Heterogeneous 1H and 13C Parahydrogen‐Induced Polarization of Acetate and Pyruvate Esters Full article
Journal |
ChemPhysChem
ISSN: 1439-4235 , E-ISSN: 1439-7641 |
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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 |
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Affiliations |
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Funding (8)
1 | United States Department of Defense | W81XWH-12-1-0159/BC112431 |
2 | National Institutes of Health | 1R21CA220137 |
3 | Russian Foundation for Basic Research | 19-43-540004 (АААА-А19-119090590009-9) |
4 | Russian Foundation for Basic Research | 19-29-10003 (АААА-А19-119100890052-8) |
5 | National Science Foundation | CHE-1904780 |
6 | Russian Foundation for Basic Research | 19-33-60045 |
7 | National Institutes of Health | 1R21HL154032-01 |
8 | Ministry of Science and Higher Education of the Russian Federation | 0239-2021-0002 |
Abstract:
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.
Cite:
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
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
Dates:
Submitted: | Feb 26, 2021 |
Accepted: | Apr 30, 2021 |
Published online: | Apr 30, 2021 |
Published print: | Jul 2, 2021 |
Identifiers:
Web of science | WOS:000655533000001 |
Scopus | 2-s2.0-85106652401 |
Elibrary | 46085696 |
Chemical Abstracts | 2021:1189529 |
PMID | 33929077 |
OpenAlex | W3158727826 |