ParaHydrogen Polarized Ethyl-[1-(13) C]pyruvate in Water, a Key Substrate for Fostering the PHIP-SAH Approach to Metabolic Imaging(138 views) Carrera C, Cavallari E, Digilio G, Bondar O, Aime S, Reineri F
Chemphyschem (ISSN: 1439-4235linking, 1439-7641), 2021 Mar 15; 22(11): 1042-1048.
Paper type: Journal Article, Research Support, Non-U. S. Gov'T,
Impact factor: 3.144, 5-year impact factor: 3.858
Url: Not available.
Keywords: Hyperpolarization, Nuclear Magnetic Resonance, Para-Hydrogen, Pyruvate, Carbon Isotopes
, Hydrogen Chemistry
, Hydrogenation
, Magnetic Resonance Spectroscopy
, Molecular Structure
, Pyruvates Chemistry
, Water Chemistry,
Affiliations: *** IBB - CNR ***
Institute of Biostructures and Bioimaging, National Research Council, Via Nizza 52, 10126, Torino, Italy.
Department of Molecular Biotechnology and Health Sciences Molecular Imaging Centre, University of Torino, Via Nizza 52, 10126, Torino, Italy.
Department of Science and Technologic Innovation, Università del Piemonte Orientale "A. Avogadro", Viale Teresa Michel 11, 15121, Alessandria, Italy.
References: Not available.
ParaHydrogen Polarized Ethyl-[1-(13) C]pyruvate in Water, a Key Substrate for Fostering the PHIP-SAH Approach to Metabolic Imaging
An efficient synthesis of vinyl-[1-(13) C]pyruvate has been reported, from which (13) C hyperpolarized (HP) ethyl-[1-(13) C]pyruvate has been obtained by means of ParaHydrogen Induced Polarization (PHIP). Due to the intrinsic lability of pyruvate, which leads quickly to degradation of the reaction mixture even under mild reaction conditions, the vinyl-ester has been synthesized through the intermediacy of a more stable ketal derivative. (13) C and (1) H hyperpolarizations of ethyl-[1-(13) C]pyruvate, hydrogenated using ParaHydrogen, have been compared to those observed on the more widely used allyl-derivative. It has been demonstrated that the spin order transfer from ParaHydrogen protons to (13) C, is more efficient on the ethyl than on the allyl-esterdue to the larger J-couplings involved. The main requirements needed for the biological application of this HP product have been met, i. e. an aqueous solution of the product at high concentration (40 mM) with a good (13) C polarization level (4.8 %) has been obtained. The in vitro metabolic transformation of the HP ethyl-[1-(13) C]pyruvate, catalyzed by an esterase, has been observed. This substrate appears to be a good candidate for in vivo metabolic investigations using PHIP hyperpolarized probes.
ParaHydrogen Polarized Ethyl-[1-(13) C]pyruvate in Water, a Key Substrate for Fostering the PHIP-SAH Approach to Metabolic Imaging
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