Toward Cleavable Metabolic/pH Sensing “Double Agents” Hyperpolarized by NMR Signal Amplification by Reversible Exchange

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  • Bryce E. Kidd
    Department of Chemistry and Biochemistry Southern Illinois University Carbondale IL 62901 USA
  • Jamil A. Mashni
    Department of Chemistry and Biochemistry Southern Illinois University Carbondale IL 62901 USA
  • Miranda N. Limbach
    Department of Chemistry and Biochemistry Southern Illinois University Carbondale IL 62901 USA
  • Fan Shi
    Department of Chemistry and Biochemistry Southern Illinois University Carbondale IL 62901 USA
  • Eduard Y. Chekmenev
    Department of Chemistry, Integrative Biosciences (Ibio) Wayne State University, Karmanos Cancer Institute (KCI) Detroit MI 48202 USA
  • Yuqing Hou
    Department of Chemistry and Biochemistry Southern Illinois University Carbondale IL 62901 USA
  • Boyd M. Goodson
    Department of Chemistry and Biochemistry Southern Illinois University Carbondale IL 62901 USA

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<jats:title>Abstract</jats:title><jats:p>We show the simultaneous generation of hyperpolarized <jats:sup>13</jats:sup>C‐labeled acetate and <jats:sup>15</jats:sup>N‐labeled imidazole following spin‐relay of hyperpolarization and hydrolysis of the acetyl moiety on 1<jats:bold>–</jats:bold><jats:sup>13</jats:sup>C‐<jats:sup>15</jats:sup>N<jats:sub>2</jats:sub>‐acetylimidazole. Using SABRE‐SHEATH (Signal Amplification by Reversible Exchange in SHield Enables Alignment Transfer to Heteronuclei), transfer of spin order occurs from parahydrogen to acetylimidazole <jats:sup>15</jats:sup>N atoms and the acetyl <jats:sup>13</jats:sup>C site (≈263‐fold enhancement), giving rise to relatively long hyperpolarization lifetimes at 0.3 T (<jats:italic>T</jats:italic><jats:sub>1</jats:sub>≈52 s and ≈149 s for <jats:sup>13</jats:sup>C and <jats:sup>15</jats:sup>N, respectively). Immediately following polarization transfer, the <jats:sup>13</jats:sup>C‐labeled acetyl group is hydrolytically cleaved to produce hyperpolarized <jats:sup>13</jats:sup>C‐acetate/acetic acid (≈140‐fold enhancement) and <jats:sup>15</jats:sup>N‐imidazole (≈180‐fold enhancement), the former with a <jats:sup>13</jats:sup>C <jats:italic>T</jats:italic><jats:sub>1</jats:sub> of ≈14 s at 0.3 T. Straightforward synthetic routes, efficient spin‐relay of SABRE hyperpolarization, and facile bond cleavage open a door to the cheap and rapid generation of long‐lived hyperpolarized states within a wide range of molecular targets, including biologically relevant carboxylic acid derivatives, for metabolic and pH imaging.</jats:p>

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