Ramatroban-Based Analogues Containing Fluorine Group as Potential 18F-Labeled Positron Emission Tomography (PET) G-Protein Coupled Receptor 44 (GPR44) Tracers

Molecules. 2021 Mar 6;26(5):1433. doi: 10.3390/molecules26051433.

Abstract

Diabetes remains one of the fastest growing chronic diseases and is a leading source of morbidity and accelerated mortality in the world. Loss of beta cell mass (BCM) and decreased sensitivity to insulin underlie diabetes pathogenesis. Yet, the ability to safely and directly assess BCM in individuals with diabetes does not exist. Measures such as blood glucose provide only a crude indirect picture of beta cell health. PET imaging could, in theory, allow for safe, direct, and precise characterization of BCM. However, identification of beta cell-specific radiolabeled tracers remains elusive. G-protein coupled receptor 44 (GPR44) is a transmembrane protein that was characterized in 2012 as highly beta cell-specific within the insulin-positive islets of Langerhans. Accordingly, radiolabeling of existing GPR44 antagonists could be a viable method to accelerate PET tracer development. The present study aims to evaluate and summarize published analogues of the GPR44 antagonist ramatroban to develop 18F-labeled PET tracers for BCM analysis. The 77 corresponding ramatroban analogues containing a fluorine nuclide were characterized for properties including binding affinity, selectivity, and pharmacokinetic and metabolic profile, and 32 compounds with favorable properties were identified. This review illustrates the potential of GPR44 analogues for the development of PET tracers.

Keywords: 18F-labeling; CRTH2; G-protein coupled receptor 44 (GPR44); PET probes; beta cell imaging; beta cell mass (BCM); diabetes; pancreatic islets; positron emission tomography (PET); ramatroban analogues.

Publication types

  • Review

MeSH terms

  • Carbazoles / chemistry*
  • Fluorine Radioisotopes / metabolism*
  • Humans
  • Insulin-Secreting Cells / chemistry
  • Insulin-Secreting Cells / cytology
  • Insulin-Secreting Cells / metabolism*
  • Platelet Aggregation Inhibitors / chemistry
  • Positron-Emission Tomography / methods*
  • Radioactive Tracers*
  • Radiopharmaceuticals / metabolism*
  • Receptors, Immunologic / metabolism*
  • Receptors, Prostaglandin / metabolism*
  • Sulfonamides / chemistry*

Substances

  • Carbazoles
  • Fluorine Radioisotopes
  • Platelet Aggregation Inhibitors
  • Radioactive Tracers
  • Radiopharmaceuticals
  • Receptors, Immunologic
  • Receptors, Prostaglandin
  • Sulfonamides
  • ramatroban
  • prostaglandin D2 receptor