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Synthesis of unsaturated precursors for parahydrogen-induced polarization and molecular imaging of 1-13C-Acetates and 1-13C-pyruvates via side arm hydrogenation. / Chukanov, Nikita V.; Salnikov, Oleg G.; Shchepin, Roman V. et al.

In: ACS Omega, Vol. 3, No. 6, 30.06.2018, p. 6673-6682.

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

Harvard

Chukanov, NV, Salnikov, OG, Shchepin, RV, Kovtunov, KV, Koptyug, IV & Chekmenev, EY 2018, 'Synthesis of unsaturated precursors for parahydrogen-induced polarization and molecular imaging of 1-13C-Acetates and 1-13C-pyruvates via side arm hydrogenation', ACS Omega, vol. 3, no. 6, pp. 6673-6682. https://doi.org/10.1021/acsomega.8b00983

APA

Chukanov, N. V., Salnikov, O. G., Shchepin, R. V., Kovtunov, K. V., Koptyug, I. V., & Chekmenev, E. Y. (2018). Synthesis of unsaturated precursors for parahydrogen-induced polarization and molecular imaging of 1-13C-Acetates and 1-13C-pyruvates via side arm hydrogenation. ACS Omega, 3(6), 6673-6682. https://doi.org/10.1021/acsomega.8b00983

Vancouver

Chukanov NV, Salnikov OG, Shchepin RV, Kovtunov KV, Koptyug IV, Chekmenev EY. Synthesis of unsaturated precursors for parahydrogen-induced polarization and molecular imaging of 1-13C-Acetates and 1-13C-pyruvates via side arm hydrogenation. ACS Omega. 2018 Jun 30;3(6):6673-6682. doi: 10.1021/acsomega.8b00983

Author

Chukanov, Nikita V. ; Salnikov, Oleg G. ; Shchepin, Roman V. et al. / Synthesis of unsaturated precursors for parahydrogen-induced polarization and molecular imaging of 1-13C-Acetates and 1-13C-pyruvates via side arm hydrogenation. In: ACS Omega. 2018 ; Vol. 3, No. 6. pp. 6673-6682.

BibTeX

@article{5d9f75df9a8240b6a517e46335bd8f6a,
title = "Synthesis of unsaturated precursors for parahydrogen-induced polarization and molecular imaging of 1-13C-Acetates and 1-13C-pyruvates via side arm hydrogenation",
abstract = "Hyperpolarized forms of 1-13C-Acetates and 1-13C-pyruvates are used as diagnostic contrast agents for molecular imaging of many diseases and disorders. Here, we report the synthetic preparation of 1-13C isotopically enriched and pure from solvent acetates and pyruvates derivatized with unsaturated ester moiety. The reported unsaturated precursors can be employed for NMR hyperpolarization of 1-13Cacetates and 1-13C-pyruvates via parahydrogen-induced polarization (PHIP). In this PHIP variant, Side arm hydrogenation (SAH) of unsaturated ester moiety is followed by the polarization transfer from nascent parahydrogen protons to 13C nucleus via magnetic field cycling procedure to achieve hyperpolarization of 13C nuclear spins. This work reports the synthesis of PHIP-SAH precursors: vinyl 1-13C-Acetate (55% yield), allyl 1-13C-Acetate (70% yield), propargyl 1-13C-Acetate (45% yield), allyl 1-13C-pyruvate (60% yield), and propargyl 1-13C-pyruvate (35% yield). Feasibility of PHIP-SAH 13C hyperpolarization was verified by 13C NMR spectroscopy: hyperpolarized allyl 1-13C-pyruvate was produced from propargyl 1-13C-pyruvate with 13C polarization of ∼3.2% in CD3OD and ∼0.7% in D2O. 13C magnetic resonance imaging is demonstrated with hyperpolarized 1-13C-pyruvate in aqueous medium.",
keywords = "C-13 POLARIZATION, HYPERPOLARIZED MAGNETIC-RESONANCE, IN-VIVO, ORDER TRANSFER, PASADENA HYPERPOLARIZATION, PYRUVATE, SIGNAL AMPLIFICATION, SOLUBILITY, SPIN ORDER, TRANSFORMATION",
author = "Chukanov, {Nikita V.} and Salnikov, {Oleg G.} and Shchepin, {Roman V.} and Kovtunov, {Kirill V.} and Koptyug, {Igor V.} and Chekmenev, {Eduard Y.}",
note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",
year = "2018",
month = jun,
day = "30",
doi = "10.1021/acsomega.8b00983",
language = "English",
volume = "3",
pages = "6673--6682",
journal = "ACS Omega",
issn = "2470-1343",
publisher = "American Chemical Society",
number = "6",

}

RIS

TY - JOUR

T1 - Synthesis of unsaturated precursors for parahydrogen-induced polarization and molecular imaging of 1-13C-Acetates and 1-13C-pyruvates via side arm hydrogenation

AU - Chukanov, Nikita V.

