Synthesis and evaluation of 18F-labeled mitiglinide derivatives as positron emission tomography tracers for β-cell imaging

Bioorg Med Chem. 2014 Jul 1;22(13):3270-8. doi: 10.1016/j.bmc.2014.04.059. Epub 2014 May 6.

Abstract

Measuring changes in β-cell mass in vivo during progression of diabetes mellitus is important for understanding the pathogenesis, facilitating early diagnosis, and developing novel therapeutics for this disease. However, a non-invasive method has not been developed. A novel series of mitiglinide derivatives (o-FMIT, m-FMIT and p-FMIT; FMITs) were synthesized and their binding affinity for the sulfonylurea receptor 1 (SUR1) of pancreatic islets were evaluated by inhibition studies. (+)-(S)-o-FMIT had the highest affinity of our synthesized FMITs (IC50=1.8μM). (+)-(S)-o-[(18)F]FMIT was obtained with radiochemical yield of 18% by radiofluorination of racemic precursor 7, hydrolysis, and optical resolution with chiral HPLC; its radiochemical purity was >99%. In biodistribution experiments using normal mice, (+)-(S)-o-[(18)F]FMIT showed 1.94±0.42% ID/g of pancreatic uptake at 5min p.i., and decreases in radioactivity in the liver (located close to the pancreas) was relatively rapid. Ex vivo autoradiography experiments using pancreatic sections confirmed accumulation of (+)-(S)-o-[(18)F]FMIT in pancreatic β-cells. These results suggest that (+)-(S)-o-[(18)F]FMIT meets the basic requirements for an radiotracer, and could be a candidate positron emission tomography tracer for in vivo imaging of pancreatic β-cells.

Keywords: (18)F; Mitiglinide; Positron emission tomography tracers; Sulfonylurea receptor 1.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Dose-Response Relationship, Drug
  • Fluorine Radioisotopes / chemistry
  • Fluorine Radioisotopes / pharmacology*
  • Glyburide / antagonists & inhibitors*
  • Insulin-Secreting Cells / cytology
  • Insulin-Secreting Cells / drug effects*
  • Isoindoles / chemical synthesis
  • Isoindoles / chemistry
  • Isoindoles / pharmacology*
  • Mice
  • Mice, Inbred Strains
  • Molecular Structure
  • Positron-Emission Tomography*
  • Structure-Activity Relationship
  • Tissue Distribution

Substances

  • Fluorine Radioisotopes
  • Isoindoles
  • mitiglinide
  • Glyburide