Heterogeneous 1H and 13C Parahydrogen‐Induced Polarization of Acetate and Pyruvate Esters | Sciact - CRIS-system of Boreskov Institute of Catalysis

Heterogeneous 1H and 13C Parahydrogen‐Induced Polarization of Acetate and Pyruvate Esters Full article

Journal

ChemPhysChem
ISSN: 1439-4235 , E-ISSN: 1439-7641

Output data

Year: 2021, Volume: 22, Number: 12, Pages: 1389-1396 Pages count : 8 DOI: 10.1002/cphc.202100156

Tags

parahydrogen; Hyperpolarization; PHIP; NMR spectroscopy; imaging agents

Authors

Salnikov Oleg G. ^1,2,3 , Chukanov Nikita V. ^1,3 , Kovtunova Larisa M. ^1,2,3 , Bukhtiyarov Valerii I. ^2,3 , Kovtunov Kirill V. ^1,3 , Shchepin Roman V. ⁴ , Koptyug Igor V. ¹ , Chekmenev Eduard Y. ^5,6

Affiliations

1	International Tomography Center SB RAS, 3A Institutskaya St., 630090 Novosibirsk, Russia
2	Boreskov Institute of Catalysis SB RAS, 5 Acad. Lavrentiev Pr., 630090 Novosibirsk, Russia
3	Department of Natural Sciences, Novosibirsk State University, 2 Pirogova St., 630090 Novosibirsk, Russia
4	Department of Chemistry, Biology, and Health Sciences, South Dakota School of Mines & Technology, Rapid City, South Dakota 57701, United States
5	Department of Chemistry, Integrative Biosciences (Ibio), Karmanos Cancer Institute (KCI), Wayne State University, Detroit, Michigan 48202, United States
6	Russian Academy of Sciences, 14 Leninskiy Prospekt, 119991 Moscow, Russia

Funding (8)

1	Russian Foundation for Basic Research	19-29-10003 (АААА-А19-119100890052-8)
2	Russian Foundation for Basic Research	19-43-540004 (АААА-А19-119090590009-9)
3	Russian Foundation for Basic Research	19-33-60045
4	Ministry of Science and Higher Education of the Russian Federation	0239-2021-0002
5	National Science Foundation	CHE-1904780
6	National Institutes of Health	1R21CA220137
7	National Institutes of Health	1R21HL154032-01
8	United States Department of Defense	W81XWH-12-1-0159/BC112431

Magnetic resonance imaging of [1‐ 13 C]hyperpolarized carboxylates (most notably, [1‐ 13 C]pyruvate) allows one to visualize abnormal metabolism in tumors and other pathologies. Here we investigate the efficiency of 1 H and 13 C hyperpolarization of acetate and pyruvate esters with ethyl, propyl and allyl alcoholic moieties using heterogeneous hydrogenation of corresponding vinyl, allyl and propargyl precursors in isotopically unlabeled and 1‐ 13 C‐enriched forms with parahydrogen over Rh/TiO 2 catalysts in methanol‐d 4 and in D 2 O. The maximum obtained 1 H polarization was 0.6 ± 0.2% (for propyl acetate in CD 3 OD), while the highest 13 C polarization was 0.10 ± 0.03% (for ethyl acetate in CD 3 OD). Hyperpolarization of acetate esters surpassed that of pyruvates, while esters with a triple carbon‐carbon bond in unsaturated alcoholic moiety were less efficient as parahydrogen‐induced polarization precursors than esters with a double bond. Among the compounds studied, the maximum 1 H and 13 C NMR signal intensities were observed for propyl acetate. Ethyl acetate yielded slightly less intense NMR signals which were dramatically greater than those of other esters under study.

Salnikov O.G. , Chukanov N.V. , Kovtunova L.M. , Bukhtiyarov V.I. , Kovtunov K.V. , Shchepin R.V. , Koptyug I.V. , Chekmenev E.Y.
Heterogeneous 1H and 13C Parahydrogen‐Induced Polarization of Acetate and Pyruvate Esters
ChemPhysChem. 2021. V.22. N12. P.1389-1396. DOI: 10.1002/cphc.202100156 WOS Scopus РИНЦ AN PMID OpenAlex

Submitted:	Feb 26, 2021
Accepted:	Apr 30, 2021
Published online:	Apr 30, 2021
Published print:	Jul 2, 2021

Web of science:	WOS:000655533000001
Scopus:	2-s2.0-85106652401
Elibrary:	46085696
Chemical Abstracts:	2021:1189529
PMID:	33929077
OpenAlex:	W3158727826

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