Effect of the prosthetic group on the pharmacologic properties of 18F-labeled rhodamine B, a potential myocardial perfusion agent for positron emission tomography (PET)

J Med Chem. 2012 Dec 27;55(24):11004-12. doi: 10.1021/jm301453p. Epub 2012 Dec 14.

Abstract

We recently reported the development of the 2-[(18)F]fluoroethyl ester of rhodamine B as a potential positron emission tomography (PET) tracer for myocardial perfusion imaging. This compound, which was prepared using a [(18)F]fluoroethyl prosthetic group, has significant uptake in the myocardium in rats but also demonstrates relatively high liver uptake and is rapidly hydrolyzed in vivo in mice. We have now prepared (18)F-labeled rhodamine B using three additional prosthetic groups (propyl, diethylene glycol, and triethylene glycol) and found that the prosthetic group has a significant effect on the in vitro and in vivo properties of these compounds. Of the esters prepared to date, the diethylene glycol ester is superior in terms of in vitro stability and pharmacokinetics. These observations suggest that the prosthetic group plays a significant role in determining the pharmacological properties of (18)F-labeled compounds. They also support the value of continued investigation of (18)F-labeled rhodamines as PET radiopharmaceuticals for myocardial perfusion imaging.

Publication types

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

MeSH terms

  • Animals
  • Esters
  • Fluorine Radioisotopes
  • Glycols / chemistry
  • Heart / diagnostic imaging*
  • Humans
  • Mice
  • Myocardial Perfusion Imaging*
  • Myocardium / metabolism
  • Positron-Emission Tomography
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / chemistry
  • Radiopharmaceuticals / pharmacokinetics
  • Rats
  • Rhodamines / chemical synthesis*
  • Rhodamines / chemistry
  • Rhodamines / pharmacokinetics
  • Structure-Activity Relationship
  • Tissue Distribution

Substances

  • Esters
  • Fluorine Radioisotopes
  • Glycols
  • Radiopharmaceuticals
  • Rhodamines
  • rhodamine B