Simple Esterification of [1-13C]-Alpha-Ketoglutarate Enhances Membrane Permeability and Allows for Noninvasive Tracing of Glutamate and Glutamine Production

ACS Chem Biol. 2021 Nov 19;16(11):2144-2150. doi: 10.1021/acschembio.1c00561. Epub 2021 Sep 23.

Abstract

Alpha-ketoglutarate (α-KG) is a key metabolite and signaling molecule in cancer cells, but the low permeability of α-KG limits the study of α-KG mediated effects in vivo. Recently, cell-permeable monoester and diester α-KG derivatives have been synthesized for use in vivo, but many of these derivatives are not compatible for use in hyperpolarized carbon-13 nuclear magnetic resonance spectroscopy (HP-13C-MRS). HP-13C-MRS is a powerful technique that has been used to noninvasively trace labeled metabolites in real time. Here, we show that using diethyl-[1-13C]-α-KG as a probe in HP-13C-MRS allows for noninvasive tracing of α-KG metabolism in vivo.

Publication types

  • Research Support, N.I.H., Intramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biological Transport
  • Carbon Isotopes
  • Cell Line, Tumor
  • Cell Membrane / drug effects*
  • Glutamic Acid / genetics
  • Glutamic Acid / metabolism*
  • Glutamine / genetics
  • Glutamine / metabolism*
  • HCT116 Cells
  • Humans
  • Ketoglutaric Acids / metabolism*
  • Mice
  • Mice, Nude
  • Neoplasms, Experimental
  • Permeability

Substances

  • Carbon Isotopes
  • Ketoglutaric Acids
  • Glutamine
  • Glutamic Acid