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Parahydrogen-Induced Polarization of 1-13C-Acetates and 1-13C-Pyruvates Using Sidearm Hydrogenation of Vinyl, Allyl, and Propargyl Esters. / Salnikov, Oleg G.; Chukanov, Nikita V.; Shchepin, Roman V. et al.

In: Journal of Physical Chemistry C, Vol. 123, No. 20, 23.05.2019, p. 12827-12840.

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

Harvard

Salnikov, OG, Chukanov, NV, Shchepin, RV, Manzanera Esteve, IV, Kovtunov, KV, Koptyug, IV & Chekmenev, EY 2019, 'Parahydrogen-Induced Polarization of 1-13C-Acetates and 1-13C-Pyruvates Using Sidearm Hydrogenation of Vinyl, Allyl, and Propargyl Esters', Journal of Physical Chemistry C, vol. 123, no. 20, pp. 12827-12840. https://doi.org/10.1021/acs.jpcc.9b02041

APA

Salnikov, O. G., Chukanov, N. V., Shchepin, R. V., Manzanera Esteve, I. V., Kovtunov, K. V., Koptyug, I. V., & Chekmenev, E. Y. (2019). Parahydrogen-Induced Polarization of 1-13C-Acetates and 1-13C-Pyruvates Using Sidearm Hydrogenation of Vinyl, Allyl, and Propargyl Esters. Journal of Physical Chemistry C, 123(20), 12827-12840. https://doi.org/10.1021/acs.jpcc.9b02041

Vancouver

Salnikov OG, Chukanov NV, Shchepin RV, Manzanera Esteve IV, Kovtunov KV, Koptyug IV et al. Parahydrogen-Induced Polarization of 1-13C-Acetates and 1-13C-Pyruvates Using Sidearm Hydrogenation of Vinyl, Allyl, and Propargyl Esters. Journal of Physical Chemistry C. 2019 May 23;123(20):12827-12840. doi: 10.1021/acs.jpcc.9b02041

Author

Salnikov, Oleg G. ; Chukanov, Nikita V. ; Shchepin, Roman V. et al. / Parahydrogen-Induced Polarization of 1-13C-Acetates and 1-13C-Pyruvates Using Sidearm Hydrogenation of Vinyl, Allyl, and Propargyl Esters. In: Journal of Physical Chemistry C. 2019 ; Vol. 123, No. 20. pp. 12827-12840.

BibTeX

@article{1866ce9777ae4f80b6451e8bbf34710f,
title = "Parahydrogen-Induced Polarization of 1-13C-Acetates and 1-13C-Pyruvates Using Sidearm Hydrogenation of Vinyl, Allyl, and Propargyl Esters",
abstract = "13C-hyperpolarized carboxylates, such as pyruvate and acetate, are emerging molecular contrast agents for magnetic resonance imaging (MRI) visualization of various diseases, including cancer. Here, we present a systematic study of 1H and 13C parahydrogen-induced polarization of acetate and pyruvate esters with ethyl, propyl, and allyl alcoholic moieties. It was found that allyl pyruvate is the most efficiently hyperpolarized compound from those under study, yielding 21 and 5.4% polarization of 1H and 13C nuclei, respectively, in CD3OD solutions. Allyl pyruvate and ethyl acetate were also hyperpolarized in the aqueous phase using homogeneous hydrogenation with parahydrogen over a water-soluble rhodium catalyst. 13C polarization values of 0.82 and 2.1% were obtained for allyl pyruvate and ethyl acetate, respectively. 13C-hyperpolarized methanolic and aqueous solutions of allyl pyruvate and ethyl acetate were employed for in vitro MRI visualization, demonstrating the prospects for translation of the presented approach to biomedical in vivo studies.",
keywords = "MAGNETIC-RESONANCE, IN-VIVO, SPIN ORDER, HYPERPOLARIZATION, PHIP, TRANSFORMATION, METABOLITES, PRECURSORS, PYRUVATE, LACTATE",
author = "Salnikov, {Oleg G.} and Chukanov, {Nikita V.} and Shchepin, {Roman V.} and {Manzanera Esteve}, {Isaac V.} and Kovtunov, {Kirill V.} and Koptyug, {Igor V.} and Chekmenev, {Eduard Y.}",
year = "2019",
month = may,
day = "23",
doi = "10.1021/acs.jpcc.9b02041",
language = "English",
volume = "123",
pages = "12827--12840",
journal = "Journal of Physical Chemistry C",
issn = "1932-7447",
publisher = "American Chemical Society",
number = "20",

