Radiofluorinated histamine H₃ receptor antagonist as a potential probe for in vivo PET imaging: radiosynthesis and pharmacological evaluation

Bioorg Med Chem. 2012 May 1;20(9):2889-96. doi: 10.1016/j.bmc.2012.03.024. Epub 2012 Mar 17.

Abstract

The histamine H(3) receptor (H(3)R) plays a role in cognition and memory processes and is implicated in different neurological disorders, including Alzheimer's disease, schizophrenia, and narcolepsy. In vivo studies of the H(3)R occupancy using a radiolabeled PET tracer would be very useful for CNS drug discovery and development. We report here the radiosynthesis, in vitro and in vivo evaluation of a novel (18)F-labeled high-affinity H(3)R antagonist (18)F-ST889. The radiosynthesis was accomplished via nucleophilic substitution of the mesylate leaving group with a radiochemical yield of 8-20%, radiochemical purity >99%, and specific radioactivity > 65 GBq/μmol. (18)F-ST889 exhibited high in vivo stability and rather low lipophilicity (logD(7.4)=0.35 ± 0.09). In vitro autoradiography showed specific binding in H(3)R-rich brain regions such as striatum and cortex. However, in vivo PET imaging of the rat brain with (18)F-ST889 was not successful. Possible reasons are discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / metabolism
  • Animals
  • Brain / diagnostic imaging
  • Cell Line
  • Dogs
  • Drug Stability
  • Fluorine Radioisotopes / chemistry
  • Histamine H3 Antagonists / chemical synthesis*
  • Histamine H3 Antagonists / chemistry
  • Humans
  • Isotope Labeling
  • Male
  • Microsomes, Liver / metabolism
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Positron-Emission Tomography
  • Protein Binding
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / chemistry
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Histamine H3 / chemistry*
  • Receptors, Histamine H3 / metabolism

Substances

  • 18F-ST889
  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • Fluorine Radioisotopes
  • Histamine H3 Antagonists
  • Piperidines
  • Radiopharmaceuticals
  • Receptors, Histamine H3