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Heterogeneous 1H and 13C Parahydrogen-Induced Polarization of Acetate and Pyruvate Esters. / Salnikov, Oleg G.; Chukanov, Nikita V.; Kovtunova, Larisa M. et al.

In: ChemPhysChem, Vol. 22, No. 13, 02.07.2021, p. 1389-1396.

Research output: Contribution to journal › Article › peer-review

Harvard

Salnikov, OG, Chukanov, NV, Kovtunova, LM, Bukhtiyarov, VI, Kovtunov, KV, Shchepin, RV, Koptyug, IV & Chekmenev, EY 2021, 'Heterogeneous 1H and 13C Parahydrogen-Induced Polarization of Acetate and Pyruvate Esters', ChemPhysChem, vol. 22, no. 13, pp. 1389-1396. https://doi.org/10.1002/cphc.202100156

APA

Salnikov, O. G., Chukanov, N. V., Kovtunova, L. M., Bukhtiyarov, V. I., Kovtunov, K. V., Shchepin, R. V., Koptyug, I. V., & Chekmenev, E. Y. (2021). Heterogeneous 1H and 13C Parahydrogen-Induced Polarization of Acetate and Pyruvate Esters. ChemPhysChem, 22(13), 1389-1396. https://doi.org/10.1002/cphc.202100156

Vancouver

Salnikov OG, Chukanov NV, Kovtunova LM, Bukhtiyarov VI, Kovtunov KV, Shchepin RV et al. Heterogeneous 1H and 13C Parahydrogen-Induced Polarization of Acetate and Pyruvate Esters. ChemPhysChem. 2021 Jul 2;22(13):1389-1396. doi: 10.1002/cphc.202100156

Author

Salnikov, Oleg G. ; Chukanov, Nikita V. ; Kovtunova, Larisa M. et al. / Heterogeneous 1H and 13C Parahydrogen-Induced Polarization of Acetate and Pyruvate Esters. In: ChemPhysChem. 2021 ; Vol. 22, No. 13. pp. 1389-1396.

BibTeX

@article{9c3e8305a3ec4f0f91c8f753db18efab,
title = "Heterogeneous 1H and 13C Parahydrogen-Induced Polarization of Acetate and Pyruvate Esters",
abstract = "Magnetic resonance imaging of [1-13C]hyperpolarized carboxylates (most notably, [1-13C]pyruvate) allows one to visualize abnormal metabolism in tumors and other pathologies. Herein, we investigate the efficiency of 1H and 13C 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 1-13C-enriched forms with parahydrogen over Rh/TiO2 catalysts in methanol-d4 and in D2O. The maximum obtained 1H polarization was 0.6±0.2 % (for propyl acetate in CD3OD), while the highest 13C polarization was 0.10±0.03 % (for ethyl acetate in CD3OD). 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 1H and 13C 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.",
keywords = "hyperpolarization, imaging agents, NMR spectroscopy, parahydrogen, PHIP",
author = "Salnikov, {Oleg G.} and Chukanov, {Nikita V.} and Kovtunova, {Larisa M.} and Bukhtiyarov, {Valerii I.} and Kovtunov, {Kirill V.} and Shchepin, {Roman V.} and Koptyug, {Igor V.} and Chekmenev, {Eduard Y.}",
note = "Funding Information: O. G. S., N. V. C., K. V. K. and I. V. K. thank the Russian Foundation for Basic Research (grants 19‐29‐10003, 19‐43‐540004, and 19‐33‐60045). L. M. K. thanks the Ministry of Science and Higher Education of the Russian Federation (project #AAAA‐A21‐121011390011‐4) for the support of catalysts{\textquoteright} preparation. E. Y. C. thanks NSF CHE‐1904780, NCI 1R21CA220137, NHLBI 1R21HL154032, and DOD CDMRP W81XWH‐12‐1‐0159/BC112431. Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",
year = "2021",
month = jul,
day = "2",
doi = "10.1002/cphc.202100156",
language = "English",
volume = "22",
pages = "1389--1396",
journal = "ChemPhysChem",
issn = "1439-4235",
publisher = "Wiley-Blackwell",
number = "13",

}

RIS

TY - JOUR

T1 - Heterogeneous 1H and 13C Parahydrogen-Induced Polarization of Acetate and Pyruvate Esters

AU - Salnikov, Oleg G.

AU - Chukanov, Nikita V.

AU - Kovtunova, Larisa M.

AU - Bukhtiyarov, Valerii I.

AU - Kovtunov, Kirill V.

AU - Shchepin, Roman V.

AU - Koptyug, Igor V.

AU - Chekmenev, Eduard Y.

N1 - Funding Information: O. G. S., N. V. C., K. V. K. and I. V. K. thank the Russian Foundation for Basic Research (grants 19‐29‐10003, 19‐43‐540004, and 19‐33‐60045). L. M. K. thanks the Ministry of Science and Higher Education of the Russian Federation (project #AAAA‐A21‐121011390011‐4) for the support of catalysts’ preparation. E. Y. C. thanks NSF CHE‐1904780, NCI 1R21CA220137, NHLBI 1R21HL154032, and DOD CDMRP W81XWH‐12‐1‐0159/BC112431. Publisher Copyright: © 2021 Wiley-VCH GmbH Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2021/7/2

Y1 - 2021/7/2

N2 - Magnetic resonance imaging of [1-13C]hyperpolarized carboxylates (most notably, [1-13C]pyruvate) allows one to visualize abnormal metabolism in tumors and other pathologies. Herein, we investigate the efficiency of 1H and 13C 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 1-13C-enriched forms with parahydrogen over Rh/TiO2 catalysts in methanol-d4 and in D2O. The maximum obtained 1H polarization was 0.6±0.2 % (for propyl acetate in CD3OD), while the highest 13C polarization was 0.10±0.03 % (for ethyl acetate in CD3OD). 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 1H and 13C 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.

AB - Magnetic resonance imaging of [1-13C]hyperpolarized carboxylates (most notably, [1-13C]pyruvate) allows one to visualize abnormal metabolism in tumors and other pathologies. Herein, we investigate the efficiency of 1H and 13C 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 1-13C-enriched forms with parahydrogen over Rh/TiO2 catalysts in methanol-d4 and in D2O. The maximum obtained 1H polarization was 0.6±0.2 % (for propyl acetate in CD3OD), while the highest 13C polarization was 0.10±0.03 % (for ethyl acetate in CD3OD). 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 1H and 13C 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.

KW - hyperpolarization

KW - imaging agents

KW - NMR spectroscopy

KW - parahydrogen

KW - PHIP

UR - http://www.scopus.com/inward/record.url?scp=85106652401&partnerID=8YFLogxK

U2 - 10.1002/cphc.202100156

DO - 10.1002/cphc.202100156

M3 - Article

C2 - 33929077

AN - SCOPUS:85106652401

VL - 22

SP - 1389

EP - 1396

JO - ChemPhysChem

JF - ChemPhysChem

SN - 1439-4235

IS - 13

ER -

ID: 28874040