}

RIS

TY - JOUR

T1 - Parahydrogen-Induced Polarization of 1-13C-Acetates and 1-13C-Pyruvates Using Sidearm Hydrogenation of Vinyl, Allyl, and Propargyl Esters

AU - Salnikov, Oleg G.

AU - Chukanov, Nikita V.

AU - Shchepin, Roman V.

AU - Manzanera Esteve, Isaac V.

AU - Kovtunov, Kirill V.

AU - Koptyug, Igor V.

AU - Chekmenev, Eduard Y.

PY - 2019/5/23

Y1 - 2019/5/23

N2 - 13C-hyperpolarized carboxylates, such as pyruvate and acetate, are emerging molecular contrast agents for magnetic resonance imaging (MRI) visualization of various diseases, including cancer. Here, we present a systematic study of 1H and 13C parahydrogen-induced polarization of acetate and pyruvate esters with ethyl, propyl, and allyl alcoholic moieties. It was found that allyl pyruvate is the most efficiently hyperpolarized compound from those under study, yielding 21 and 5.4% polarization of 1H and 13C nuclei, respectively, in CD3OD solutions. Allyl pyruvate and ethyl acetate were also hyperpolarized in the aqueous phase using homogeneous hydrogenation with parahydrogen over a water-soluble rhodium catalyst. 13C polarization values of 0.82 and 2.1% were obtained for allyl pyruvate and ethyl acetate, respectively. 13C-hyperpolarized methanolic and aqueous solutions of allyl pyruvate and ethyl acetate were employed for in vitro MRI visualization, demonstrating the prospects for translation of the presented approach to biomedical in vivo studies.

AB - 13C-hyperpolarized carboxylates, such as pyruvate and acetate, are emerging molecular contrast agents for magnetic resonance imaging (MRI) visualization of various diseases, including cancer. Here, we present a systematic study of 1H and 13C parahydrogen-induced polarization of acetate and pyruvate esters with ethyl, propyl, and allyl alcoholic moieties. It was found that allyl pyruvate is the most efficiently hyperpolarized compound from those under study, yielding 21 and 5.4% polarization of 1H and 13C nuclei, respectively, in CD3OD solutions. Allyl pyruvate and ethyl acetate were also hyperpolarized in the aqueous phase using homogeneous hydrogenation with parahydrogen over a water-soluble rhodium catalyst. 13C polarization values of 0.82 and 2.1% were obtained for allyl pyruvate and ethyl acetate, respectively. 13C-hyperpolarized methanolic and aqueous solutions of allyl pyruvate and ethyl acetate were employed for in vitro MRI visualization, demonstrating the prospects for translation of the presented approach to biomedical in vivo studies.

KW - MAGNETIC-RESONANCE

KW - IN-VIVO

KW - SPIN ORDER

KW - HYPERPOLARIZATION

KW - PHIP

KW - TRANSFORMATION

KW - METABOLITES

KW - PRECURSORS

KW - PYRUVATE

KW - LACTATE

UR - http://www.scopus.com/inward/record.url?scp=85066123307&partnerID=8YFLogxK

U2 - 10.1021/acs.jpcc.9b02041

DO - 10.1021/acs.jpcc.9b02041

M3 - Article

C2 - 31363383

AN - SCOPUS:85066123307

VL - 123

SP - 12827

EP - 12840

JO - Journal of Physical Chemistry C

JF - Journal of Physical Chemistry C

SN - 1932-7447

IS - 20

ER -

ID: 20162336