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

The Journal of Physical Chemistry. C, Nanomaterials and Interfaces
Oleg G SalnikovEduard Y Chekmenev

Abstract

13C-hyperpolarized carboxylates, such as pyruvate and acetate, are emerging molecular contrast agents for 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 aqueous phase using homogeneous hydrogenation with parahydrogen over water-soluble rhodium catalyst. 13C polarization of 0.82% and 2.1% was 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.

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Citations

Dec 5, 2019·Analytical Chemistry·Baptiste JoallandEduard Y Chekmenev
Nov 11, 2020·Analytical Chemistry·Jonathan R BirchallEduard Y Chekmenev
May 1, 2021·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Sylwia J OstrowskaMarcel Utz
Feb 27, 2021·Angewandte Chemie·Andrey N PravdivtsevJan-Bernd Hövener
May 6, 2021·Magnetic Resonance in Chemistry : MRC·Baptiste JoallandEduard Y Chekmenev

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