Preparation of 15N Heterocycles | Sciact - CRIS-system of Boreskov Institute of Catalysis

A Versatile Synthetic Route to the Preparation of 15N Heterocycles Full article

Journal

Journal of Labelled Compounds and Radiopharmaceuticals
ISSN: 0362-4803 , E-ISSN: 1099-1344

Output data

Year: 2019, Volume: 62, Number: 13, Pages: 892-902 Pages count : 11 DOI: 10.1002/jlcr.3699

Tags

15N; Contrast Agent; Hyperpolarization; MRI; PHIP; Parahydrogen; pyridine

Authors

Chukanov Nikita V. ^1,2 , Kidd Bryce M. ³ , Kovtunova Larisa M. ^2,4 , Bukhtiyarov Valerii I. ⁴ , Shchepin Roman V. ⁵ , Chekmenev Eduard Y. ^5,7,8 , Goodson Boyd M. ^3,6 , Kovtunov Kirill V. ^1,2 , Koptyug Igor V. ^1,2

Affiliations

1	International Tomography Center SB RAS, Novosibirsk, Russia
2	Novosibirsk State University, Novosibirsk, Russia
3	Department of Chemistry and Biochemistry, Southern Illinois University, Carbondale, IL 62901, USA
4	Boreskov Institute of Catalysis SB RAS, Novosibirsk, Russia
5	Department of Biomedical Engineering and Physics, Vanderbilt-Ingram Cancer Center (VICC), Vanderbilt Institute of Imaging Science (VUIIS), Department of Radiology, Vanderbilt University Medical Center, Nashville, TN, USA
6	Materials Technology Center, Southern Illinois University, Carbondale, IL, USA
7	Russian Academy of Sciences, Moscow, Russia
8	Ibio, Department of Chemistry, Wayne State University, Karmanos Cancer Center, Detroit, MI, USA.

Funding (10)

1	Russian Science Foundation	17-73-20030
2	National Science Foundation	CHE-1416268
3	National Institutes of Health	1R21EB018014
4	National Institutes of Health	1R21EB020323
5	United States Department of Defense	W81XWH-12-1-0159/BC112431
6	United States Department of Defense	W81XWH-15-1-0271
7	United States Department of Defense	W81XWH-15-1-0272
8	National Science Foundation	CHE-1416432
9	National Institutes of Health	1R21CA220137
10	ExxonMobil

A robust medium‐scale (~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 ~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 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 a MRI scanner, respectively. 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.

Chukanov N.V. , Kidd B.M. , Kovtunova L.M. , Bukhtiyarov V.I. , Shchepin R.V. , Chekmenev E.Y. , Goodson B.M. , Kovtunov K.V. , Koptyug I.V.
A Versatile Synthetic Route to the Preparation of 15N Heterocycles

Journal of Labelled Compounds and Radiopharmaceuticals. 2019. V.62. N13. P.892-902. DOI: 10.1002/jlcr.3699 WOS Scopus РИНЦ AN PMID OpenAlex

Full text from publisher

Submitted:	Oct 18, 2017
Accepted:	Dec 2, 2018
Published online:	Dec 11, 2018
Published print:	Nov 1, 2019

Web of science:	WOS:000498736100003
Scopus:	2-s2.0-85059604774
Elibrary:	43206263
Chemical Abstracts:	2019:41987
PMID:	30537260
OpenAlex:	W2905091657

DB	Citing
Scopus	10
Web of science	10
Elibrary	9
OpenAlex	12