High Enantiomeric Excess In-Loop Synthesis of d-[methyl-11C]Methionine for Use as a Diagnostic Positron Emission Tomography Radiotracer in Bacterial Infection

ACS Infect Dis. 2020 Jan 10;6(1):43-49. doi: 10.1021/acsinfecdis.9b00196. Epub 2019 Nov 21.

Abstract

Currently, there exists no accurate, noninvasive clinical imaging method to detect living bacteria in vivo. Our goal is to provide a positron emission tomography (PET) method to image infection by targeting bacteria-specific metabolism. Standard of care methodologies detect morphologic changes, image immunologic response to infection, or employ invasive tissue sampling with associated patient morbidity. These strategies, however, are not specific for living bacteria and are often inadequate to detect bacterial infection during fever workup. As such, there is an unmet clinical need to identify and validate new imaging tools suitable for noninvasive, in vivo (PET) imaging of living bacteria. We have shown that d-[methyl-11C]methionine (d-[11C]Met) can distinguish active bacterial infection from sterile inflammation in a murine infection model and is sensitive to both Gram-positive and Gram-negative bacteria. Here, we report an automated and >99% enantiomeric excess (ee) synthesis of d-[11C]Met from a linear d-homocysteine precursor, a significant improvement over the previously reported synthesis utilizing a d-homocysteine thiolactone hydrochloride precursor with approximately 75-85% ee. Furthermore, we took additional steps toward applying d-[11C]Met to infected patients. d-[11C]Met was subject to a panel of clinically relevant bacterial strains and demonstrated promising sensitivity to these pathogens. Finally, we performed radiation dosimetry in a normal murine cohort to set the stage for translation to humans in the near future.

Keywords: PET; d-amino acid; infection; positron emission tomography; radiochemistry.

Publication types

  • Letter
  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Bacteria / metabolism*
  • Bacterial Infections / diagnostic imaging*
  • Bacterial Infections / microbiology
  • Carbon Radioisotopes / administration & dosage
  • Carbon Radioisotopes / pharmacokinetics
  • Female
  • Humans
  • Male
  • Methionine / chemical synthesis*
  • Methionine / pharmacokinetics
  • Mice
  • Positron-Emission Tomography*
  • Radioactive Tracers*
  • Radiochemistry

Substances

  • Carbon Radioisotopes
  • Radioactive Tracers
  • Methionine