Carbon‐13 Hyperpolarization of α‐Ketocarboxylates with Parahydrogen in Reversible Exchange

McBride, Stephen J.; MacCulloch, Keilian; TomHon, Patrick; Browning, Austin; Meisel, Samantha; Abdulmojeed, Mustapha; Goodson, Boyd M.; Chekmenev, Eduard Y.; Theis, Thomas

doi:10.1002/cmdc.202400378

Title: Carbon‐13 Hyperpolarization of α‐Ketocarboxylates with Parahydrogen in Reversible Exchange

Journal Article · 09 December 2024 · ChemMedChem

DOI: https://doi.org/10.1002/cmdc.202400378 · OSTI ID:2480953

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Department of Chemistry North Carolina State University 2620 Yarbrough Dr. Raleigh, NC 27695 USA
Vizma Life Sciences 400 South Elliot Rd., Suite D-178 Chapel Hill, NC 27514 USA
School of Chemical &, Biomolecular Sciences Materials Technology Center Southern Illinois University 1245 Lincoln Dr. Carbondale, IL 62901 USA
Integrative Biosciences Department of Chemistry Karmanos Cancer Institute Wayne State University 5101 Cass Ave. Detroit, MI 48202 USA
Department of Chemistry North Carolina State University 2620 Yarbrough Dr. Raleigh, NC 27695 USA, Department of Physics North Carolina State University 2401 Stinson Dr. Raleigh, NC 27695 USA

Abstract Signal Amplification by Reversible Exchange (SABRE) is a relatively simple and fast hyperpolarization technique that has been used to hyperpolarize the α‐ketocarboxylate pyruvate, a central metabolite and the leading hyperpolarized MRI contrast agent. In this work, we show that SABRE can readily be extended to hyperpolarize ¹³ C nuclei at natural abundance on many other α‐ketocarboxylates. Hyperpolarization is observed and optimized on pyruvate (P _13C =17 %) and 2‐oxobutyrate (P _13C =25 %) with alkyl chains in the R‐group, oxaloacetate (P _13C =11 %) and alpha‐ketoglutarate (P _13C =13 %) with carboxylate moieties in the R group, and phenylpyruvate (P _13C =2 %) and phenylglyoxylate (P _13C =2 %) with phenyl rings in the R‐group. New catalytically active SABRE binding motifs of the substrates to the hyperpolarization transfer catalyst – particularly for oxaloacetate – are observed. We experimentally explore the connection between temperature and exchange rates for all of these SABRE systems and develop a theoretical kinetic model, which is used to fit the hyperpolarization build‐up and decay during SABRE activity.

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Sponsoring Organization:: USDOE

Grant/Contract Number:: NONE; SC0023334

OSTI ID:: 2480953

Journal Information:: ChemMedChem, Journal Name: ChemMedChem Journal Issue: 5 Vol. 20; ISSN 1860-7179

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: France

Language:: English

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