AU - Salnikov, Oleg G.

AU - Shchepin, Roman V.

AU - Kovtunov, Kirill V.

AU - Koptyug, Igor V.

AU - Chekmenev, Eduard Y.

N1 - Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/6/30

Y1 - 2018/6/30

N2 - Hyperpolarized forms of 1-13C-Acetates and 1-13C-pyruvates are used as diagnostic contrast agents for molecular imaging of many diseases and disorders. Here, we report the synthetic preparation of 1-13C isotopically enriched and pure from solvent acetates and pyruvates derivatized with unsaturated ester moiety. The reported unsaturated precursors can be employed for NMR hyperpolarization of 1-13Cacetates and 1-13C-pyruvates via parahydrogen-induced polarization (PHIP). In this PHIP variant, Side arm hydrogenation (SAH) of unsaturated ester moiety is followed by the polarization transfer from nascent parahydrogen protons to 13C nucleus via magnetic field cycling procedure to achieve hyperpolarization of 13C nuclear spins. This work reports the synthesis of PHIP-SAH precursors: vinyl 1-13C-Acetate (55% yield), allyl 1-13C-Acetate (70% yield), propargyl 1-13C-Acetate (45% yield), allyl 1-13C-pyruvate (60% yield), and propargyl 1-13C-pyruvate (35% yield). Feasibility of PHIP-SAH 13C hyperpolarization was verified by 13C NMR spectroscopy: hyperpolarized allyl 1-13C-pyruvate was produced from propargyl 1-13C-pyruvate with 13C polarization of ∼3.2% in CD3OD and ∼0.7% in D2O. 13C magnetic resonance imaging is demonstrated with hyperpolarized 1-13C-pyruvate in aqueous medium.

AB - Hyperpolarized forms of 1-13C-Acetates and 1-13C-pyruvates are used as diagnostic contrast agents for molecular imaging of many diseases and disorders. Here, we report the synthetic preparation of 1-13C isotopically enriched and pure from solvent acetates and pyruvates derivatized with unsaturated ester moiety. The reported unsaturated precursors can be employed for NMR hyperpolarization of 1-13Cacetates and 1-13C-pyruvates via parahydrogen-induced polarization (PHIP). In this PHIP variant, Side arm hydrogenation (SAH) of unsaturated ester moiety is followed by the polarization transfer from nascent parahydrogen protons to 13C nucleus via magnetic field cycling procedure to achieve hyperpolarization of 13C nuclear spins. This work reports the synthesis of PHIP-SAH precursors: vinyl 1-13C-Acetate (55% yield), allyl 1-13C-Acetate (70% yield), propargyl 1-13C-Acetate (45% yield), allyl 1-13C-pyruvate (60% yield), and propargyl 1-13C-pyruvate (35% yield). Feasibility of PHIP-SAH 13C hyperpolarization was verified by 13C NMR spectroscopy: hyperpolarized allyl 1-13C-pyruvate was produced from propargyl 1-13C-pyruvate with 13C polarization of ∼3.2% in CD3OD and ∼0.7% in D2O. 13C magnetic resonance imaging is demonstrated with hyperpolarized 1-13C-pyruvate in aqueous medium.

KW - C-13 POLARIZATION

KW - HYPERPOLARIZED MAGNETIC-RESONANCE

KW - IN-VIVO

KW - ORDER TRANSFER

KW - PASADENA HYPERPOLARIZATION

KW - PYRUVATE

KW - SIGNAL AMPLIFICATION

KW - SOLUBILITY

KW - SPIN ORDER

KW - TRANSFORMATION

UR - http://www.scopus.com/inward/record.url?scp=85051232031&partnerID=8YFLogxK

U2 - 10.1021/acsomega.8b00983

DO - 10.1021/acsomega.8b00983

M3 - Article

C2 - 29978146

AN - SCOPUS:85051232031

VL - 3

SP - 6673

EP - 6682

JO - ACS Omega

JF - ACS Omega

SN - 2470-1343

IS - 6

ER -

ID: 17233869