3-(Benzyloxy)-1-(5-[18F]fluoropentyl)-5-nitro-1H-indazole: a PET radiotracer to measure acetylcholinesterase in brain

Future Med Chem. 2017 Jun;9(10):983-994. doi: 10.4155/fmc-2017-0023. Epub 2017 Jun 20.

Abstract

Aim: Noninvasive studies of the acetylcholinesterase (AChE) level in Alzheimer's disease (AD) patients can contribute to a better understanding of the disease and its therapeutic. We propose 3-(benzyloxy)-1-(5-[18F]fluoropentyl)-5-nitro-1H-indazole, [18F]-IND1, structurally related to the AChE-inhibitor CP126,998, as a new positron emission tomography-radiotracer.

Experimental: Radiosynthesis, with 18F, stability, lipophilicity and protein binding of [18F]-IND1 were studied. In vivo behavior, in normal mice and on AD mice models, were also analyzed.

Results: [18F]-IND1 was obtained in good radiochemical yield, was stable for at least 2 h in different conditions, and had adequate lipophilicity for blood-brain barrier penetration. Biodistribution studies, in normal mice, showed that [18F]-IND1 was retained in the brain after 1 h. In vivo tacrine-blocking experiments indicated this uptake could be specifically due to AChE interaction. Studies in transgenic AD mice showed differential, compared with normal mice, binding in many brain regions.

Conclusion: [18F]-IND1 can be used to detect AChE changes in AD patients.

Keywords: 18F; Alzheimer's disease; PET; acetylcholinesterase; brain; indazole.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / analysis*
  • Acetylcholinesterase / metabolism
  • Alzheimer Disease / diagnostic imaging*
  • Animals
  • Brain / diagnostic imaging*
  • Brain / metabolism
  • Female
  • Humans
  • Indazoles / chemical synthesis
  • Indazoles / chemistry*
  • Indazoles / pharmacokinetics
  • Mice
  • Molecular Structure
  • Positron-Emission Tomography*
  • Tissue Distribution

Substances

  • 3-(benzyloxy)-1-(5-fluoropentyl)-5-nitro-1H-indazole
  • Indazoles
  • Acetylcholinesterase